Cottages for Christmas and New Year 2026 in Isle of Wight

We've found 86 self catering cottages for Christmas and New Year on the Isle of Wight.

Old Bembridge House is a 3 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £908 booking fees included

Old Bembridge House

4791

3 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.


Perfectly located just moments away from the beach and pretty harbour, Old Bembridge House has all the makings of the perfect holiday idyll on the Isle of Wight. Laid across three-...

  • Sleeps 6
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £908

Beggars Roost is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £903 booking fees included

Beggars Roost

4346

3 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...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £903

Longdown Hall is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £882 booking fees included

Longdown Hall

4386

3 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...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £882

Fenders is a 3 bedroom, dog friendly cottage near the beach in Totland.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £869 booking fees included

Fenders

5987

3 bedroom, dog friendly cottage near the beach in Totland.


Your memorable Isle of Wight coastal escape awaits at Fenders, a beautifully appointed single-storey retreat, situated just moments from the picturesque beach at Totland Bay. Tucke...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £869

Wickings is a 3 bedroom, dog friendly holiday cottage near the beach in Ventnor.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £869 booking fees included

Wickings

6101

3 bedroom, dog friendly holiday cottage near the beach in Ventnor.


Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £869

Blackberries is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £867 booking fees included

Blackberries

3583

3 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...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £867

Our guests rate us 4.8/5 on Feefo, the independent review site.

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 £841 booking fees included

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 £841

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 £827 * booking fees included

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 £827 *

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

7 nights from £822 booking fees included

Trevenna

3686

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


Tucked away in a quiet area of Seaview and perfectly situated just a short stroll from the pretty beach and charming village centre, Trevenna is a beautifully furnished, detached h...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £822

48 Solent View is a 3 bedroom self catering cottage with sea views in Seaview.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £808 booking fees included

48 Solent View

5828

3 bedroom self catering cottage with sea views in Seaview.


Just a short wander from the golden sands of Seagrove Bay and the quaint charm of Seaview village, this stylish holiday haven offers modern home comforts in an unbeatable location ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £808

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