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 76 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 76 Valentine's cottages on the Isle of Wight

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

7 nights from £481

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


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or several couples travel...

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

7 nights from £481

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

7 nights from £493

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


This gorgeous property is a stylishly converted coastguard cottage and really is a gem. Beautifully decorated throughout, in greys, blues and whites, it is an oasis of calm and has...

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

7 nights from £493

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £492.62 £394.09

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £500

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

7 nights from £500

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

7 nights from £587

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

7 nights from £587

Need more time? Reserve any cottage for up to 24 hours before booking.

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

7 nights from £592

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

7 nights from £592

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

7 nights from £595

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

7 nights from £595

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

7 nights from £637

3 bedroom self catering cottage near the beach in Seaview.


In a quiet position within a secluded courtyard in the village of Seaview, Raleigh Cottage is the perfect blend of old-world charm and contemporary comfort. It would suit a family ...

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

7 nights from £637

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  • 15% off

    22 Feb 2019 - 1 Mar 2019

    £637.46 £541.84

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

7 nights from £643

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

7 nights from £643

View
  • 10% off

    22 Feb 2019 - 1 Mar 2019

    £642.60 £578.34

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

7 nights from £663

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


A simply gorgeous three bedroom property just off St Helens' green on the eastern side of the Isle of Wight, The Haven is just a short walk from the coast and a ten minute stroll t...

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

7 nights from £663

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £445

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


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £445

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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