Luxury Cottages for 4 People on the Isle of Wight

Luxury Cottages for 4 People on the Isle of Wight

Enjoy a luxury island retreat and book a holiday cottage for up to four people on the Isle of Wight. There's room for you and three of your nearest and dearest, and many of our cottages are dog-friendly too. Browse through our selection of 125 available self-catering cottages and take a step closer to the holiday of a lifetime.Read more

Spending time with our friends and family is really important, but it's not always that easy to get together and catch up. Holiday cottages provide great neutral ground in beautiful settings, away from the distractions of everyday life. Spend time together in a luxury self catering cottage sleeping up to 4 people and rediscover yourselves.

Self Catering Cottages on the Isle of Wight for Four People

At Classic Cottages we pride ourselves on marketing only the finest holiday cottages on the Isle of Wight. Each one of our self catering cottages is personally inspected and fully equipped to ensure your total comfort. Take your time looking through our collection of 125 available holiday cottages and find the perfect one waiting for you. 

We have 125 self catering cottages for 4 on the Isle of Wight

Lazydays Hideaway is a 1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Lazydays Hideaway

5381

1 bedroom glamping Yurt with sea views near Ventnor, Isle of Wight.


Welcome to Lazydays Hideaway, enjoying far reaching sea views across Reeth Bay and beyond and nestled on a hillside at the southerly point of the Isle of Wight. Whether you wan...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £180 per night

Halland Rise is a 4 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1359 *

Halland Rise

5500

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


Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...

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

7 nights from £1359 *

7 Sandpipers is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £603

7 Sandpipers

3568

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


Perfectly situated in the heart of the popular sailing village of Seaview on the eastern side of the Isle of Wight, 7 Sandpipers is a well-equipped town house set across three floo...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £603

Sunnyside is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £767

Sunnyside

4960

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


Perfectly situated in the much sought-after village of Seaview on the Isle of Wight, Sunnyside is an appealing dog friendly holiday abode fully refurbished in 2021/22. It is set in...

  • Sleeps 5 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £767

Sanderling is a 3 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £814

Sanderling

5424

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


A warm island welcome awaits at "Sanderling" a beautiful three bedroom home within a few minutes' walk of the beach and Seaview village, with the added bonus of a mature garden wit...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £814

Limpets  is a 3 bedroom self catering apartment with sea views in Seaview, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £832

Limpets

4622

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


This gorgeous home, just a stone's throw from the seafront, has sea views from the sitting-room and the luxury of your very own private garden, giving it all the ingredients for a ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Sat

7 nights from £832

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

10 Shanklin Manor is a 3 bedroom, rural self catering apartment near the beach in Shanklin, Isle of Wight.
  • Sleeps 5
  • No pets
  • Changeover Sat

7 nights from £834

10 Shanklin Manor

3511

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 first floor apartment is located on the outskirts of Shanklin. 10 Shanklin Manor has an elegant, monochrome interi...

  • Sleeps 5
  • No pets
  • Changeover Sat

7 nights from £834

Stargazers' Retreat is a Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1200

Stargazers' Retreat

5125

Luxury Yurt for 5 near the beach near Ventnor, Isle of Wight.


Welcome to Stargazers' Retreat, a heavenly glamping yurt nestled in rural splendour on the southerly tip of the Isle of Wight with blissful views of Reeth Bay and beyond. Situated ...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £1200

East Gull Sands 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 £512

East Gull Sands

3595

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


Seaview is a much sought-after and very charming village on the Isle of Wight and East Gull Sands sits in a magical position overlooking the beach, just a short stroll away from th...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £512

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

7 nights from £551

Lanthorn Cottage

4287

3 bedroom, dog friendly holiday cottage near the beach in St Helens, Isle of Wight


Located in a quiet side street just off the village green in St Helens, this cosy cottage offers great accommodation with a good sized garden, spacious decking and outdoor seating ...

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

7 nights from £551

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