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

3 bedroom self catering apartment with sea views in Shanklin, Isle of Wight.


Cromwell Apartment is a high end, beautifully presented, first floor apartment in a Victorian villa in Shanklin. Not your average beachfront apartment, the Cromwell comes with a de...

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

Price per week £795 - £995

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


With stunning sea views from not one but two balconies Solent View Road is a wonderful holiday destination within a few minutes' walk from Seagrove Bay. Located just on the outskir...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £825

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


Walnut Cottage is a real find if you're looking for a spot of luxury on holiday. Tucked away in central Seaview village Walnut offers spacious accommodation over two floors and an ...

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

Price per week £835

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


Tides Reach is a wonderful, newly modernised family house along the Seaview Duver just a short walk into Seaview Village and the Yacht Club. Tides Reach has a stylish open plan sit...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £850

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

4 bedroom, rural self catering cottage near the beach near Ventnor, Isle of Wight


Located in the village of Chale, in an area of outstanding natural beauty, The Mission is a truly unique property well worth a visit. The current owners have lovingly restored this...

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

Price per week £890

4 bedroom, dog friendly holiday cottage with sea views in Seaview.


Tucked away in the idyllic setting of Seagrove Bay and just steps away from the beach, Windy Ridge is a stunning house with wonderful sea views from both the first and second floor...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

Price per week £1000

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


This pretty attached Victorian cottage sits in the grounds of the Priory Estate and comes with use of its many diversions. With 70 acres of grounds to explore, plus a stunning priv...

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

Price per week £1013

4 bedroom self catering cottage with sea views in Seaview, Isle of Wight


A spectacular waterfront three-storey house situated on Seaview duver with uninterrupted sea views from the kitchen/dining-room and the first floor balcony. Just a few steps from y...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1100

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


This beautiful house is set in several acres of garden on the outskirts of Yarmouth, just a few minutes walk to the water’s edge, a truly stunning holiday destination. The property...

  • Sleeps 8 + 2 cots
  • Regret no pets
  • Changeover Sat

Price per week £1375

4 bedroom, rural self catering cottage with estuary views near Newport.


This superb property overlooks the River Medina from its corner plot in the exclusive Island Harbour development. Laid over four storeys the views across the River Medina are stunn...

  • Sleeps 8
  • Regret no pets
  • Changeover Fri

Price per week £1400

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

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