Valentine's Breaks on the Isle of Wight

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 75 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. 

We have 75 Valentine's cottages on the Isle of Wight

West Ingle is a 5 bedroom self catering home near the beach in Seaview, Isle of Wight.
  • Sleeps 11 + cot
  • No pets
  • Changeover Sat

7 nights from £1701

West Ingle

3693

5 bedroom self catering home near the beach in Seaview, Isle of Wight.


A beautiful Edwardian house, brimming with charm and original features, with magnificent sea views from almost every room, the terrace and garden. The open plan kitchen/dining-room...

  • Sleeps 11 + cot
  • No pets
  • Changeover Sat

7 nights from £1701

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  • 40% off

    25 May 2024 - 1 Jun 2024

    £3295.00£1977.00

Redworth is a 5 bedroom self catering home near the beach in Bembridge, Isle of Wight.
  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2182

Redworth

4541

5 bedroom self catering home near the beach in Bembridge, Isle of Wight.


This impressive five bedroom house is located on Ducie Avenue, a charming unmade road leading to the beach, in the village of Bembridge. Located within a few minutes walk of the lo...

  • Sleeps 11 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £2182

St Andrews is a 6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.
  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £3150

St Andrews

4641

6 bedroom, dog friendly holiday home with hot tub near the beach in Yarmouth, Isle of Wight.


Wow! This spectacular converted church has the makings for the most amazing holiday, set in an elevated position with panoramic views across the surrounding countryside and a glimp...

  • Sleeps 12 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £3150

Bagwich House

  • Sleeps 8 + 2 cots in 2 properties
  • Changeover Sat

7 nights from £1016

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

Kingston Barns

  • Sleeps 15 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £2587