Holiday cottages for 2021 in Isle of Wight
Ready to start planning your 2021 adventure? Now's a great time to get ahead of the crowd.Read more
Head to Cornwall, Devon, Somerset, Dorset, Sussex, Isle of Wight, Pembrokeshire or Kent with Classic in 2021. We have a portfolio of properties ready and waiting for you to start planning your next self catering holiday. Why not now and then relax later, knowing you've got your holiday for next year sorted.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
We have 79 Self catering holiday cottages for rent in 2021
7 nights from £563
2 Shanklin Manor
43492 bedroom self catering apartment near the beach in Shanklin, Isle of Wight
A large and impressive building, Shanklin Manor is on the outskirts of Shanklin Old Village and within easy reach of all the amenities and the beach, making it a fabulous holiday d...
7 nights from £563
7 nights from £715
The Shute
43993 bedroom dog-friendly self catering cottage with sea views near Ventnor, Isle of Wight.
This gorgeous cottage, set in the breathtaking location of St Lawrence, has a large patio and unrivalled sea views. A truly magical place to sit and enjoy the scenery, the seaward ...
7 nights from £715
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.
7 nights from £461
Upton View
43502 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Upton View is a lovely cottage on the outskirts of Seaview with double doors opening out from the dining-area to a gorgeous garden and, with outdoor seating, you can while away you...
7 nights from £461
7 nights from £613
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £613
7 nights from £815
Sunset Cottage
43193 bedroom self catering cottage near Ventnor, Isle of Wight
Set in the grounds of the impressive Pyle Manor, this newly refurbished cottage offers a wonderful base on the Isle of Wight with the shared use of an outdoor unheated swimming poo...
7 nights from £815
7 nights from £429
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 £429
7 nights from £1800
Belgrove House
42435 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
This is an absolutely stunning detached house situated along Ducie Avenue, a private unmade road leading to the beach, in the charming seaside village of Bembridge. Within a few mi...
7 nights from £1800
7 nights from £621
House of Logs
42254 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...
7 nights from £621
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 £722
Oak Tree Cottage
42123 bedroom self catering cottage with sea views in Seaview, Isle of Wight
With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...
7 nights from £722
7 nights from £893
Glebe House
42105 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight
This is a three-storey house right in the heart of Bembridge village, just opposite the picturesque village church and a few minutes' walk from the shops and restaurants. The prope...
7 nights from £893