Isle of Wight Cottages Sleeping 2
Whether you’re looking for a romantic break in a cosy cottage or a chance to rest and recharge with a family member, there’s a cottage that sleeps two for every visit on the Isle of Wight. With each property handpicked and carefully inspected, we pride ourselves on offering the finest quality self-catering accommodation with excellent customer service. Book with confidence with Classic Cottages.
Staying in a cottage for two gives you enough space to relax and unwind without being too big. Plan a getaway to the island and enjoy the broad diversity that it has to offer. Plan a romantic break together for a special occasion or take a trip with a family member for some quality time together.
As soon as you cross the Solent, you’ll feel all your worries melt away. This is where your holiday begins. Spend the journey nestled together discussing your plans and what you’d like to see the most before heading back to your car to drive on to the isle.
For walkers, the hills of West Wight make an excellent playground for two. Mix the coast paths with walks further inland around Freshwater Bay or Brighstone to really see the nature of the island. If you prefer a classic promenade with golden sands, waltz along the coast at Sandown, Shanklin and Ventnor. These classic Victorian holiday locations still have their historic charm. Shanklin Old Town is particularly picturesque with thatched roofs and souvenir shops. There’s also amazing opportunities for cycling: there are several cycling festivals throughout the year and plenty of routes for all abilities across the island.
Finding foodie hotspots isn’t hard here. Newport plays host to some excellent restaurants. Thompson’s offers a classic dining experience with an amazing display of culinary expertise. For taste with a twist, we love Nomad. A cool restaurant with a focus on Mexican and Asian fusion. They bring your food out on tiles and have a set menu called ‘Shut and feed me’. What more is there to love? For daytime dining, Ventnor and Godshill in the South have a host of individual cafes to pop in for a cup of tea whilst exploring the island. Whilst in Ventnor, stop by the beautiful botanical gardens to take some lovely photographs with your travel buddy and enjoy the tranquillity of this part of the isle.
No matter the time of year, a lovely cottage for two will make a beautiful bolthole for couples, a homely hub for friends and the perfect base for family visiting the island together.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
180 self-catering cottages on the Isle of Wight that sleep 2
7 nights from £435
2 Sandpipers
35253 bedroom self catering cottage near the beach in Seaview.
This modern, well-presented townhouse situated in a small development in the centre of Seaview would suit a family, a couple or several friends traveling together. It really is...
7 nights from £435
7 nights from £435
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...
7 nights from £435
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 £444
Trafalgar
40573 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Nestled in the heart of Seaview village, this lovely ground floor apartment is a stone's throw from both the coastline and village amenities, in fact it is just steps away from a f...
7 nights from £444
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10% off
29 Mar 2019 - 5 Apr 2019
£510.00 £459.00
7 nights from £445
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...
7 nights from £445
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10% off
30 Mar 2019 - 6 Apr 2019
£502.81 £452.53
7 nights from £462
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
A hidden gem tucked away on Bluett Avenue in the peaceful Victorian village of Seaview, Lawn End makes great use of accent colours in its interior decor presenting a beautiful holi...
7 nights from £462
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10% off
29 Mar 2019 - 5 Apr 2019
£530.61 £477.55
7 nights from £470
4 Commodores Court
35533 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The wow factor at 4 Commodores Court is the location; perched directly opposite the beach, it offers stunning views of The Solent to the front, and delightful rural and lakeside vi...
7 nights from £470
7 nights from £479
6 Coastguard Cottages
35583 bedroom, dog friendly holiday cottage near the beach in Brook, Isle of Wight.
Formerly the officer's quarters of the coastguard station, 6 Coastguard Cottages has been beautifully decorated and offers a wonderful holiday home in Brook. This period property h...
7 nights from £479
7 nights from £480
3 Springfield Court
35473 bedroom self catering apartment near the beach in Seaview.
With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...
7 nights from £480
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 £480
Merries
36293 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Merries is a traditional beachside bungalow conveniently situated between Puckpool Park and Seaview village centre. It would suit a family wanting a convenient coastal holiday base...
7 nights from £480
7 nights from £480
The Barn
36633 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.
The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...
7 nights from £480
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15% off
30 Mar 2019 - 6 Apr 2019
£565.02 £480.27