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 161 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 161 Valentine's cottages on the Isle of Wight

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

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


Rose Villa is a little gem of a home in Yarmouth with its open plan kitchen and dining-table close to the doors to the garden, capturing the light nicely on a sunny day. Continuing...

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

Price per week £520

View
  • 30% off

    15 Sep 2018 - 22 Sep 2018

    £571.30 £399.70

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

Don’t miss out; reserve your favourite 2019 holiday cottage for just £30

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


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

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


A seaside sanctuary, Shore House is a three-storey beautifully decorated house, with its own private heated swimming pool. Making the most of the far reaching views over the Solent...

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

Price per week £580

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in Seaview, Raleigh Cottage is complete with a cosy wood-burning stove for the cooler months, lovely decking for outside dining and ...

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

Price per week £625

View
  • 15% off

    31 Aug 2018 - 7 Sep 2018

    £900.06 £765.05

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


Right in the heart of Seaview village, this semi-detached property has been completely renovated, with a Skandi theme, to offer a wonderful place to stay on the Isle of Wight. With...

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

Price per week £630

View
  • 10% off

    31 Aug 2018 - 7 Sep 2018

    £1149.96 £1034.96

Our guests rate us 4.8/5 on Feefo, the independent review site.

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