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.
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...
2 Sea Whispers
39783 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 ...
Price per week £810
Chillerton Farm Barn
39643 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...
Price per week £950
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
2 Quay Rocks
35243 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...
Price per week £795
2 Sandpipers
35253 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...
Price per week £810
Turnstone
38283 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...
Price per week £825
Trafalgar
40573 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...
Price per week £850
Willow Tree Lodge
39493 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...
Price per week £997
The Lodge
40093 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...
Price per week £1295
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Ashmead Cottage
37233 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...
Price per week £863
Crowsteps
37364 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...
Price per week £1121