Cottages with Enclosed Gardens on the Isle of Wight

Cottages with Enclosed Gardens on the Isle of Wight

Have your own little bit of the Isle of Wight marked out just for you with a holiday cottage that has an enclosed garden. If you have children in your party or would like to bring your canine chum to a dog-friendly cottage, then our enclosed-garden properties may hold the key. Pour through our available cottages and let your imagination run wild. A dream holiday is just around the corner.   Read more

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

We have 42 Isle of Wight cottages with enclosed gardens

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 £827 * booking fees included

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 £827 *

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 £998 * booking fees included

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 £998 *

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The Cattle Byre is a 2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £651 booking fees included

The Cattle Byre

4535

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


Tucked away in a peaceful rural setting on the west side of the island, The Cattle Byre is a beautifully converted barn that blends rustic charm with modern comfort. Perfect for a ...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £651

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

7 nights from £487 booking fees included

Faithfull Cottage

3600

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


Faithfull Cottage is a welcoming retreat situated within two miles distance of St Helens village on the Isle of Wight, as well as a gorgeous beach, RSPB Nature Reserve and the vill...

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

7 nights from £487

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Quiet Corner Cottage is a 2 bedroom, dog friendly holiday cottage near the beach in Bembridge, Isle of Wight.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £602 booking fees included

Quiet Corner Cottage

3646

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


Bembridge is a much sought-after pretty village on the east of the Isle of Wight and Quiet Corner Cottage is a cosy semi-detached bungalow, perfectly situated just a mile from the ...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £602

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

7 nights from £667 booking fees included

Spinnakers

3659

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


Situated in a peaceful, private estate just a short stroll from the charming seaside town of Yarmouth, Spinnakers is a cosy, single-storey semi-detached holiday home with well-kept...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £667

The Dairy is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £669 booking fees included

The Dairy

4536

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


The dairy is a warm and welcoming barn conversion perfect for slow mornings, costal adventures and cosy evenings by the fire. Being is the largest of the four barns at Kingston, an...

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

7 nights from £669

The Pigsty is a 2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £672 booking fees included

The Pigsty

4538

2 bedroom, dog friendly cottage near the beach near Brighstone, Isle of Wight.


Tucked away in a picturesque and peaceful spot just outside the village of Shorwell, this charming barn conversion makes a wonderful base for a relaxed getaway. The Pigsty at Kings...

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

7 nights from £672

The Stables  is a 2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £672 booking fees included

The Stables

4537

2 bedroom, dog friendly self catering cottage near Brighstone, Isle of Wight.


The heart of the property is an inviting open plan living space where the sitting, dining and kitchen areas are thoughtfully brought together. Soft natural light filters in through...

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

7 nights from £672

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 £715 booking fees included

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 £715

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

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A holiday cottage with an enclosed garden can provide a sanctuary for your week away, or just provide peace of mind when the children are running around with the dog. Defying all but the most resolute escapees, our cottages with enclosed gardens will help to rein in adventurous legs. Sit back and relax and watch as your loved ones play in a private idyll. Our luxury cottages provide a real home-from-home on the Isle of Wight.

Isle of Wight Cottages that have an Enclosed Garden

Combining home comforts with modern luxuries, our self-catering holiday cottages on the Isle of Wight provide the perfect base to explore the island. Handpicked and personally inspected, each of our properties is of the finest quality around. At Classic Cottages, we want your whole experience to be as relaxed and easy as possible, and will always go the extra mile to ensure your holiday is the best it can be.