Holiday cottages with 2 bedrooms in Isle of Wight

Holiday cottages with 2 bedrooms in Isle of Wight

We’ve picked out 109 perfect holiday cottages with 2 Bedrooms in Isle of Wight. Read more

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

We have 109 self catering cottages with 2 bedrooms in Isle of Wight

6 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £427 *

6 St Josephs

3846

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


6 St Josephs is a top floor apartment with stunning panoramic sea views, which you can admire from the balcony, sitting-room and main bedroom! Ideally positioned between Bonchurch ...

  • Sleeps 4 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £427 *

1 Thatched Cottage is a 2 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £521 *

1 Thatched Cottage

3508

2 bedroom thatched, self catering cottage with sea views in Seaview, Isle of Wight.


If the restorative power of the sea appeals to you, 1 Thatched Cottage with its uninterrupted views is an ideal holiday home. This 19th Century semi-detached property combines old ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £521 *

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 Fri

7 nights from £534 *

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 Fri

7 nights from £534 *

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  • 50% off

    1 Sep 2025 - 8 Sep 2025

    From £901.85 £450.92

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 £554 *

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 £554 *

1 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £564

1 St Josephs

4183

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


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £564

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 £640 *

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 much as you do. Th...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £640 *

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 £670 *

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 £670 *

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 £672 *

Daisy Cottage

4824

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


In prime position in a row of pretty cottages, ideally situated in the centre of charming Bembridge on the beautiful Isle of Wight, Daisy Cottage is perfectly placed just a short s...

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

7 nights from £672 *

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Underwood Cabin is a 3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £687 *

Underwood Cabin

4995

3 bedroom, dog friendly self catering cottage near Yarmouth, Isle of Wight.


Nestled next to St Hubert's Lodge surrounded by tranquil woodlands and green pastures, Underwood Cabin is a delightful rural retreat, perfectly situated on the edge of the Isle of ...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £687 *

Sheldonia is a 3 bedroom self catering cottage with sea views in Ventnor, Isle of Wight.
  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £707 *

Sheldonia

5109

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


Welcome to Sheldonia, a hidden gem in the delightful seaside town of Ventnor and within touching distance of Steephill Cove - one of the Island's prettiest beaches, featured in The...

  • Sleeps 6
  • No pets
  • Changeover Sat

7 nights from £707 *

Load more

Holiday cottages with 2 bedrooms are perfect for a small family to relax in on their annual getaway, or two sets of couples who’d rather not argue over who gets the sofa bed (we don’t do sofa beds. Or fold up beds. Or even pull out beds). Maybe there are only two of you, but you appreciate the extra space, especially when one of you starts to snore…

Whatever you are planning on using the second bedroom for, the beds will be made up with fresh linen and clean towels ready and waiting (all our cottages provide linen and towels as standard). We’ve two bedroom cottages with double beds, twin beds, single beds and even zip-and-links – so there is bound to be a two bedroom holiday cottage in Isle of Wight that suits your needs. Use the filters on the left to help find the right one for you.