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, SussexIsle 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. 

Isle of Wight Ferry Booking 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

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

Culver View

4555

4 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 ...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £900

  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1600

Redworth

4541

5 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...

  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1600

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £540

The Stables

4537

2 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 ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £540

Kingston Barns

  • Sleeps 15 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £2170

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £540

The Pigsty

4538

2 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...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £540

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £595

The Dairy

4536

2 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...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £595

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £495

The Cattle Byre

4535

2 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...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £495

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1250

Solas

4459

4 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...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1250

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  • 10% off

    24 Oct 2020 - 24 Oct 2020

    £1900.08 £1710.07

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  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £2100

Little Forelands

4474

5 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...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £2100

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £409

Spindrift

4437

2 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...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £409

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