Isle of Wight Holiday Cottages

Setting off on holiday to the Isle of Wight often feels like you’re going on a grand adventure. Sit back and relax on a short ferry crossing and arrive on the Island to a world of nature, gorgeous scenery and plenty of fresh sea air. An Isle of Wight holiday is like no other, and we have a handpicked collection of gorgeous self catering holiday cottages for you to discover…Read more

 There’s plenty for you to do, whether you’re after the picture perfect sunset or an outdoor adventure. We’ve compiled an Isle of Wight Bucket List for you to take your pick of holiday adventures! Why not try something new? There’s kayaking, paragliding, sailing or coasteering for the adventurous, gentle coastal walks and plenty of family friendly attractions. And don't forget the many Isle of Wight festivals!

And as for accommodation, we have dog friendly cottages, cottages with a hot tub, beautiful homes perfect for a family gathering or gorgeous retreats for a romantic getaway. Find your perfect holiday cottage in the Isle of Wight here…

Check out our webcams in Ryde and Freshwater to see what awaits you.  

  

Bembridge beach and RNLI Lifeboat Station at sunrise

165 Luxury self catering cottages on the Isle of Wight

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

7 nights from £840

Daisy Cottage

4824

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


Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located on one of the most desirable locations to live in on the Isle of Wight, ...

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

7 nights from £840

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £600

Temperance

4812

1 bedroom, dog friendly apartment near the beach in Freshwater, Isle of Wight.


Just a few minutes' walk from idyllic Freshwater Bay, Temperance is a real gem. A stylish and spacious first floor apartment, unwind into blissful island life where just a short wa...

  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £600

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

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

7 nights from £1200

The Gate

4813

2 bedroom, dog friendly apartment near the beach in Freshwater, Isle of Wight.


Located a stone's throw from Freshwater Bay, The Gate is a superb newly renovated ground floor apartment by the sea. This simply wonderful retreat has been designed and decorated t...

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

7 nights from £1200

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

7 nights from £1350 *

Hillside

4789

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


A beautifully renovated house tucked away in The Close, just a few minutes from idyllic Seagrove Bay, Hillside is a truly wonderful place to base yourself on the Isle of Wight. Lig...

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

7 nights from £1350 *

View
  • 15% off

    18 Sep 2021 - 25 Sep 2021

    £2499.84 £2125.00

  • 15% off

    25 Sep 2021 - 2 Oct 2021

    £2400.00 £2040.00

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

7 nights from £1100

Old Bembridge House

4791

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


Tucked away on an unmade track just a few yards from the sea and Bembridge Yacht club, this wonderful Classic Cottage has all the makings of a perfect holiday idyll. Laid across th...

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

7 nights from £1100

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

7 nights from £800

The Shack

4730

2 bedroom, dog friendly holiday cottage with sea views in Cowes, Isle of Wight.


The perfect holiday hideaway The Shack, overlooks the waters of the Solent so you can start the day sitting on the front deck with your morning coffee admiring the wonderful view. ...

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

7 nights from £800

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

7 nights from £1680 *

Harbour View

4731

4 bedroom self catering cottage with sea views in Ryde, Isle of Wight.


Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...

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

7 nights from £1680 *

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

7 nights from £725

East View Cottage

4727

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


Nestled at the end of a quiet unmade track, East View Cottage has lovely views across the neighbouring fields and has a large private garden. There is gated access at the front wit...

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

7 nights from £725

Our property managers are local experts who handpick perfect places to stay.

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

7 nights from £800

Starboard Side

4736

2 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.


This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...

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

7 nights from £800

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

7 nights from £1250

Timbuktu

4655

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


Located in Fairy Road in Seaview, Timbuktu is a bright and airy house with plenty of space for a wonderful family holiday on the Island. With a secure gated entrance from the stree...

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

7 nights from £1250

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