Valentine's Breaks on the Isle of Wight
Let your partner know how much they mean to you by booking a retreat in a romantic cottage for two. Across the Isle of Wight, we have a range of beautiful self-catering cottages offering comfort, privacy and luxury so you can focus on what really matters: each other. Explore the Isle of Wight by day and return to your very own home-from-home together for a perfect Valentine's break.
Do as much or as little as you please during your romantic break on the Isle of Wight. Stroll hand-in-hand along the coast as the waves meet the shore and the breeze rustles your hair. There are lots of towns and villages to discover, and a huge number of country paths to wander before returning to your own slice of paradise. In a Classic cottage on the Isle of Wight, the choice is yours for a perfect getaway together. Let your Valentine know how special they are and book yourself a cottage to escape reality for a while. A Valentine break on the Isle of Wight will not disappoint.
Romantic Retreats on the Isle of Wight
At Classic Cottages we know a thing or two about holidays, and our luxury self-catering cottages offer the perfect base for a romantic getaway together. Whether you are planning on spending just a few days on the Isle of Wight, a week or longer, our cottages will provide you with homely touches and lots of modern comforts. Browse our list of 167 available cottages and find the right one for you and your beloved. All of our cottages are of the finest quality so your experience is the best it can be.
With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing
We have 167 Valentine's cottages on the Isle of Wight
Garsdon
36044 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
This bright, spacious detached house, on a quiet lane is just a 10 minute walk from the beautiful beach at Seagrove Bay. Furnished to a high standard, with four good-sized bedrooms...
Price per week £599
17 Sandcove Rise
35144 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
A spacious family home, 17 Sandcove Rise is located in a quiet cul-de-sac in the pretty village of Seaview. Well-presented and with modern furnishings throughout, it has a wonderfu...
Price per week £630
Mallards
36275 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...
Price per week £631 - £736
Middle Salterns
36314 bedroom, self catering cottage near the beach in Seaview, Isle of Wight.
Middle Salterns is a pretty, end of terrace Edwardian property in the heart of Seaview, simply decorated and arranged over three floors. There are two double bedrooms and a bunk-ro...
Price per week £643
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
Bay View
38054 bedroom, dog friendly holiday cottage with sea views in St Helens, Isle of Wight
Bay View is a charming semi-detached house situated down a quiet leafy lane off the Green in the picturesque village of St Helens and aptly named due to the stunning views over St ...
Price per week £675
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 gard...
Price per week £720 - £935
Hillside
36114 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Hillside is a traditionally furnished Victorian holiday home located conveniently close to the pretty beaches at Seagrove and Priory Bay. Spread over four floors, there is enough s...
Price per week £729
House of Logs
42254 bedroom, rural self catering cottage near the beach in Totland, Isle of Wight
House of Logs is a unique and stunning property located on the west coast of the Island, just a short walk from Widdick Chine and Totland Bay. Perfect for a peaceful holiday, the h...
Price per week £750
The Swallows
36804 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Spread over three floors The Swallows really is a beautiful family holiday home. The ground floor is very fresh, light and modern and has bi-folding doors leading out onto the pati...
Price per week £765
Cromwell Apartment
35893 bedroom self catering apartment with sea views in Shanklin, Isle of Wight.
Cromwell Apartment is a high end, beautifully presented, first floor apartment in a Victorian villa in Shanklin. Not your average beachfront apartment, the Cromwell comes with a de...
Price per week £795 - £995
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.