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 165 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 165 Valentine's cottages on the Isle of Wight

2 bedroom self catering apartment with sea views in Seaview, Isle of Wight.


The Crows Nest is a second floor apartment at the top of a Victorian property in the historic village of Seaview. A family looking for a convenient base from which to enjoy the Isl...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

Price per week £295

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


The Lobster Pot is a comfortably furnished beach bungalow located in a small waterside development on the edge of Seaview and next to a nature reserve. This beach bolt hole has dec...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £312

2 bedroom, dog friendly holiday cottage near the beach in Ventnor, Isle of Wight.


With an interesting history and dating from 1852, Trevessa was once a fishing cottage and overlooks the sea. The sitting-room, dining-room and both bedrooms have beautiful sea view...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £314

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £611.62 £489.60

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


Hove To is one of a small collection of bungalows located along the Seaview Duver. Situated on the corner, it benefits from a large decked area on two sides with a lovely outlook o...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £314

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

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


Cockleshells is one of the charming Salterns bungalows situated along the Seaview Duver within a short walk to the Yacht Club and Seaview Village. The new Owner has completely rede...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £314

2 bedroom self catering cottage near the beach in Seaview.


This delightful, stylish seafront bungalow is located in a front row position with wonderful views of the Solent and the beach is practically on the doorstep. Days at the seaside, ...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

Price per week £318

View
  • 15% off

    5 Oct 2018 - 12 Oct 2018

    £318.43 £270.30

  • 15% off

    12 Oct 2018 - 19 Oct 2018

    £398.61 £339.15

2 bedroom, dog-friendly holiday cottage with sea views in East Cowes, Isle of Wight


Smugglers' Run is a waterside property overlooking the River Medina and across to the sailing town of Cowes. Watch the boats sail by from the privacy of the balcony off the living-...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £321 - £374

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


Kitty Wake is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site ameniti...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £329

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


Wagtail is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site amenities ...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £329

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


Lapwing Cottage is a comfortable and neatly presented holiday bungalow located on the edge of the Salterns Holiday Village, in the charming village of Seaview. There are on site am...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £329

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