Isle of Wight Cottages for February Half-Term

Isle of Wight Cottages for February Half-Term

An island paradise for February half term, how does that sound? Escape to the Isle of Wight and stay in a holiday cottage for a week or a long weekend, or even a fortnight! You might as well make the most of the ferry trip and stay for as long as work/school allows. There's plenty to explore on this seaside holiday destination mecca, while breathing in the sea air and taking in the views, all a million miles away from the everyday on the mainland. Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

65 handpicked cottages available for February half-term on the Isle of Wight

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 £851 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 £851

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

7 nights from £951 booking fees included

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space for modern living. Situated o...

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

7 nights from £951

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

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 £961 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 £961

Sun Lodge is a 4 bedroom, dog friendly holiday cottage with sea views in Ventnor.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1098 booking fees included

Sun Lodge

5853

4 bedroom, dog friendly holiday cottage with sea views in Ventnor.


Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1098

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Pucks Oak is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1151 booking fees included

Pucks Oak

5698

4 bedroom, dog friendly holiday cottage with sea views in Seaview.


Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1151

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £769 booking fees included

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £769

The Dairy is a 3 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1064 booking fees included

The Dairy

5631

3 bedroom self catering cottage near the beach in Seaview.


Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...

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

7 nights from £1064

Tangle Cottage is a 4 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £791 * booking fees included

Tangle Cottage

5669

4 bedroom self catering cottage near the beach in Seaview.


Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £791 *

Inglefield is a 4 bedroom, dog friendly holiday cottage near the beach in St Helens.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £971 booking fees included

Inglefield

5637

4 bedroom, dog friendly holiday cottage near the beach in St Helens.


This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £971

Colwell Bay Cottages

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1553.96 booking fees included

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Traditional seaside holiday dreams will come true on an Isle of Wight half term holiday. It's a beautiful island, where people would come to convalesce, and you can see why; the views, the atmosphere, the pace of life. It's truly relaxing. But don't be fooled there's plenty of entertainment and things to do on the Isle of Wight during Feb half term.

Little ones (and not-so-little ones) will delight in the variety of attractions available, from Blackgang Chine to Osborne House, to a simple walk to take in the landscape, coupled with your perfect place to stay - you'll have a great time. Many of our cottages include games rooms, swimming pools, enclosed gardens and great locations near to coastal paths and beaches - great news for your four-legged friend, if you pick a dog-friendly cottage on the island.

February Half-Term Cottages on the Isle of Wight 

Treat yourselves to the holiday of a lifetime and book a break in a self-catering cottage. We've handpicked cottages we want to stay in ourselves, so you'll want for nothing when you stay. All of our cottages have been personally inspected and totally equipped with everything you could need and more - even down to checking the teaspoons so as soon as you arrive at your Isle of Wight holiday cottage, you can pop the kettle on, your feet up and relax.