We have 113 luxury self catering cottages for the October half term in South England
7 nights from £603
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 along with a spacious communal area. There are two bedrooms, a double and a twin, each bea...
7 nights from £603
Kingston Barns
7 nights from £2394
7 nights from £792
Medleys Barn
44762 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
Medleys Barn in High Hurstwood is an ideal base for exploring Ashdown Forest or for visits to Glyndebourne. Once a cart barn on a well-established fruit farm, this charming barn co...
7 nights from £792
7 nights from £1113 *
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 £1113 *
-
40% off
25 Oct 2025 - 1 Nov 2025
From £1512.00 £907.20
7 nights from £1048 *
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 £1048 *
7 nights from £608 *
Modwena
44683 bedroom, dog friendly self catering cottage near the sea in Yarmouth, Isle of Wight.
This gorgeous three bedroom cottage is in the picturesque town of Yarmouth just a few minutes' walk from the village centre and historic pier. Located on the west coast of the Isla...
7 nights from £608 *
7 nights from £583
Castlemans Stables East
44212 bedroom, dog-friendly self-catering cottage near Battle.
In the heart of East Sussex's 1066 countryside and set within the High Weald Area of Outstanding Natural Beauty, Castlemans Stables East is one of a pair of sympathetically convert...
7 nights from £583
7 nights from £583
Castlemans Stables West
44222 bedroom, dog-friendly self-catering cottage near Battle.
Set within the High Weald Area of Outstanding Natural Beauty, in the heart of East Sussex's 1066 countryside, Castlemans Stables West is one of a pair of sympathetically converted ...
7 nights from £583
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 £662
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Seaview is a wonderful place for an Isle of Wight holiday and Pebbles is perfectly situated in the heart of the village on a quiet residential street just a stone's throw away from...
7 nights from £662
7 nights from £837
Longdown Hall
43863 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...
7 nights from £837
