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.Read more
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 68 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.
We have 68 Valentine's cottages on the Isle of Wight
7 nights from £527
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 £527
7 nights from £556
Solent View Cottage
43892 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This charming two bedroom cottage is situated in the pretty coastal village of Gurnard, just outside Cowes, home to some spectacular Solent views and a prime location to watch the ...
7 nights from £556
7 nights from £562
Yardley
36972 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
Yardley is a charming Victorian cottage, set in the centre of the pretty sailing village of Seaview. The beach and local shops are only a few minutes from your doorstep making this...
7 nights from £562
7 nights from £579
Spinnakers
36592 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.
A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, semi-detached Spinnakers is situated on a small private estate w...
7 nights from £579
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50% off
6 Dec 2024 - 13 Dec 2024
£599.00 £299.50
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.
7 nights from £628
Winkle Cottage
43952 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes walk from the centre of town, offering the perfect family holiday ...
7 nights from £628
7 nights from £633
Pinings Yard
46252 bedroom self catering cottage near the beach in Yarmouth, Isle of Wight.
This gorgeous, tucked away cottage is just a short stroll from the centre of Yarmouth and a real delight. Gated access off a narrow unmade track, leading to the sea, takes you to y...
7 nights from £633
7 nights from £641
The Stables
45372 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...
7 nights from £641
7 nights from £641
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 alongwith a spacious communal area. There are two bedrooms, a double and a twin, each beau...
7 nights from £641
7 nights from £643
1 Starboard House
35072 bedroom, rural self catering cottage near the beach in Seaview, Isle of Wight.
If you're looking for a property that's practically on the beach, then this is it! 1 Starboard House perches just opposite the beach in the centre of Seaview village and enjoys uni...
7 nights from £643
7 nights from £650
Pebbles
43982 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
This beautifully refurbished house is perfectly situated in the heart of Seaview Village, with a lovely patio area to the rear and outdoor seating so you can enjoy dining in the Is...
7 nights from £650
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.
