Cottages on the Isle of Wight Sleeping 5 People

Cottages on the Isle of Wight Sleeping 5 People

Open the door to a Classic cottage on the Isle of Wight and feel yourself relax. All of our cottages are perfectly kitted out, combining home comforts and modern luxuries so that you can enjoy total comfort during your stay. Choose four of your favourite people or simply indulge in some extra space, our self-catering holiday cottages for 5 people are primed and ready for you on the Isle of Wight. Read more

Spring, summer, autumn and winter, a holiday on the Isle of Wight always delivers. Choose your favourite cottage from our selection and let the good times roll. Whether you are looking for a solo retreat for some gentle contemplation and relaxation, a family holiday or a catch up with friends, we'll find something for you amongst our collection of luxury cottages for 5 people. From spontaneous short breaks to holidays planned in advance with lots of time for excitement to build, give yourself something to look forward to. 

From country to coast the Isle of Wight offers a diverse and beautiful escape. Spend your days exactly the way you want to and enjoy the holiday of a lifetime. It's good news for your four-legged friend too as many of our holiday cottages are dog-friendly. 

Holiday Cottages for 5 People on the Isle of Wight 

At Classic Cottages we pride ourselves on the quality of our cottages and make sure only the best are on our books. To maintain our standards, we personally inspect and handpick all of our cottages. Each one is fully equipped with a full inventory, and everything you could need for your holiday is provided. So your experience is as relaxed and easy as can be, we provide help and support every step of the way. Get in touch to find out more. 

Choose from 83 luxury cottages for 5 people on the Isle of Wight

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

7 nights from £667

Pandora Lodge

3642

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


Perfectly situated in the heart of the delightful village of Seaview on the Isle of Wight, Pandora Lodge is a lovely, spacious ground floor apartment forming part of a larger prope...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £667

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

7 nights from £691

Trevenna

3686

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


Trevenna is a thoughtfully designed holiday home in Seaview that really delivers when it comes to space, charm and comfort. It would be ideal for a family or couples travelling tog...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £691

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

7 nights from £725

3 Springfield Court

3547

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


With a comfortable interior, an unbeatable location, manicured grounds and the beach within easy reach, 3 Springfield Court has it all. This delightful holiday home would suit a fa...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £725

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 £739

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 £739

We’re here to help you find your perfect place to stay 7 days a week.

Blackberries is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £739

Blackberries

3583

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


A warm Isle of Wight welcome awaits you at Blackberries a pretty coastal cottage which offers a peaceful escape for families, small groups or couples alike in the delightful sailin...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £739

23 Coastguard Cottage is a 3 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £742

23 Coastguard Cottage

3534

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


Welcome to 23 Coastguard Cottage, a delightful holiday abode perfectly situated just a hop, skip and a jump away from stunning Forelands beach in Bembridge and a great base for a f...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £742

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

7 nights from £764

30 Seaview Bay

3549

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


If you're searching for a place to stay by the sea, 30 Seaview Bay could be just the spot. Perched just steps away from the enchanting Seagrove Bay and Seaview Bay, this sunny apar...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £764

Beggars Roost is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £775

Beggars Roost

4346

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


This gorgeous first floor apartment in the heart of Seaview village is perfectly placed to reach everything within a few minutes' walk. The seafront is just around the corner, a po...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £775

Longdown Hall is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £777

Longdown Hall

4386

3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight


A stunning property in Ventnor on the southern tip of the Island, with the most sensational 180 degree sea views from the sun-drenched patio. Relax with your breakfast in the sunsh...

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

7 nights from £777

The Drey is a 3 bedroom self catering cottage near the beach in Seaview, Isle of Wight
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

The Drey

5139

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


Located in the grand building that is Springfield Court, guests staying in this lovely holiday home can take full enjoyment of the grounds during their stay. Comfortably furnished ...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £780

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

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