Isle of Wight Holiday Cottages
Setting off on holiday to the Isle of Wight often feels like you’re going on a grand adventure. Sit back and relax on a short ferry crossing and arrive on the Island to a world of nature, gorgeous scenery and plenty of fresh sea air. An Isle of Wight holiday is like no other, and we have a handpicked collection of gorgeous self catering holiday cottages for you to discover…Read more
There’s plenty for you to do, whether you’re after the picture perfect sunset or an outdoor adventure. We’ve compiled an Isle of Wight Bucket List for you to take your pick of holiday adventures! Why not try something new? There’s kayaking, paragliding, sailing or coasteering for the adventurous, gentle coastal walks and plenty of family friendly attractions. And don't forget the many Isle of Wight festivals!
And as for accommodation, we have dog friendly cottages, cottages with a hot tub, beautiful homes perfect for a family gathering or gorgeous retreats for a romantic getaway. Find your perfect holiday cottage in the Isle of Wight here…
Check out our webcams in Ryde and Freshwater to see what awaits you.
166 Luxury self catering cottages on the Isle of Wight
7 nights from £1250
Timbuktu
46554 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Located in Fairy Road in Seaview, Timbuktu is a bright and airy house with plenty of space for a wonderful family holiday on the Island. With a secure gated entrance from the stree...
7 nights from £1250
7 nights from £850
The Tap Room
46993 bedroom luxury apartment near the beach in Freshwater, Isle of Wight.
If you are looking for that very special holiday in a truly unique location, then The Tap Room at Golden Hill Fort is for you. New to the Classic Cottage portfolio in 2021 the pano...
7 nights from £850
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25% off
30 Oct 2021 - 5 Nov 2021
£1550.00 £1162.50
7 nights from £2000
Elmscott
46643 bedroom self catering cottage near the beach in Yarmouth, Isle of Wight.
This gorgeous family home, within a few minutes' walk to Yarmouth town centre, has not only lovely accommodation but an outdoor heated pool set in a stunning garden. With off stree...
7 nights from £2000
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10% off
22 Oct 2021 - 29 Oct 2021
£2649.92 £2385.00
7 nights from £300
1 Harrow Cottages
46421 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...
7 nights from £300
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £850
Benhams
45784 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...
7 nights from £850
7 nights from £1950 *
St Andrews
46416 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...
7 nights from £1950 *
7 nights from £675
Limpets
46223 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 ...
7 nights from £675
7 nights from £700
Pinings Yard
46252 bedroom self catering cottage near the beach in Yarmouth, Isle of Wight.
This gorgeous, tucked away cottage is just a short stroll from the centre of Yarmouth and a real delight. Gated access off a narrow unmade track, leading to the sea, takes you to y...
7 nights from £700
7 nights from £1500 *
Woodlands
45946 bedroom self catering home with sea views in Seaview, Isle of Wight.
This simply stunning four-storey, six bedroom house is situated in the village of Seaview within a few minutes' walk to the beach. With sea views from the top floor bedroom, Woodla...
7 nights from £1500 *
7 nights from £1000
1 Church House
45964 bedroom self catering cottage near the beach in Totland, Isle of Wight.
A simply stunning church conversion in Totland on the west coast of the Island and within walking distance to the beach, making this the perfect holiday destination. Beautifully co...
7 nights from £1000
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.