Luxury Cottages for 4 People on the Isle of Wight
Enjoy a luxury island retreat and book a holiday cottage for up to four people on the Isle of Wight. There's room for you and three of your nearest and dearest, and many of our cottages are dog-friendly too. Browse through our selection of 203 available self-catering cottages and take a step closer to the holiday of a lifetime.
Spending time with our friends and family is really important, but it's not always that easy to get together and catch up. Holiday cottages provide great neutral ground in beautiful settings, away from the distractions of everyday life. Spend time together in a luxury self catering cottage sleeping up to 4 people and rediscover yourselves.
Self Catering Cottages on the Isle of Wight for Four People
At Classic Cottages we pride ourselves on marketing only the finest holiday cottages on the Isle of Wight. Each one of our self catering cottages is personally inspected and fully equipped to ensure your total comfort. Take your time looking through our collection of 203 available holiday cottages and find the perfect one waiting for you.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
We have 203 self catering cottages for 4 on the Isle of Wight
3 Windsor House
35482 bedroom self catering apartment near the beach in Ryde.
With spectacular views of the Solent, 3 Windsor House is a neutrally decorated second floor apartment with simple, modern furnishings, just yards from the beach and a short walk in...
Price per week £374 - £795
North View
41252 bedroom self catering cottage with sea views in Seaview.
North View is a wonderful holiday hideaway just on the outskirts of Seaview with sea views across the Solent from the kitchen/dining-room and first floor bedrooms. Set back from th...
Price per week £375 - £825
1 Thatched Cottage
35082 bedroom thatched self catering cottage with sea views in Seaview.
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 property combines old world charm w...
Price per week £379 - £939
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, Spinnakers is situated on a small private estate within walking ...
Price per week £380 - £895
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.
Blakes Barn
39072 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight
If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...
Price per week £380 - £857
Newlands Cottage
36373 bedroom rural self catering cottage near the beach in St Helens, Isle of Wight
Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...
Price per week £383 - £725
8 Appley Sands
35702 bedroom self catering apartment with sea views in Ryde.
8 Appley Sands is a spacious, purpose built, top floor apartment overlooking the Solent and the award-winning beach at Appley. With en suites to both bedrooms, and comfortable, mod...
Price per week £385 - £840
Westbourne Cottage
36943 bedroom, rural self catering cottage near the beach in Seaview, Isle of wight.
Westbourne Cottage is a pretty, pastel-coloured, holiday cottage, located in the picturesque Seagrove Bay. The single level accommodation (ideal for less able guests) is lightly de...
Price per week £390 - £795
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20% off
19 Oct 2018 - 26 Oct 2018
£507.53 £406.02
Gilmerton
36052 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.
Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...
Price per week £392 - £900
Bagwich Barn Cottage
40552 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight
Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...
Price per week £392 - £842
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.