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
218 self-catering cottages on the Isle of Wight that sleep 2
4 Tollgate Cottage
41182 bedroom, dog friendly holiday cottage near the beach in Seaview.
4 Tollgate Cottages is located near Seaview on the duver - a beach front area that is home to the stunning Hersey Nature Reserve. This cosy cottage would suit a small family or a c...
Price per week £298 - £730
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20% off
20 Oct 2018 - 27 Oct 2018
£486.62 £389.29
35 Cross Street
35502 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...
Price per week £303 - £680
Faithfull Cottage
36002 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight.
Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...
Price per week £309 - £674
61 Drake Cottage
35652 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
The perfect bolt-hole for families, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview. Just yards from the ...
Price per week £309 - £684
The Lobster Pot
36722 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...
Price per week £312 - £704
6 Sandlands
35612 bedroom, rural self catering apartment near the beach in Ryde.
6 Sandlands is a modest top floor apartment with a large, open plan living area, just a stroll away from Ryde's wonderfully sandy beaches, the canoe lake and the children's sand pa...
Price per week £313 - £660
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.
Hove To
37672 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight
Hove To is one of a small collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked area on two sides with a lovely outlook o...
Price per week £314 - £694
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 new Owner has completely rede...
Price per week £314 - £680
Smugglers’ Run
39452 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight
Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. Watch the boats sail by from the privacy of the balcony off the living-...
Price per week £321 - £648
Sea Thrift
39412 bedroom, rural self catering apartment near Ventnor, Isle of Wight
Situated on the south coast of the Island, Sea Thrift is a pleasant ground floor apartment set in the ground of lovely gardens. With two delightful double bedrooms, both with en su...
Price per week £323 - £653