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 157 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 157 Valentine's cottages on the Isle of Wight

4 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


A smart town house, with well presented accommodation for eight set over three floors, Lucaya offers a great space with a pretty enclosed rear patio and lawn for an extended family...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £532

3 bedroom, dog friendly holiday cottage with sea views in Brook, Isle of Wight


This pretty detached cottage can be found on a quiet lane in Brook on the south west coast. With its large, mature garden overlooking adjacent farmland, and close proximity to mile...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £569

We are Gold accredited with the Green Tourism Business Scheme.

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


This bright, spacious detached house, on a quiet lane is just a 10 minute walk from the beautiful beach at Seagrove Bay. Furnished to a high standard, with four good-sized bedrooms...

  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £599

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


A spacious family home, 17 Sandcove Rise is located in a quiet cul-de-sac in the pretty village of Seaview. Well-presented and with modern furnishings throughout, it has a wonderfu...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £630

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


Mallards is a spacious, three-storey Edwardian house in Seaview village and a much-loved family home. Enjoying a great location just yards from the seafront, it's the perfect choic...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £631 - £736

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


Middle Salterns is a pretty, end of terrace Edwardian property in the heart of Seaview, simply decorated and arranged over three floors. There are two double bedrooms and a bunk-ro...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Sat

Price per week £643

4 bedroom, dog friendly holiday cottage with sea views in St Helens, Isle of Wight


Bay View is a charming semi-detached house situated down a quiet leafy lane off the Green in the picturesque village of St Helens and aptly named due to the stunning views over St ...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £675

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor with the most breathtaking views from virtually every room. The beautiful tiered gard...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £720 - £935

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

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


Hillside is a traditionally furnished Victorian holiday home located conveniently close to the pretty beaches at Seagrove and Priory Bay. Spread over four floors, there is enough s...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £729

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


Spread over three floors The Swallows really is a beautiful family holiday home. The ground floor is very fresh, light and modern and has bi-folding doors leading out onto the pati...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

Price per week £765

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