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

3 bedroom self catering cottage near the beach in Brook, Isle of Wight


Flackstead is a unique eco-friendly house which has breath-taking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of conte...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £1650 - £1950

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


If you long for picturesque walks in the daytime and quiet nights under starry skies, then Ashmead Cottage is your holiday ideal. This lovely property would suit a family or even t...

  • Sleeps 7 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £437

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

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


This light, beautifully presented holiday home offers quality accommodation with wooden floors, whitewashed walls and interesting prints and furnishings lending splashes of colour ...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £535

4 bedroom, rural self catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location, surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £670

3 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Montagu is a luxurious, upper ground floor apartment forming part of a converted Victorian villa, just seconds from the beach at Shanklin. With a private patio with sea views and a...

  • Sleeps 7 + cot
  • Regret no pets
  • Changeover Fri

Price per week £795 - £995

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


One of a handful of pretty pastel beach bungalows located in Salterns Village, Curlew Cottage is a small, exclusive development at the edge of Seaview that offers securew communal ...

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

Price per week £479

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


Large and modern, Skylark Cottage is one of the premium properties available at Salterns Village, an exclusive small gated development on the edge of Seaview. The village has a lov...

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

Price per week £479

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


Beautifully decorated in neutral tones throughout, Alcantara is a well-presented, spacious property offering flexible family accommodation. This detached property has a ground floo...

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

Price per week £500

We are Gold accredited with the Green Tourism Business Scheme.

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

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  • 20% off

    19 Oct 2018 - 26 Oct 2018

    £856.95 £685.56

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