Cottages by the sea in Isle of Wight
Surrounded by the Solent and the Channel, the Isle of Wight has some wonderful sea views. Watch the sun rise and set over the ocean all from the comfort of your holiday cottage.Read more
Make your dream seaside holiday a reality with a holiday cottage less than one mile from the sea. With everything from romantic couples’ boltholes to huge mansions for family and friends, the Isle of Wight is the perfect place to find a cottage to suit your break.
Staying by the sea on the isle gives you a whole host of options when it comes to things to do. Walk along the promenades of Ventnor, Shanklin and Sandown or discover the yacht harbours of Cowes, East Cowes and Island Harbour. Staying in Brook puts you at the heart of an area of outstanding natural beauty and is a stone’s throw from plenty of coastal and inland walks. Not far from the needles you’ll find Freshwater Bay, supposedly one of the most stunning beaches on the island.
Yarmouth is a lovely place on the west of the island, staying close to the ferry port from Lymington will save you time on the journey and get you in the holiday mood sooner. To the north of the isle, you’ll also find Gurnard to the west of Cowes, right by the coast – some lovely views of the Solent.
Choosing a cottage by the sea will give you every opportunity to get out on to the coast and make the most of your holiday. With plenty of dog friendly beaches and family friendly activities, the Isle of Wight is an ideal location for a family summer holiday or come for an off season short break and enjoy the island when things are a little quieter. For couples, there are plenty of wonderful romantic locations where you can hide away, relax and slow down. Come in November for some fantastic winter walks and gloriously colourful sunsets. Try and spot a red squirrel before they go into hibernation and explore the isle’s historical locations, like Osborne House or Carisbrooke Castle.
We have 118 self catering cottages near the sea in Isle of Wight
7 nights from £356
1 Harrow Cottages
46421 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...
7 nights from £356
7 nights from £390
Mariners Cove
36281 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
This charming one bedroom apartment forms part of a country house set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. With everything set o...
7 nights from £390
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 £480
18 Seaview Bay
49961 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, 18 Seaview Bay is a charming, sunny apartment found in a small development close to the village...
7 nights from £480
7 nights from £525
Grace Cottage
42091 bedroom, dog friendly holiday cottage near the sea near Ventnor, Isle of Wight
This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...
7 nights from £525
7 nights from £550
19 Seaview Bay
49261 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel ...
7 nights from £550
7 nights from £554 *
Valdora
49593 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...
7 nights from £554 *
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
7 nights from £597
Buckland Cabin
48531 bedroom cabin near the beach in Seaview, Isle of Wight.
Tucked away just off the High Street in Seaview, this recently renovated and beautifully presented cabin is ideal if you are seeking a romantic hideaway for two. Step inside th...
7 nights from £597
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15% off
24 May 2024 - 31 May 2024
£955.00£811.75
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 £614
Bay View
39022 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
This beautiful contemporary apartment is literally perched above the beach, offering stunning views of the picturesque Freshwater Bay. Extremely well appointed, the apartment offer...
7 nights from £614
7 nights from £617 *
Escape Away
56122 bedroom luxury retreat with private hot tub
New to the Classic portfolio, very close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base you...
7 nights from £617 *