Holiday Cottages for October on the Isle of Wight

101 self-catering cottages on the Isle of Wight

Sheldonia is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £791 *

Sheldonia

5109

3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.


Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...

  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £791 *

Sugar Beach is a 2 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £445

Sugar Beach

5102

2 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight


Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...

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

7 nights from £445

Underwood Cabin is a 3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £775 *

Underwood Cabin

4995

3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.


Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £775 *

18 Seaview Bay is a 1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £665

18 Seaview Bay

4996

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming, sunny apartment found in a small development, close to the villag...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £665

Sea Lights is a 2 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1034 *

Sea Lights

4967

2 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet-friendly apartment...

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

7 nights from £1034 *

Oceanix is a 1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £646

Oceanix

4900

1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.


A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect seaside getaway for your next Isle of Wight holiday. The property has been though...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £646

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £625 *

Valdora

4959

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £625 *

Oystercatcher is a 3 bedroom luxury houseboat in Bembridge, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1229 *

Oystercatcher

4869

3 bedroom luxury houseboat in Bembridge, Isle of Wight.


Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1229 *

View
  • 10% off

    11 Jul 2025 - 18 Jul 2025

    From £2064.00 £1857.60

Westhill View is a 2 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £510

Westhill View

4882

2 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.


With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £510

9 The Ruskins  is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1053 *

9 The Ruskins

4865

3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.


This delightful family holiday home can be found just a short stroll from the beautiful beaches of Bembridge and a wonderful array of traditional shops and restaurants. Light fille...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1053 *

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