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 £550
Pandora Lodge
36423 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...
7 nights from £550
7 nights from £551
Lanthorn Cottage
42873 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight
Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...
7 nights from £551
7 nights from £565
East Gull Sands
35953 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...
7 nights from £565
7 nights from £599
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...
7 nights from £599
7 nights from £600
Lawn End
36173 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Tucked away in a quiet corner of the delightful village of Seaview, Lawn end is a quirky island retreat, tastefully furnished to offer contemporary living for families or a group o...
7 nights from £600
7 nights from £691
Trevenna
36863 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or couples travelling tog...
7 nights from £691
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.
7 nights from £715
Modwena
44683 bedroom self catering cottage near the sea in Yarmouth, Isle of Wight.
This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk from the village centre and historic pier. Located on the west coast of the Isla...
7 nights from £715
7 nights from £725
3 Springfield Court
35473 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
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 £725
7 nights from £739
Blackberries
35833 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
A warm Isle of Wight welcome awaits you at Blackberries, a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike, in the delightful sail...
7 nights from £739
7 nights from £775
Beggars Roost
43463 bedroom self catering apartment with sea views in Seaview, Isle of Wight
This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...
7 nights from £775
