Romantic Breaks on the Isle of Wight

Pick a luxury bolthole with a bubbling hot tub, or how about one with a pool? Maybe a luxury retreat with spectacular sea views or perhaps a secluded romantic cottage just right for two? The choices are endless for a romantic getaway on the Isle of Wight. Browse through our collection and take a step closer to the holiday of your dreams together. Read more

The Isle of Wight offers an idyllic base for a romantic adventure. Miles of coast path to explore, beaches peppered with fossils, amazing restaurants and eateries and lots of fun attractions to discover. And best of all? You can enjoy your break with the one you love most in a romantic cottage for two.

So you can share the holiday of a lifetime together, we have a selection of 177 available self-catering cottages primed and ready to welcome you. From choosing your cottage to opening the front door, we will guide you through every step so that the whole process is as smooth as possible. All of our cottages are handpicked; personally inspected and fully equipped to ensure your total comfort during your romantic break on the Isle of Wight. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

Search through 177 available romantic retreats on the Isle of Wight

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

3 bedroom, rural self catering apartment near the beach near Newport, Isle of Wight


This stunning barn conversion is located just outside the picturesque village of Chillerton, in the heart of the Island’s farming community between Newport and Chale. The outlook o...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £505

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £550

3 bedroom, dog friendly self catering cottage in Ventnor.


This gorgeous stone cottage is nestled in a wonderful countryside location in the central south of the Island, a short distance from the coastal town of Ventnor. Situated at the en...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £550

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £561

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


An incredibly stylish three bedroom ground floor apartment ideally located a few minutes' walk from the village of Seaview and the beach. A lovely large entrance hall centrally fra...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £561

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £562

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


Dating back to 1863 and converted in 2011, this superb two-storey apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interior and the u...

  • Sleeps 5
  • Regret no pets
  • Changeover Sat

7 nights from £562

View
  • 10% off

    23 Feb 2019 - 2 Mar 2019

    £624.48 £562.03

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £570 *

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


The Old Boat House is an attractive period cottage, set in a fantastic waterfront location on the edge of the beach at Seagrove Bay. This charming family home has been tastefully d...

  • Sleeps 9 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £570 *

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £600

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


A very charming house overlooking The Green in the picturesque village of St Helens, on the east side of the Island, within a short and scenic walk to the beach. A footpath startin...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £600

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

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


10 Tollgate Cottages is a pastel coloured, beach bungalow set in a small gated development close to the waterfront. Clean, neutral decor and its close proximity to the beach make t...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £382.51 £306.00

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

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


27 Tollgate Cottages is one of a number of well presented, beachfront holiday bungalows situated in Salterns Village, a small gated development located opposite Seaview Duver and b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £382.51 £306.00

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

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


6 Tollgate Cottages is a bright and cheery cottage set in a small, gated development near the pretty village of Seaview. Close to the beach, local shops and bars, and with Cafe Blu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £306

View
  • 20% off

    22 Feb 2019 - 1 Mar 2019

    £382.51 £306.00

Choose from our exclusive collection at the best prices with real time availability.

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