We've found 76 self catering cottages for Christmas and New Year on the Isle of Wight.
7 nights from £633
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 £633
7 nights from £1788
Saye House
45734 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Just a few minutes from idyllic Seagrove Bay, Saye House has been stylishly renovated to a high standard offering a wonderful place to enjoy a well-earned rest on the Isle of Wight...
7 nights from £1788
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £2143
Redworth
45415 bedroom self catering home near the beach in Bembridge, Isle of Wight.
This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...
7 nights from £2143
7 nights from £568
The Cattle Byre
45352 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...
7 nights from £568
7 nights from £655
The Dairy
45362 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...
7 nights from £655
7 nights from £601
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £601
7 nights from £601
The Pigsty
45382 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
The Pigsty is a detached barn with parking for two cars and two private seating areas alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...
7 nights from £601
Kingston Barns
7 nights from £2425
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
7 nights from £1246
Solas
44594 bedroom self catering cottage with sea views in Seaview, Isle of Wight.
This superb, spacious detached house close to Seaview village has wonderful sea views from the first floor open plan sitting/dining-room and balcony. Taking full advantage of the v...
7 nights from £1246
7 nights from £1804
Windy Ridge
44644 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning semi-detached house with wonderful sea views from both the ground a...
7 nights from £1804
