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 69 holiday cottages matching your search on the Isle of Wight...

1 bedroom self catering apartment near Ventnor, Isle of Wight


Sea Song is an attractive one bedroom, first floor apartment in the heart of beautiful communal gardens and woodlands. Perfect for romantic getaways as it is set in a rural locatio...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

Price per week £408

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


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...

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

Price per week £435

1 bedroom, rural self catering cottage near Newport, Isle of Wight


Little Tremore Cottage is a charming annexe situated in the historic village of Shorwell, surrounded by peaceful and idyllic countryside; this is the place to be for a romantic, re...

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

Price per week £465

2 bedroom self catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space, well equipped throughout and extremely comfortable living room. Ma...

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

Price per week £470

1 bedroom, dog friendly holiday apartment near the beach in Shanklin, Isle of Wight.


The Ivy is a compact double bedroom annexe offering comfortable accommodation for a couple seeking a relaxing island escape. Ideally located, with Shanklin village and beach a shor...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £478

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


Sitting within a beautifully converted Victorian villa, The Cadogan Apartment offers a high standard of accommodation for a couple or lone traveller looking for a coastal break. Gu...

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

Price per week £660

2 bedroom self catering cottage near the beach in Seaview.


Located in a small waterside development on the edge of Seaview, 62 Buddleia Cottage is a pretty beach bungalow offering comfortable accommodation for a couple or small family in a...

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

Price per week £572

2 bedroom, rural self catering apartment near Ventnor, Isle of Wight


Situated on the south coast of the Island, Sea Thrift is a pleasant ground floor apartment set in the ground of lovely gardens. With two delightful double bedrooms, both with en su...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

Price per week £528

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural location. Located...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £550

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

Price per week £560

Loading more