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 126 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 126 available holiday cottages and find the perfect one waiting for you. 

We have 126 self catering cottages for 4 on the Isle of Wight

Daisy Cottage  is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £840

Daisy Cottage

4824

2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.


Daisy Cottage is a lovely cosy and welcoming mid terrace cottage nestled in the heart of Bembridge. Located in one of the most desirable areas to live in on the Isle of Wight, this...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £840

Weirside Cottage is a 2 bedroom, dog friendly holiday cottage near the beach near Yarmouth.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £852

Weirside Cottage

5320

2 bedroom, dog friendly holiday cottage near the beach near Yarmouth.


As pretty as a picture, feast your eyes on Weirside a stunning Grade II Listed cottage at the heart of the idyllic island village of Brighstone, just half mile from the sea and the...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £852

Sea Lights is a 2 bedroom self catering apartment with sea views in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £987

Sea Lights

4967

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


Situated close to the beating heart of world-famous Cowes, lies the pretty coastal village of Gurnard, where you will find this handsome coastal ground floor pet friendly apartment...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £987

Starboard Side is a 2 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £994

Starboard Side

4736

2 bedroom, dog friendly holiday cottage near the beach in Cowes, Isle of Wight.


This gorgeous and beautifully presented cottage is within walking distance of lovely Gurnard beach and has wonderful sea views from the first floor main bedroom. The owner of Starb...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £994

Our property managers are local experts who handpick perfect places to stay.

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1018

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach and not far from the iconic Needles, Escape Away is the perfect retreat to base yourself for a peaceful holiday. Whisk yourself away to the glorious Isle of Wigh...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1018

View
  • 25% off

    29 Mar 2024 - 5 Apr 2024

    £1443.00£1082.25

  • 25% off

    5 Apr 2024 - 12 Apr 2024

    £1443.00£1082.25

Driftwood is a 2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1018

Driftwood

5613

2 bedroom, dog friendly holiday cottage near the beach in Freshwater, Isle of Wight.


Whisk yourself away to this pretty retreat on the glorious Isle of Wight, perfect for couples and families and your four-legged companions who love to explore as there is plenty to...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1018

View
  • 25% off

    29 Mar 2024 - 5 Apr 2024

    £1443.00£1082.25

  • 25% off

    5 Apr 2024 - 12 Apr 2024

    £1443.00£1082.25

Dolphin Cottage is a 4 bedroom self catering cottage near the beach in Bembridge, Isle of Wight
  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1179 *

Dolphin Cottage

4347

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


Within a few minutes’ walk of the village centre and located on an unmade road leading to the sea, Dolphin Cottage is a simply stunning house ideally laid out to make space for all...

  • Sleeps 8 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1179 *

Oystercatcher is a 3 bedroom houseboat in Bembridge, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1188 *

Oystercatcher

4869

3 bedroom houseboat in Bembridge, Isle of Wight.


Set in picturesque Bembridge Harbour with far reaching views out to the Solent, Oystercatcher is a luxurious houseboat, beautifully furnished and just waiting to welcome you on boa...

  • Sleeps 6
  • No pets
  • Changeover Fri

7 nights from £1188 *

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 £1338 *

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 £1338 *

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

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