Cottages for October Half Term on the Isle of Wight
Pack your bags and round up the kids, an autumn holiday on the Isle of Wight is beckoning. Giving you something special to look forward to this October half term, all of our Isle of Wight cottages perfectly combine homely touches with modern luxuries. Take a look through our collection and find the one just right for you. The holiday of a lifetime is but moments away.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.102 luxury cottages for October half term on the Isle of Wight
7 nights from £1081
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1081
7 nights from £648 *
48 Solent View
58283 bedroom self catering cottage with sea views in Seaview.
Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...
7 nights from £648 *
7 nights from £1050
Pucks Oak
56984 bedroom, dog friendly holiday cottage with sea views in Seaview.
Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...
7 nights from £1050
7 nights from £1836 *
Pepita
57195 bedroom, dog friendly holiday cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1836 *
7 nights from £1043
The Dairy
56313 bedroom self catering cottage near the beach in Seaview.
Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...
7 nights from £1043
From £85 per night
Sunrise and Stars
5672Dog friendly shepherds hut with a hot tub and use of pool, near Ventnor.
Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...
From £85 per night
7 nights from £950 *
Tangle Cottage
56694 bedroom self catering cottage near the beach in Seaview.
Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...
7 nights from £950 *
7 nights from £908 *
Inglefield
56374 bedroom, dog friendly holiday cottage near the beach in St Helens.
This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...
7 nights from £908 *
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £732 *
Escape Away
56122 bedroom self catering cottage near the beach in Freshwater.
Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...
7 nights from £732 *
7 nights from £656 *
Driftwood
56132 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as much as you do. Th...
7 nights from £656 *
Colwell Bay Cottages
7 nights from £1388
7 nights from £1463 *
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lon...
7 nights from £1463 *
7 nights from £1608
Dar View
54584 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...
7 nights from £1608
From £145 per night
Lazydays Hideaway
53811 bedroom glamping Yurt with sea views and an outdoor bath near Ventnor, Isle of Wight.
Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...
From £145 per night
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
7 nights from £447
Berry Cabin
52862 bedroom, dog friendly, bolthole in Seaview, Isle of Wight.
What a little cutie! Berry Cabin is a delightful bolthole for four guests and one well behaved doggy looking for some summer fun! Surrounded by Hersey nature reserve and countrysid...
7 nights from £447
7 nights from £1285
Newclose Houseboat
52003 bedroom houseboat with sea views in Bembridge, Isle of Wight
Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...
7 nights from £1285
7 nights from £547
10 Bayclose
51592 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...
7 nights from £547
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50% off
15 May 2025 - 20 May 2025
£556.00 £278.00
7 nights from £803
The Drey
51393 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...
7 nights from £803
From £237 per night *
Stargazers' Retreat
5125Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...
From £237 per night *
7 nights from £721 *
Sheldonia
51093 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...
7 nights from £721 *
Choose our flexible booking option and have the ability to cancel anytime.
7 nights from £434
Sugar Beach
51022 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight
Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...
7 nights from £434
7 nights from £763 *
Underwood Cabin
49953 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
Nestled in the beautiful grounds of St Hubert's Lodge and surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful island retreat, perfectly situated be...
7 nights from £763 *
7 nights from £600
18 Seaview Bay
49961 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming, sunny apartment found in a small development, close to the villag...
7 nights from £600
7 nights from £916 *
Sea Lights
49672 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.
Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet-friendly apartment...
7 nights from £916 *
7 nights from £567
Oceanix
49001 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect seaside getaway for your next Isle of Wight holiday. The property has been though...
7 nights from £567
7 nights from £769 *
Valdora
49593 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...
7 nights from £769 *
We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.
Quality Accredited Agency
Only the highest quality of accommodation is awarded Visit England accreditation. The assessment takes place over a few days and looks at all of our policies, practices and procedures, making sure we meet a five star standard for our guests.
We set our own standards above and beyond and we’re very proud of this accolade and all it represents.
7 nights from £1130 *
Oystercatcher
48693 bedroom luxury houseboat in Bembridge, Isle of Wight.
Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...
7 nights from £1130 *
7 nights from £515
Westhill View
48822 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.
With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...
7 nights from £515
7 nights from £955 *
9 The Ruskins
48653 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
This delightful family holiday home can be found just a short stroll from the beautiful beaches of Bembridge and a wonderful array of traditional shops and restaurants. Light fille...
7 nights from £955 *
7 nights from £540
Buckland Cabin
48531 bedroom cabin near the beach in Seaview, Isle of Wight.
Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...
7 nights from £540
7 nights from £2228
Cara Cottage
48465 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Welcome to Cara Cottage, a stunning detached property located in the heart of Bembridge village. This eye-catching holiday home with soft pink 'Spanish inspired' exterior is beauti...
7 nights from £2228
7 nights from £672 *
Daisy Cottage
48242 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...
7 nights from £672 *
Each and every one of our cottages is fully equipped with everything you’ll need on holiday.
Fully equipped cottages
All of our cottages have a standard list of equipment that goes above and beyond. As well as fluffy towels and readymade beds, our bare minimum includes everything you’ll need and more, from plenty of teaspoons to added extras such as gravy boats so no matter where you stay, you’ll be able to make your favourite home-cooked dishes.
Each inventory is regularly checked and counted so you won’t be stuck without a ladle and can leave your hairdryer at home, plus you’ll find a starter set of toiletries and cleaning products so you can get on with your holiday.
7 nights from £836
Old Bembridge House
47913 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, Old Bembridge House has all the makings of a perfect holiday idyll. Laid across three floors,...
7 nights from £836
7 nights from £1837
Harbour View
47314 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...
7 nights from £1837
7 nights from £754 *
Starboard Side
47362 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...
7 nights from £754 *
7 nights from £387
1 Harrow Cottages
46421 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...
7 nights from £387
7 nights from £2796
St Andrews
46416 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.
Looking for a truly unique getaway? This beautiful, converted church offers an unforgettable Isle of Wight escape, blending historic charm with modern convenience. Perched in an el...
7 nights from £2796
7 nights from £888
Limpets
46223 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...
7 nights from £888
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
7 nights from £1136 *
Saye House
45734 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...
7 nights from £1136 *
7 nights from £2032
Redworth
45415 bedroom self catering home near the beach in Bembridge, Isle of Wight.
This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...
7 nights from £2032
7 nights from £588
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...
7 nights from £588
7 nights from £600
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...
7 nights from £600
7 nights from £603
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £603
7 nights from £603
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Pigsty is a detached barn with parking for two cars and two private seating areas along with a spacious communal area. There are two bedrooms, a double and a twin, each bea...
7 nights from £603
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
Kingston Barns
7 nights from £2394
7 nights from £1113 *
Solas
44594 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
This superb, spacious detached house close to Seaview village has wonderful sea views from the first floor open plan sitting/dining-room and balcony. Taking full advantage of the v...
7 nights from £1113 *
7 nights from £1397 *
Windy Ridge
44644 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...
7 nights from £1397 *
7 nights from £608 *
Modwena
44683 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.
This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk from the village centre and historic pier. Located on the west coast of the Isla...
7 nights from £608 *
7 nights from £662
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...
7 nights from £662
7 nights from £646
Winkle Cottage
43952 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes' walk from the centre of town, offering the perfect family holiday...
7 nights from £646
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20% off
9 May 2025 - 16 May 2025
£773.00 £618.40
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £837
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £837
7 nights from £501
Solent View Cottage
43892 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This charming two bedroom cottage is situated in the pretty coastal village of Gurnard, just outside Cowes, home to some spectacular Solent views and a prime location to watch the ...
7 nights from £501
7 nights from £824
Beggars Roost
43463 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...
7 nights from £824
7 nights from £1495 *
Dolphin Cottage
43474 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
Within a few minutes’ walk of the village centre and located on an unmade road leading to the sea, Dolphin Cottage is a simply stunning house ideally laid out to make space for all...
7 nights from £1495 *
7 nights from £1527
Fortune
43364 bedroom, dog friendly holiday houseboat with sea views in Bembridge, Isle of Wight
Step on board this simply stunning houseboat situated in the picturesque Bembridge harbour, just a short walk from Bembridge village. The beautiful bright yellow door opens to a va...
7 nights from £1527
7 nights from £1242 *
Buckland House
42904 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Tucked out of sight yet right in the heart of Seaview, Buckland House is a stunning home, beautifully renovated by the owners and just a stone's throw from the beach and local vill...
7 nights from £1242 *
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7 nights from £1116
Merivale
42404 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
This lovely, light and spacious detached house located on Fairy Road in Seaview, just a short stroll from the seafront, makes a fantastic base for a wonderful holiday on the Isle o...
7 nights from £1116
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20% off
10 May 2025 - 17 May 2025
£1394.00 £1115.20
7 nights from £870
House of Logs
42254 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday and do...
7 nights from £870
7 nights from £980
Oak Tree Cottage
42123 bedroom self catering cottage with sea views in Seaview, Isle of Wight
With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...
7 nights from £980
7 nights from £596
Grace Cottage
42091 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...
7 nights from £596
7 nights from £657
1 St Josephs
41832 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...
7 nights from £657
7 nights from £1757
Bayside House
41784 bedroom, rural self catering cottage near the beach in Yarmouth, Isle of Wight
This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes' walk to the water’s edge, a truly stunning holiday destination. The pro...
7 nights from £1757
Our guests rate us 4.8/5 on Feefo, the independent review site.
Feefo ratings
Our latest feedback on Feefo:
7 nights from £1152 *
61 Solent View
40784 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight
On the outskirts of Seaview and within a few minutes' walk from Seagrove Bay, take in the stunning sea views from not one but two balconies. 61 Solent View is a wonderful holiday h...
7 nights from £1152 *
7 nights from £907
Keepers Cottage
40704 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...
7 nights from £907
7 nights from £1182
The New House
40254 bedroom self catering cottage in Godshill, Isle of Wight
Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...
7 nights from £1182
7 nights from £823
Fernsdale
40053 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Right in the heart of Seaview village, this semi-detached property has been completely renovated with a Skandi theme to offer a wonderful place to stay on the Isle of Wight. Just a...
7 nights from £823
7 nights from £944
St Albans House
39804 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...
7 nights from £944
7 nights from £861 *
Bay View
39022 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...
7 nights from £861 *
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20% off
30 May 2025 - 6 Jun 2025
From £1170.00 £936.00
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
7 nights from £2008
Solent Heights
39465 bedroom self catering cottage near the beach in Cowes, Isle of Wight
A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...
7 nights from £2008
7 nights from £545 *
6 St Josephs
38462 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...
7 nights from £545 *
7 nights from £417
Cockleshells
38152 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The accommodation offers a double...
7 nights from £417
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20% off
10 May 2025 - 17 May 2025
From £498.00 £398.40
7 nights from £1174
Shore House
37783 bedroom self catering cottage with sea views in Seaview, Isle of Wight
A seaside sanctuary, Shore House is a beautifully decorated three-storey house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...
7 nights from £1174
7 nights from £541
2 Bermuda
35172 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Welcome to 2 Bermuda, a rather lovely first floor apartment nestled in the charming village of Seaview, with wonderful views stretching across the Solent - ideal for an unforgettab...
7 nights from £541
7 nights from £1321 *
2 Little Cedars
35204 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
2 Little Cedars is a sleek and modern property, with a light and clean finish throughout. Split over three floors, and stylishly decorated with luxury furnishings, this delightful ...
7 nights from £1321 *
7 nights from £662
2 St Josephs
35302 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
With sea views from the terrace and fresh, modern decor throughout, 2 St Josephs is a holiday maker's home-from-home. It is the perfect getaway for a small family, a couple or two ...
7 nights from £662
7 nights from £627
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...
7 nights from £627
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20% off
16 May 2025 - 23 May 2025
From £807.00 £645.60
7 nights from £779
30 Seaview Bay
35493 bedroom holiday cottage near the beach in Seaview, Isle of Wight.
If you're searching for a place to stay by the sea, 30 Seaview Bay could be just the spot. Perched just steps away from the enchanting Seagrove Bay and Seaview Bay, this sunny apar...
7 nights from £779
7 nights from £1030 *
6 Seafield Terrace
35625 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
6 Seafield Terrace is a charming, spacious terraced cottage set in the pretty village of Seaview. It would ideally suit a large family, several couples or a group of friends travel...
7 nights from £1030 *
7 nights from £695
7 Sandpipers
35683 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...
7 nights from £695
7 nights from £992 *
Alcantara
35743 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Located just a short stroll away from the beautiful beaches of Seaview, Alcantara is a magical place for a holiday. With oodles of space, stylish interiors and classic furnishings,...
7 nights from £992 *
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £768
Apt 1 Springfield Court
35752 bedroom self catering apartment near the beach in Seaview.
Apt 1 Springfield Court is a luxurious, ground floor apartment, set in an exclusive development in the picturesque village of Seaview. It would suit a small family or a couple in n...
7 nights from £768
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30% off
23 May 2025 - 30 May 2025
From £1400.00 £980.00
7 nights from £1862
Barton Manor Farmhouse
35804 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
This impressive 150 year old farmhouse sleeps eight and is the perfect location for a fabulous family gathering for all ages. Set in the breathtaking Barton Manor Estate, it is adj...
7 nights from £1862
7 nights from £745
Barton Manor Lake Cottage
35812 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...
7 nights from £745
7 nights from £780
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A warm Isle of Wight welcome awaits you at Blackberries, a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike, in the delightful sail...
7 nights from £780
7 nights from £1197
Creekside
35884 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
Creekside is a fabulous waterfront property that makes a wonderful choice of holiday home at any time of the year. This stunning detached house, set on the banks of Wootton Creek, ...
7 nights from £1197
7 nights from £584
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...
7 nights from £584
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
7 nights from £519
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...
7 nights from £519
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20% off
10 May 2025 - 17 May 2025
£644.00 £515.20
7 nights from £917
Garsdon
36044 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
This lovely bright and spacious detached house located on a quiet lane in Seaview is just a ten minute stroll from the beautiful beach at Seagrove Bay. With a charming large enclos...
7 nights from £917
7 nights from £658
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet corner of the delightful village of Seaview, Lawn end is a cosy island retreat, tastefully furnished to offer contemporary living for families or a group of ...
7 nights from £658
7 nights from £836 *
Lucaya
36214 bedroom self catering cottage near the beach in Ryde, Isle of Wight.
Welcome to Lucaya, a smart town house for eight set over three floors, a great space with a pretty enclosed rear patio and lawn, the ideal stay for a family looking for a seaside b...
7 nights from £836 *
7 nights from £917
Mallards
36275 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight.
Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...
7 nights from £917
7 nights from £1405 *
Neptune Cottage
36364 bedroom, self catering cottage near the beach in Seaview, Isle of Wight.
Just a few steps from your front door to the sea, this stunning newly refurbished seafront cottage is an exceptional place to stay in Seaview. With many of the rooms boasting wonde...
7 nights from £1405 *
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £1250
Orchard House
36414 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight
Orchard House is a wonderful property for an extended family looking for a sprawling holiday home near the beach in Bembridge. The downstairs living areas are inviting - no doubt t...
7 nights from £1250
7 nights from £600
Pandora Lodge
36423 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...
7 nights from £600
7 nights from £1590 *
Pitt Corner
36444 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is a roomy retreat, with plenty of space for the family to spread...
7 nights from £1590 *
7 nights from £557
Quiet Corner Cottage
36462 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...
7 nights from £557
7 nights from £619
Spinnakers
36592 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, semi-detached Spinnakers is situated on a small private estate w...
7 nights from £619
7 nights from £367
The Beach Retreat
36652 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated just a stone's throw away from Seaview beach, where you will discover beautiful views across the Solent, The Beach Retreat is located close to the village centre...
7 nights from £367
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
7 nights from £752
Trevenna
36863 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or couples travelling tog...
7 nights from £752
7 nights from £597
Yardley
36972 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £597
7 nights from £643
1 Starboard House
35072 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...
7 nights from £643
7 nights from £703 *
1 Thatched Cottage
35082 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...
7 nights from £703 *
