Holiday cottages for 2025 in Isle of Wight

Holiday cottages for 2025 in Isle of Wight

Ready to start planning your 2025 adventure? Choose from a growing collection of holiday cottages across the UK. So, where will 2025 take you? Read more

Long, leisurely countryside walks, exploring somewhere new, the warm sand between your toes, finding sun-soaked spots for lazy afternoon picnics and taking the time to enjoy those special sunrises and sunsets. Sound good? Whether you're looking for a coastal holiday or a rural retreat, or a cottage with a hot tub or swimming pool, we have a portfolio of properties ready and waiting for you to start planning your next self catering holiday in Isle of Wight. 

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

Self catering holiday cottages for rent in 2025

Pucks Oak is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1050

Pucks Oak

5698

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


Within moments of the seafront at Seaview, with off-street parking and a lovely garden, semi-detached Pucks Oak is a great home-from-home to enjoy with friends and family. With the...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1050

The Old Dairy

  • Sleeps 7 + 2 cots in 2 properties
  • Changeover Fri

7 nights from £1022

The Studio is a 1 bedroom, dog friendly, cosy cottage near Ryde.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £372

The Studio

5753

1 bedroom, dog friendly, cosy cottage near Ryde.


Whether you seek relaxation or adventure on the Isle of Wight, The Studio provides the most welcoming modern-rustic retreat to experience the best of natural beauty and contemporar...

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

7 nights from £372

Bentinck is a 3 bedroom cottage near the beach in Ventnor.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £743

Bentinck

5724

3 bedroom cottage near the beach in Ventnor.


With everything you could wish for on your doorstep for a blissful Isle of Wight holiday experience with family or friends, Bentinck is a great base to explore all that this Island...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £743

Pepita is a 5 bedroom, dog friendly holiday cottage with sea views in Seaview.
  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1469 *

Pepita

5719

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


With breathtaking sea views and the beach only a few steps from the front door, two former coastguard cottages and the adjoining boathouse have been transformed into an island gem,...

  • Sleeps 9 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1469 *

The Dairy is a 3 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £982

The Dairy

5631

3 bedroom self catering cottage near the beach in Seaview.


Set in the pretty village of Seaview, moments from the seafront, this delightful home-from-home is waiting to welcome you. The village centre is a short stroll away, here you will ...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £982

The Observatory is a 4 bedroom self catering apartment near the beach in Seaview.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1152 *

The Observatory

5693

4 bedroom self catering apartment near the beach in Seaview.


What a view! The most perfect seascape vistas will be found from this pretty apartment in the heart of the traditional seaside village of Seaview. This quirky home-from-home is the...

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

7 nights from £1152 *

Sunrise and Stars is a Dog friendly shepherds hut with a hot tub near Ventnor.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £85 per night

Sunrise and Stars

5672

Dog friendly shepherds hut with a hot tub near Ventnor.


Step into an oasis of peace and tranquility on the Isle of Wight at Sunrise and Stars, a beautifully crafted hideaway with a pool for private use and a hot tub, surrounded by capti...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

From £85 per night

We are Gold accredited with the Green Tourism Business Scheme.

Tangle Cottage is a 4 bedroom self catering cottage near the beach in Seaview.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £728 *

Tangle Cottage

5669

4 bedroom self catering cottage near the beach in Seaview.


Nestled at the end of Ryde Road, just a short walk from the beach and Seaview village, with off-street parking and a lovely large garden to the rear, semi-detached Tangle Cottage i...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £728 *

Inglefield is a 4 bedroom, dog friendly holiday cottage near the beach in St Helens.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £908

Inglefield

5637

4 bedroom, dog friendly holiday cottage near the beach in St Helens.


This beautiful home close to Bembridge Harbour is a space to enjoy with family and friends. From exploring the bays and beaches to the rolling countryside and historic castles, Ing...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £908

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