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 168 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. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 168 Valentine's cottages on the Isle of Wight

3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight


This charming cottage is tucked away down an unmade road just off Bembridge Harbour, within walking distance of Bembridge village centre. The front and rear gardens of Old Railway ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £495

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

Price per week £500

3 bedroom self catering cottage near the beach in St Helens, Isle of Wight


Primrose Cottage is a fully modernised and beautifully furnished Victorian three bedroom cottage situated just off the green in St Helens and offering everything you might need for...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £504

3 bedroom self catering apartment near the beach in Seaview.


Perched right on the waterfront opposite Seaview beach, 3 Quay Rocks has unrivalled views of the attractive seafront and beyond, out to the ships passing by on the Solent. The apar...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £510

Our property managers are local experts who handpick perfect places to stay.

3 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.


Rose Villa is a beautifully appointed home in the heart of the village of Yarmouth. It would ideally suit a family or friends traveling together. This spacious property offers ...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £520

3 bedroom, dog friendly cottage near the beach in East Cowes, Isle of Wight.


This truly lovely holiday home, with a wood-burner, is a great choice whatever the season. 1 Barton Lodge is a beautiful property which has been lovingly restored with your comfort...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £544

3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight


A lovely three bedroom house in the heart of Seaview village within a few minutes walk to the seafront and Seaview Yacht Club. Beautifully decorated throughout with an open plan li...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £550

3 bedroom, rural self catering cottage near the beach in Merstone, Isle of Wight.


The Barn, a linked country cottage with a rustic interior and some exposed wooden beams, is located on the outskirts of Merstone and just minutes from the quaint village of Godshil...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

Price per week £565 - £765

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight


Located on the corner of Ryde Road, Westbourne is a lovely property ideally placed for Seaview Village and the beach. The village amenities are just a few minute's stroll away and ...

  • Sleeps 6 + 2 cots
  • Regret no pets
  • Changeover Fri

Price per week £575

3 bedroom self catering cottage near the beach in Seaview, Isle of Wight


Bay Cottage is a lovely three bedroom detached property on the outskirts of Seaview village, located in Seagrove Manor Road, a quiet spot yet just a few minutes walk into the villa...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

Price per week £575

We’ve been raising the standards of self catering holidays since 1977.

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