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

175 Luxury self catering cottages on the Isle of Wight

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

7 nights from £385

The Worsley Apartment

3682

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 within Shanklin Villa, a beautifully converted Victorian building. With a separate kitc...

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

7 nights from £385

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

7 nights from £479

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone.


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 £479

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

The Beach Retreat

3665

2 bedroom self catering cottage near the beach in Seaview.


This delightful compact seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, o...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £290

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

7 nights from £316

61 Drake Cottage

3565

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


The perfect bolthole for families in a quiet corner away from the road, 61 Drake Cottage is a comfortably furnished beach bungalow located in a small waterside development on the e...

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

7 nights from £316

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

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

7 nights from £319

The Lobster Pot

3672

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

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

7 nights from £319

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

7 nights from £328

Hove To

3767

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


Hove To is one of a collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked-area on two sides with a lovely outlook over th...

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

7 nights from £328

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

7 nights from £328

Cockleshells

3815

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The accommodation is compact with...

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

7 nights from £328

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

7 nights from £334

Smugglers’ Run

3945

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


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. It would suit a family or a couple in need of a little extra space. ...

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

7 nights from £334

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

7 nights from £343

Faithfull Cottage

3600

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


Faithfull Cottage is a lovingly restored, pretty mid-terrace cottage which enjoys a rear garden and countryside views on the outskirts of St Helens. This comfortable cottage is set...

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

7 nights from £343

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

7 nights from £357

6 Pier View Court

3559

2 bedroom self catering apartment near the beach in Ryde.


6 Pier View Court, perfectly located right on the seafront at Ryde, is a modern, well presented second floor apartment, tastefully decorated and furnished to a high standard. Relax...

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

7 nights from £357

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

Loading more