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

1 Harrow Cottages is a 1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £356

1 Harrow Cottages

4642

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


This charming first floor apartment is in Nettlestone, just up the hill from Seaview and within walking distance of the beach. Surrounded by countryside there are lovely views from...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £356

Mariners Cove is a 1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £416

Mariners Cove

3628

1 bedroom self catering apartment near the beach in Bembridge, Isle of Wight.


This charming one bedroom apartment forms part of a country house set around a shared Spanish-style courtyard, just outside the bustling village of Bembridge. With everything set o...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £416

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

Valdora is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Valdora

4959

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


Perfectly situated in the heart of the charming village of Seaview, Valdora is a gorgeous holiday retreat, beautifully styled to offer the very best in contemporary living. Seaview...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £554 *

Oceanix is a 1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £605

Oceanix

4900

1 bedroom self catering apartment with sea views in Ventnor, Isle of Wight.


A beautifully located top floor apartment in the heart of Ventnor, Oceanix provides the perfect seaside getaway for your next Isle of Wight holiday. The property has been though...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £605

19 Seaview Bay is a 1 bedroom self catering cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £717

19 Seaview Bay

4926

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


Escape to the delights of 19 Seaview Bay to enjoy a slice of stunning Island coastline, a gentle stroll around the pretty local shops, relax with an afternoon tea at Seaview Hotel ...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £717

The Cattle Byre is a 2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £606

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


The Cattle Byre has accommodation for three guests across two bedrooms, a double and a single. It has two private outdoor seating areas, the rear enclosed garden can only be access...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £606

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £505

6 St Josephs

3846

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £505

Grafton Cottage is a 2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.
  • Sleeps 4
  • Dogs welcome
  • Changeover Sat

7 nights from £508

Grafton Cottage

3501

2 bedroom, dog friendly cottage in a rural setting close to Godshill, Isle of Wight.


Located in a tranquil rural setting and part of Bagwich House, this sympathetic barn conversion is set over two floors and is one of three holiday properties. A short drive from th...

  • Sleeps 4
  • Dogs welcome
  • Changeover Sat

7 nights from £508

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  • 25% off

    25 May 2024 - 1 Jun 2024

    £984.00£738.00

Fir Cottage is a 2 bedroom self catering cottage near the beach in St Helens, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £508

Fir Cottage

3602

2 bedroom self catering cottage near the beach in St Helens, Isle of Wight.


Located in a quiet lane a few steps from St Helens village green, Fir Cottage is a refurbished Victorian semi-detached house, complete with all modern amenities. A great holiday ba...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £508

Oakham Cottage is a 2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight
  • Sleeps 4
  • Dogs welcome
  • Changeover Sat

7 nights from £508

Oakham Cottage

3516

2 bedroom, dog friendly holiday cottage in a rural setting close to Godshill, Isle of Wight


Oakham Cottage can be found in the heart of the Isle of Wight, surrounded by rolling countryside and the perfect location for exploring all treasures this lovely Island has to offe...

  • Sleeps 4
  • Dogs welcome
  • Changeover Sat

7 nights from £508

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