We have 26 self catering cottages near The Chequers Inn to show you...
7 nights from £861
10 Shanklin Manor
35113 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
This superb two-storey, first floor apartment dating back to 1863 is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the use of a la...
7 nights from £861
7 nights from £707 *
Sheldonia
51093 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...
7 nights from £707 *
7 nights from £888
St Albans House
39804 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...
7 nights from £888
7 nights from £493
Westhill View
48822 bedroom self catering cottage near the beach in Shanklin, Isle of Wight.
With the golden sands of Shanklin beach a short walk away, this lovely holiday home sits in the heart of town, perfect for traditional days by the seaside and within easy reach of ...
7 nights from £493
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 £1035
Sun Lodge
58534 bedroom, dog friendly holiday cottage with sea views in Ventnor.
Step back in time and immerse yourself in the historic charm of Ventnor at this elegant Isle of Wight retreat with mesmerising sea views and generous spaces for a truly relaxing fa...
7 nights from £1035
From £198 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 £198 per night *
From £145 per night
Lazydays Hideaway
53811 bedroom glamping Yurt with sea views and an outdoor bathtub near Ventnor, Isle of Wight.
Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...
From £145 per night
7 nights from £601
25 Palmerston Road
35383 bedroom self catering cottage near the beach in Shanklin.
Welcome to 25 Palmerston Road, a delightful holiday home perfectly situated in the charming town of Shanklin and just a short stroll away from the golden sandy beach and a good sel...
7 nights from £601
7 nights from £706
Bentinck
57243 bedroom cottage near the beach in Ventnor.
With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...
7 nights from £706
7 nights from £567
Oceanix
49001 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect seaside getaway for your next Isle of Wight holiday. The property has been though...
7 nights from £567
Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.
Quality inspections
We check our holiday homes to ensure that everything is up to our high standards for your holiday, from provision of our above standard minimum inventory to how fluffy the towels are, we make sure you’ll have a comfortable stay.
Hardworking teams of housekeepers will have the place spick and span, ready for your arrival, so when you get there you can just relax.
