Isle of Wight Holiday Cottages

Our exclusive Isle of Wight cottages are handpicked and inspected by our team of local island experts. From dog friendly homes with enclosed gardens to luxury cottages with a hot tub, we’ve selected properties with great holidays in mind. With some of the best coast and countryside in Britain, the Isle of Wight is perfect for a romantic break for two or a family gathering with pets and all. Check out our webcams in Ryde and Freshwater to see what awaits you.Read more

About the Isle of Wight

Small but mighty, this 23 by 13 mile island is a hidden gem of escapism in the United Kingdom. The size of the island makes it easy to get around once you’re here and the proximity to the mainland makes it even easier to get here in the first place. Around 3 hours from London, the Isle of Wight is perfect for a weekend getaway in a luxury cottage if you’re looking for a relaxing short break. 

We know this island like no one else, and if you’re after some local tips we’ve got plenty, as we document the best things to do on the Isle of Wight on our blog. From top sunset spots to Christmas markets, we’ve found some real island gems for your visit. Whether you’re after a hive of activity or something more off the beaten track, take a look at our blog or speak to our Isle of Wight team for some hints from the experts.

  

Holiday cottages on the Isle of Wight The Needles on the western tip of the IOW

 

Where to stay on the island

To make your holiday special, we've picked out a great selection of self catered homes across the island for whatever you need. If you're getting the family together and need a place fit for a big group, we have plenty of large family friendly Isle of Wight cottages to accommodate you all. Or for a more romantic feel, tuck yourself away in one of our cottages for two away from it all on the island.

This is a great destination for holidays with pets too, with plenty of dog friendly beaches and pubs welcoming dogs all year round. Most importantly, we’ve got plenty of dog friendly cottages on the Isle of Wight just waiting to welcome you and your furry friend.

  

The rolling country side with sea views on the Isle of Wight Modern holiday home on the isle of wight

 

Add a little luxury

Our Isle of Wight holiday cottages with a pool might be just what you need, and many properties come equipped with a private hot tub as well. Sink back and embrace the relaxing island lifestyle in a luxury holiday cottage – you’ve earned it.

For an even more relaxing break look no further than a holiday cottage near the beach, with a sunbathe or a sea swim only steps away. Wherever you stay on the Isle of Wight you won’t be too far from the sea but if it’s sandcastles and surfboards on your mind, choosing one of our self catering spots near the beach is a must.

 

Bembridge beach and RNLI Lifeboat Station at sunrise

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

218 Luxury self catering cottages on the Isle of Wight

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

7 nights from £335

1 bedroom, dog friendly cottage near the beach near Old Freshwater, Isle of Wight.


If a quintessentially English cottage is what you're after for your holiday, look no further than Afton Lodge. Set in Old Freshwater, the lodge boasts a thatched roof, stable door ...

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

7 nights from £335

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

View
  • 20% off

    20 Dec 2018 - 27 Dec 2018

    £659.97 £528.00

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £309

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation, for a couple or small family, in...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £309

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Offering a high standard of accommodation, the Worsley Apartment is a ground floor apartment housed within Shanklin Villa, a beautifully converted Victorian building. With a separa...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £360

We’ve been raising the standards of self catering holidays since 1977.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £251

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


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £251

View
  • 20% off

    14 Dec 2018 - 21 Dec 2018

    £313.54 £251.20

  • 20% off

    24 Dec 2018 - 28 Dec 2018

    £596.00 £476.80

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

2 bedroom self catering cottage near the beach in Seaview.


This stylish, compact seaside bungalow is located in a front row position with wonderful views across the Solent. It would ideally suit a family with young children or a couple loo...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

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

7 nights from £295

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


Take a few steps up to the entrance and you will find yourself in 3 Kings House, a ground floor apartment in a small development. It is the perfect base for a couple or a family wi...

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

7 nights from £295

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

7 nights from £295

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


This two bedroom apartment in Bembridge is small but perfectly formed. Lovingly restored by the owners, 53a offers a perfect base for a family with a light and airy double bedroom ...

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

7 nights from £295

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

7 nights from £295

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


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

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

7 nights from £295

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

7 nights from £303

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


35 Cross Street is a cute end of terrace townhouse with accommodation spread over three floors, and has a sunny, enclosed courtyard. Built at the turn of the century, and decorated...

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

7 nights from £303

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

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