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 69 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 69 Valentine's cottages on the Isle of Wight

We are no longer accepting new bookings for holidays arriving before the 4th June. COVID-19

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.


This charming one bedroom apartment forms part of a country house, set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. You can enjoy th...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £287

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £336

1 bedroom self-catering cottage near Ventnor, Isle of Wight


Located in a rural village setting, Berryl Mead View is a delightful home from home cottage with plenty of space. It is well-equipped throughout and has an extremely comfortable li...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £336

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

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

7 nights from £366

2 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


Located in the cosmopolitan town of Ventnor in a Victorian townhouse, Seascape is a modern two bedroom apartment with spectacular sea views along the coastline. It offers contempor...

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

7 nights from £366

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

7 nights from £373

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


5 Sandpipers is a well-equipped, modern house set within a small development in the heart of Seaview. It offers comfortable accommodation for a couple or small family. The sitt...

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

7 nights from £373

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £373

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


Quiet Corner is a modestly furnished, comfortable cottage situated in the popular village of Bembridge, less than a mile from Bembridge beach. As its name suggests it's tucked away...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £373

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, Dairy Cottage is a light and airy single-storey cottage with plenty of charm throughout. The double bedroom has pleasant views across the far...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


Originally the farm's milking parlour, this delightful semi-detached cottage sleeping four is the perfect cottage to spend quality time together as a family in a stunning rural loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £379

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

7 nights from £385

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


4 Carina is a modestly furnished, first floor apartment in a converted house which offers a great value break for families or a couple. Centrally located just yards from the shops ...

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

7 nights from £385

We are Gold accredited with the Green Tourism Business Scheme.

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


A barn conversion in a rural setting, you'll enjoy a feeling of peace from the moment you step inside this lovely retreat, with its exposed beams and rustic decor. Sitting with...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £388

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £398

2 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight


If you are looking for a traditional cottage, look no further than Blakes Barn. Constructed from Island stone, the charm starts outside Blakes Barn with the beautiful brick work, t...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £398

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