May half term holiday cottages

With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover the Isle of Wight

With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to the Isle of Wight. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.

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

We've got 42 holiday cottages matching your search on the Isle of Wight...

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


This charming first floor apartment is laid over two floors and situated right in the heart of Seaview village, tucked away down a quiet side street called Rope Walk, so called as ...

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

Price per week £810

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  • 10% off

    12 May 2018 - 19 May 2018

    £509.96 £459.00

  • 10% off

    19 May 2018 - 26 May 2018

    £509.96 £459.00

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

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

Price per week £950

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

3 bedroom self catering apartment with sea views in Seaview.


They say location is everything, and this property does not disappoint! Situated on the first floor, 2 Quay Rocks is a light-filled, modestly furnished apartment with a balcony, of...

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

Price per week £795

3 bedroom self catering cottage near the beach in Seaview.


This modern, well-presented town house is located in a small development in the centre of Seaview. A true home-from-home, 2 Sandpipers is perfect for a coastal break with the famil...

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

Price per week £810

3 bedroom self catering cottage in East Cowes, Isle of Wight


Turnstone is a beautifully designed, newly built town house situated overlooking the River Medina on the north coast of the island and within walking distance of Osborne House. Fro...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £825

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


Nestled in the heart of Seaview village this lovely ground floor apartment is a stone’s throw from the sea front and all the village amenities. Seaview is an idyllic Edwardian reso...

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

Price per week £850

3 bedroom self catering cottage in Whitwell, Isle of Wight


Set in the rural village of Whitwell less than three miles outside of Ventnor, Willow Tree Lodge is a semi-detached bungalow offering comfort inside and out. Inside there are delig...

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

Price per week £997

3 bedroom self catering cottage with sea views in Ryde, Isle of Wight


This absolutely stunning property is laid over five mezzanine floors, has two sea-facing balconies and a hot tub with a sea view! Beautifully decorated throughout, The Lodge offers...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £1295

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

3 bedroom, dog friendly holiday cottage near the beach in Totland, Isle of Wight


Ashmead Cottage has been thoughtfully decorated throughout offering three lovely bedrooms and two modern bathrooms. The kitchen opens out onto a charming private decked-area with o...

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

Price per week £863

4 bedroom self catering apartment near the beach in Seaview.


Crowsteps is on the first and second floor of a property tucked away in Seaview in a semi detached property. Boasting a stunning roof terrace with far reaching views over the Solen...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £1121

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