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
The Battenburg Studio
36641 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...
Price per week £240 - £620
The Beatrice Studio
36661 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.
Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...
Price per week £240 - £620
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The Sail Loft
41071 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous top floor one bedroom apartment has spectacular sea views over the rooftops across the Solent and is just a few minutes from Seaview village and the beach. Newly dec...
Price per week £250 - £500
Little Barn Retreat
41871 bedroom, rural self catering cottage in Newport, Isle of Wight
This absolutely gorgeous barn conversion is the perfect place for a couple's holiday, located on the Durton Farm Estate in the centre of the Island. Lovingly refurbished by the own...
Price per week £250 - £500
Grace Cottage
42091 bedroom, dog friendly cottage near 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. Laid over on...
Price per week £250 - £500
West Flatlet
36921 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...
Price per week £252 - £429
Sea Song
39401 bedroom self catering apartment near Ventnor, Isle of Wight
Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...
Price per week £265 - £485
Mariners Cove
36281 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy the ev...
Price per week £266 - £460
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.
Berryl Mead View
39061 bedroom self catering cottage near Ventnor, Isle of Wight
Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room wit...
Price per week £275 - £536
The Ivy
36711 bedroom, dog friendly holiday apartment near the beach in Shanklin, Isle of Wight.
The Ivy is a compact double bedroom annexe offering comfortable accommodation for a couple seeking a relaxing island escape. Ideally located, with Shanklin village and beach a shor...
Price per week £295 - £510