Holiday Cottages in a Town in Isle of Wight
Holidays in a town offer you the balance of having local pubs, cafes and restaurants nearby and the countryside and coast just a short journey away. If you like to leave the car at home, our holiday homes in towns have a good selection of things to do right on your doorstep so you’ll be able to get around by walking or taking public transport. Town cottages are perfect for people who want local activities and shops nearby.
We have 21 self catering cottages in a town in Isle of Wight.
7 nights from £599
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 £599
7 nights from £884
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 £884
7 nights from £1654
Beachside
51003 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
Welcome to your Island idyll, beautifully styled to offer contemporary seaside living at its best and perfectly situated on the beachfront in the heart of the much sought-after tra...
7 nights from £1654
7 nights from £1374
Firestone Lodge
54944 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...
7 nights from £1374
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 £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 £1458
Leeway House
51384 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight
Renowned as home to the largest sailing regatta in the world, Cowes is a pretty seaport town on the north side of the Isle of Wight, with fabulous views over the Solent and a great...
7 nights from £1458
7 nights from £1390
Mountbatten Garden Apartment
36354 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.
Mountbatten Garden Apartment is a fabulous apartment stylishly furnished with four en suite bedrooms and comes with a private courtyard including a six person hot tub. Vibrantly de...
7 nights from £1390
7 nights from £1415
Seacrest House
36535 bedroom, rural self catering cottage near the beach in Ryde, Isle of Wight.
This stunning three-storey holiday home is in the enviable position of being only a few minutes' stroll from the beach and also the centre of Ryde town. Built in the early part of ...
7 nights from £1415
7 nights from £1773
Harbour View
47314 bedroom self catering cottage with sea views in Ryde, Isle of Wight.
Escape to the Isle of Wight for a blissful coastal retreat at Harbour View, an impressive Grade II Listed townhouse with stunning sea views, spread over three floors, and with the ...
7 nights from £1773
7 nights from £2006
Solent Heights
39465 bedroom self catering cottage near the beach in Cowes, Isle of Wight
A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...
7 nights from £2006
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!
