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. Snap up your 2021 holiday for just £30 this October and we will hold your reservation for you until the 1st December. Read more
Reserve your 2021 holiday for £30 - How it works
Choose your favourite cottage and preferred 2021 holiday dates and complete the reservation form. We will then email you with a reservation confirmation and invite you to take up our £30 reservation offer. All that's left to do is opt in via email and you're set! The full deposit will then be due on the 1 December 2020. And don't worry, there's no catch. This offer simply allows us to extend your reservation until 1 December for you. Please see our blog for further details.
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 book 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 124 Self catering holiday cottages for rent in 2021
7 nights from £900
Culver View
45554 bedroom self catering cottage near the beach in St Helens, Isle of Wight.
Located down a single-track road off the lower Green in the village of St Helens, Culver View has a beautiful garden and far reaching views over Culver Downs. A spacious and light ...
7 nights from £900
7 nights from £1600
Redworth
45415 bedroom self catering home near the beach in Bembridge, Isle of Wight.
This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk to the lo...
7 nights from £1600
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 £540
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle eof Wight.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £540
Kingston Barns
7 nights from £2170
7 nights from £540
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...
7 nights from £540
7 nights from £595
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...
7 nights from £595
7 nights from £495
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...
7 nights from £495
7 nights from £1250
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 living/dining-room and balcony. Taking full advantage of the vi...
7 nights from £1250
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10% off
24 Oct 2020 - 24 Oct 2020
£1900.08 £1710.07
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7 nights from £2100
Little Forelands
44745 bedroom self catering cottage with sea views in Bembridge, Isle of Wight
This absolutely lovely family home in Bembridge, on the east coast of the Isle of Wight, has a large garden and stunning sea views. With a gated entrance Little Forelands is ideall...
7 nights from £2100
7 nights from £409
Spindrift
44372 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This gorgeous two bedroom terraced cottage is a few minutes from the beach, right in the heart of Seaview village, offering an ideal holiday bolthole on the picturesque Isle of Wig...
7 nights from £409