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.
Our exclusive ferry discounts will make your island trip with Classic plain sailing.
136 self-catering cottages on the Isle of Wight that sleep 2
7 nights from £1187 *
Solas
44594 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
This superb, spacious detached house close to Seaview village has wonderful sea views from the first floor open plan sitting/dining-room and balcony. Taking full advantage of the v...
7 nights from £1187 *
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30% off
21 Dec 2024 - 28 Dec 2024
£2492.00 £1744.40
7 nights from £1251 *
Saye House
45734 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...
7 nights from £1251 *
7 nights from £1285 *
Newclose Houseboat
52004 bedroom houseboat with sea views in Bembridge, Isle of Wight
Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...
7 nights from £1285 *
7 nights from £1353 *
Windy Ridge
44644 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...
7 nights from £1353 *
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £1469 *
Pepita
57195 bedroom dog friendly cottage with sea views in Seaview.
With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...
7 nights from £1469 *
7 nights from £650
The Little Dairy Park Farm
56362 bedroom, dog friendly holiday cottage near Ryde, Isle of Wight.
This welcoming retreat is close to the pretty village of Seaview and the sandy beach at Ryde, and has the Isle of Wight Gin Distillery within walking distance. Thoughtfully present...
7 nights from £650
7 nights from £654
7 Sandpipers
35683 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...
7 nights from £654
7 nights from £767
Sunnyside
49603 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, Sunnyside is an appealing dog friendly holiday abode fully refurbished in 2021/22. It is set in...
7 nights from £767
7 nights from £834
10 Shanklin Manor
35113 bedroom, apartment with roof terrace near the beach in Shanklin, Isle of Wight.
This superb two-storey, first floor apartment dating back to 1863 is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the use of a la...
7 nights from £834
7 nights from £845
Limpets
46223 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...
7 nights from £845
Choose from our exclusive collection at the best prices with real time availability.
Exclusive cottage collections
Our calendars show live availability, so if your pick of dates are available, you can reserve them safe in the knowledge that they won’t get sold anywhere else.
It can be unpredictable using aggregator websites that collect up information from across multiple websites. Our website stands alone, so you know what to expect and what you will get, for the best price. You won’t find this collection of cottages anywhere else, so pick your perfect place to stay from our exclusive portfolio.
