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

166 Luxury self catering cottages on the Isle of Wight

  • 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

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £850

The Tap Room

4699

3 bedroom luxury apartment near the beach in Freshwater, Isle of Wight.


If you are looking for that very special holiday in a truly unique location, then The Tap Room at Golden Hill Fort is for you. New to the Classic Cottage portfolio in 2021 the pano...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £850

View
  • 25% off

    30 Oct 2021 - 5 Nov 2021

    £1550.00 £1162.50

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £2000

Elmscott

4664

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


This gorgeous family home, within a few minutes' walk to Yarmouth town centre, has not only lovely accommodation but an outdoor heated pool set in a stunning garden. With off stree...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £2000

View
  • 10% off

    22 Oct 2021 - 29 Oct 2021

    £2649.92 £2385.00

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

7 nights from £300

1 Harrow Cottages

4642

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


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

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

7 nights from £300

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

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £850

Benhams

4578

4 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.


Located within walking distance of Freshwater Bay, stopping en route at the charming Piano Cafe for a spot of lunch or coffee and home-made cake, Benhams is an ideal base. The brea...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £850

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1950 *

St Andrews

4641

6 bedroom, dog friendly holiday home near the beach in Yarmouth, Isle of Wight.


Wow! This spectacular converted church has the makings for the most amazing holiday, set in an elevated position with panoramic views across the surrounding countryside and a glimp...

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1950 *

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £675

Limpets

4622

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


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £675

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

7 nights from £700

Pinings Yard

4625

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


This gorgeous, tucked away cottage is just a short stroll from the centre of Yarmouth and a real delight. Gated access off a narrow unmade track, leading to the sea, takes you to y...

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

7 nights from £700

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1500 *

Woodlands

4594

6 bedroom self catering home with sea views in Seaview, Isle of Wight.


This simply stunning four-storey, six bedroom house is situated in the village of Seaview within a few minutes' walk to the beach. With sea views from the top floor bedroom, Woodla...

  • Sleeps 12 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1500 *

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1000

1 Church House

4596

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


A simply stunning church conversion in Totland on the west coast of the Island and within walking distance to the beach, making this the perfect holiday destination. Beautifully co...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1000

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

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