Self catering holiday cottages for rent in 2026
7 nights from £1300
Newclose Houseboat
52003 bedroom houseboat with sea views in Bembridge, Isle of Wight
Welcome aboard Newclose Houseboat, a beautifully restored contemporary houseboat located in picturesque Bembridge harbour on the Isle of Wight, just a short stroll away from the st...
7 nights from £1300
7 nights from £1221
Apsley Cottage
51483 bedroom, dog friendly self catering cottage near Midhurst
Apsley Cottage is a welcoming cottage with a hot tub on the Cowdray Estate, situated in a secluded location just outside the picturesque village of Bepton, a short drive from Midhu...
7 nights from £1221
7 nights from £1848
Challens Yarde
51494 bedroom, dog friendly self catering cottage with hot tub near Midhurst
Challens Yarde is a Grade II Listed luxury holiday cottage with hot tub on the Cowdray Estate and can be found on a picturesque rural lane in the village of Easebourne, perfect for...
7 nights from £1848
7 nights from £547
10 Bayclose
51592 bedroom self catering apartment with sea views in Freshwater, Isle of Wight
Overlooking the gorgeous coastline at Freshwater Bay sits 10 Bayclose, a wonderfully homely apartment perfect for a family getaway to the seaside. With light and airy interiors, sn...
7 nights from £547
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 £780
The Drey
51393 bedroom self catering cottage near the beach in Seaview, Isle of Wight
Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...
7 nights from £780
From £223 per night *
Stargazers' Retreat
5125Luxury Yurt for 5 with sea views and outdoor bathtubs near Ventnor, Isle of Wight.
Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...
From £223 per night *
7 nights from £403
Sugar Beach
51022 bedroom dog friendly self catering cottage near the beach in Seaview, Isle of Wight
Seaview is a much sought-after charming village on the east of the Isle of Wight, and Sugar Beach is perfectly situated just a stone's throw from the beach and a short stroll away ...
7 nights from £403
7 nights from £763 *
Underwood Cabin
49953 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of ...
7 nights from £763 *
7 nights from £636
The Granary
50372 bedroom, dog friendly self catering cottage near Haywards Heath.
The Granary is situated beside a working organic farm, a short walk from the picturesque village of Cuckfield on the edge of the High Weald, an Area of Outstanding Natural Beauty (...
7 nights from £636
7 nights from £934 *
Sea Lights
49672 bedroom coastal holiday home, with sea views in Cowes, Isle of Wight.
Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet-friendly apartment...
7 nights from £934 *
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!
