Cottages near Osborne Bay

Cottages near Osborne Bay

We've got 11 holiday cottages within 5 miles of Osborne Bay. You can refine your search using the controls below.

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

We have 11 self catering cottages near Osborne Bay to show you...

Barton Manor Lake Cottage is a 2 bedroom, dog friendly holiday cottage near the beach in East Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £745

Barton Manor Lake Cottage

3581

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


Steeped in history Barton Manor is of great significance to the Isle of Wight’s heritage, situated adjacent to Osborne House and part of the original estate. The grand driveway lea...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £745

Barton Manor Farmhouse is a 4 bedroom, dog friendly Farmhouse with access to a private beach in East Cowes, Isle of Wight.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1610 *

Barton Manor Farmhouse

3580

4 bedroom, dog friendly Farmhouse with access to a private beach in East Cowes, Isle of Wight.


Set in the stunning grounds of The Barton Manor Estate, with access to a private beach, 200 acres of woodland and close to Cowes on the Isle of Wight, Barton Manor Farmhouse is a b...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1610 *

Winkle Cottage is a 2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £628

Winkle Cottage

4395

2 bedroom self catering cottage near the beach in Cowes, Isle of Wight.


This gorgeous terraced cottage, situated in the Conservation Area of the old town of Cowes, is just a few minutes' walk from the centre of town, offering the perfect family holiday...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £628

Little Field is a 3 bedroom, dog friendly holiday cottage near the beach near Ryde.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £755 *

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £755 *

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Creekside is a 5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.
  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

Creekside

3588

5 bedroom, dog friendly holiday cottage with sea views in Wootton, Isle of Wight.


Aptly named and perfectly positioned on the banks of pretty Wootton Creek on the north coast of the Isle of Wight, Creekside is a gorgeous waterfront holiday home with delightful v...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1157

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

7 nights from £510 *

Lucaster

4307

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


This gorgeous, cosy, former coastguard's cottage sits in a peaceful setting in Fishbourne and is just a few yards from the sea and the welcoming local pub. Lucaster is perfectly pl...

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

7 nights from £510 *

Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £547

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 £810

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 £810

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

7 nights from £934 *

Sea Lights

4967

2 bedroom coastal holiday home, 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 £934 *

Keepers Cottage is a 4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £877

Keepers Cottage

4070

4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £877

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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A private beach accessed only from Osborne House where you will pay an entry fee. The beach is sandy and safe, a favourite of Queen Victoria and her children when they were in residence. These days you can take a look at her bathing hut and enjoy an ice cream on the beach. A shuttle bus runs from the house between April - October. There's no lifeguard cover and dogs are not allowed.