Isle of Wight short breaks

The Isle of Wight is perfect for that weekend break or much-needed mid-week breather. The diversity of the island’s environments means you can find lush countryside, dramatic coastal scenes and gorgeous yacht harbours all in one place. If you want a sneaky peak of the Isle of Wight check out our new webcams.Read more

Fall in love with island life and enjoy a cosy rural retreat or a seaside escape in our luxury self-catering cottages. The isle is a perfect little getaway, only four hours from central London by car and you can be in a gorgeous holiday cottage ready to relax for a dreamy short break. Choose from an array of beautiful baby friendly and dog friendly holiday lets to cater for the whole family.

 

Spring and Autumn Breaks on the Isle of Wight

The mild climate of the isle creates beautiful Spring and Autumn landscapes to enjoy as summer crowds fade away. Spend three to four days surrounded by peaceful forests and serene seascapes away from the hustle and bustle.

 

Summer Short Breaks

Enjoy yachts, festivals, blue skies and sea breezes with a Summer on the Isle of Wight. With the island playing host to the Isle of Wight festival, Bestival and Cowes Week to name but a few, there are plenty of things to do in the Summer here. A short break in a holiday cottage is the ideal way to enjoy these festivals in style, without having to deal with the mud or rain.

 

Christmas on the Isle of Wight

Create magical Christmas memories with a holiday away from the mainland to really relax into the festive season. Book a short break on the Isle of Wight to discover an enchanted island filled with beautiful cottages to make your break one to remember. You may even be treated to a touch of snow.

 

New Year Breaks on the Isle of Wight

With celebrations taking place all over the Isle of Wight, you’re in for an amazing New Year celebration if you choose to go island-style. Close-knit communities means that everyone comes together. Have a memorable time dancing the night away with friends old and new.

 

Winter Breaks on the Isle of Wight

The island has a warmer climate than the mainland making winters less harsh. Ventnor supposedly benefits from the most daylight hours and the mildest climate in the UK. Although we can’t promise a tropical winter, there’s a good chance that the sun may shine for your winter holiday on the Isle of Wight. For added cosy, choose a holiday cottage with a fire on the Isle of Wight and spend your evenings curled up with a hot chocolate or a mulled wine warming your toes.

 

We have 114 holiday cottages available on the Isle of Wight for you to enjoy some well-deserved time off.

We have 114 self-catering cottages on the Isle of Wight available for a Short Break

  • 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

    19 Jul 2021 - 24 Jul 2021

    £2660.40 £2261.34

  • 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

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

  • 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 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

  • 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 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £1200

The Tap Room

4699

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


If you are looking to holiday in a place that is just that little bit special then The Tap Room at Golden Hill Fort is for you. New to the Classic Cottage portfolio, the panoramic ...

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

7 nights from £1200

  • 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

  • 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

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • 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

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