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
213 self-catering cottages on the Isle of Wight that sleep 2
Spring Tide
36602 bedroom self catering cottage at Island Harbour, near Newport.
Spring Tide is a delightful holiday cottage situated in a small development at Island Harbour Marina on the banks of the River Medina. The marina is set in a beautiful secluded val...
Price per week £351 - £806
4a Ship House
35563 bedroom self catering cottage near the beach in Seaview, Isle of Wight
4A Ship House, an attractive townhouse positioned right in the middle of Seaview, is perfect for a family looking for a coastal break. 'Ship shape' in presentation, the fantastic t...
Price per week £357 - £810
Don’t miss out; reserve your favourite 2019 holiday cottage for just £30
Reserve your 2019 holiday
Our portfolio gets better year after year, with all the old favourites and some stunning new additions, so get in there quick and reserve your preferred dates for only £30.
Pick a place close to the coast for that year-round holiday vibe, or book a holiday townhouse to be close to every convenience. Escape to the country for peace and quiet or take to the moors for walks through wide open spaces, we’ve got plenty of holiday cottages for you to choose from for next year.
Reserve next year's holiday in advance to give you peace of mind and put off paying your deposit till after this summer (5th October). That way you know your preferred dates are yours for the choosing and you can get on with enjoying the rest of this year's holiday (before looking forward to the next!).
Starfish
39522 bedroom self catering apartment near the beach in Ventnor, Isle of Wight
Accessed via a set of stairs, this bright and airy first and second floor apartment offers contemporary accommodation, with large and spacious rooms packed with period features, hi...
Price per week £384 - £760
Elm Cottage
35973 bedroom self catering apartment with sea views in Seaview, Isle of wight.
Elm Cottage is a stylish, spacious first floor apartment, brimming with quirky taste and character, in the sought after village of Seaview and it enjoys sea views across the roof t...
Price per week £396 - £895
40 Trelawny Way
35553 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...
Price per week £405 - £1071
2 Sea Whispers
39783 bedroom self catering cottage near the beach in Seaview, Isle of Wight
This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...
Price per week £405 - £950
September Cottage
36553 bedroom self catering cottage near the beach in Brook.
September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...
Price per week £413 - £898
Old Coastguards
36402 bedroom, dog friendly holiday cottage near the beach in Alum Bay, Isle of Wight.
Where to start in describing Old Coastguards? Our highlights are the tremendous views, log burning sauna with external heated shower, and roll-top bath, not to mention luxurious fu...
Price per week £460 - £1030
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Manor Farm Cottage
41623 bedroom, dog friendly self catering cottage in Ventnor.
This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...
Price per week £481 - £1050
Chillerton Farm Barn
39643 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight
This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...
Price per week £495 - £1050