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 167 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 167 Valentine's cottages on the Isle of Wight

2 bedroom thatched self catering cottage with sea views in Seaview.


If the restorative power of the sea appeals to you, 1 Thatched Cottage, with its uninterrupted views is an ideal holiday home. This 19th century property combines old world charm w...

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

Price per week £379

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

Price per week £380 - £434

3 bedroom rural self catering cottage near the beach in St Helens, Isle of Wight


Newlands is a charming detached cottage located just off the Green, in the picturesque village of St Helens. Its location is very peaceful yet within walking distance to the villag...

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

Price per week £383

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


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, Spinnakers is situated on a small private estate within walking ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £387

We’ve been raising the standards of self catering holidays since 1977.

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


Westbourne Cottage is a pretty, pastel-coloured, holiday cottage, located in the picturesque Seagrove Bay. The single level accommodation (ideal for less able guests) is lightly de...

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

Price per week £390

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £507.53 £406.02

2 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight


Bagwich Barn Cottage is located in a stunning setting within the grounds of the main house and with two other barns available for larger parties. A charming sun-room to the front o...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £395

2 bedroom, dog friendly holiday apartment with sea views in Ventnor, Isle of Wight.


Gilmerton is a charming and spacious apartment, beautifully decorated, and located on the outskirts of the vibrant town of Ventnor. The house is built into the hill so this first f...

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

Price per week £401

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


22 Seaview Bay is an impressive two-bedroom waterfront apartment, set over two floors in the prestigious Seaview Bay development. It would suit a family with children able to navi...

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

Price per week £403

2 bedroom, dog friendly houseboat on the sea in Bembridge Harbour, Isle of Wight.


For a holiday with a difference this is it! Situated on a private pontoon in Bembridge Harbour, you will have fond memories of your time on this unique floating home for years to c...

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

Price per week £412

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


7 Sandpipers is a modern townhouse, set in the heart of the popular sailing village of Seaview. Located just minutes from the seafront, with its beach, rock pools and coastal path,...

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

Price per week £420

View
  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £617.11 £493.68

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

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