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

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. 

Isle of Wight Ferry Booking With 200 ferries daily, our hassle free booking service makes your trip to the island plain sailing

We have 62 Isle of Wight cottages with enclosed gardens

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £395

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


A really lovely little bungalow, holding true to its seaside location with a nautical feel to the interior styling, Spinnakers is situated on a small private estate within walking ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £395

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £411

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


Venice Lodge is a Georgian cottage located in a quiet residential area of the popular seaside town of Ryde. This is a unique house that you will not soon forget. If you long for th...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £411

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £514.20 £411.36

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £450

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


Tucked away down a quiet road leading to Fort Victoria Country Park on the outskirts of Yarmouth, Highgate is a superb holiday destination. Laid over one floor this property provid...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £450

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  • 15% off

    6 Apr 2019 - 13 Apr 2019

    £575.03 £488.77

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £298

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


A Victorian property set on a quiet road and yards from the beach. Oaks is a well-equipped property, decorated to a high standard and perfect for families with open plan seating an...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £298

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  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £372.74 £298.19

Need more time? Reserve any cottage for up to 24 hours before booking.

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

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


A deceptively spacious semi-detached Victorian property, Red House has a lovely large kitchen with both a breakfast-bar and a separate dining-area from which the enclosed garden ca...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £317

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  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £521.12 £416.80

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £414

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


The location of 40 Trelawny Way, on a quiet residential road in Bembridge, belies its extravagant interior. For those looking for a family home with an interior decorated with arti...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £414

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  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £516.97 £413.58

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

3 bedroom self catering cottage near the beach in Brook.


September Cottage is an excellent, family-friendly holiday home with an expansive, attractive kitchen and good-sized kitchen, sitting and dining areas. It's easy to imagine curling...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £421

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

7 nights from £400

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 £400

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £407

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


30 Seaview Bay is a lovely three bedroom apartment set over two levels, offering sea views from the master bedroom balcony. Doors from the sitting-room lead to a decked area and pr...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £407

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £424

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


East Gull Sands is an attached, comfortably furnished, beachfront holiday home in Seaview. Sitting right opposite the beach this property has sea views from the upstairs double bed...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £424

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  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £529.64 £423.72

Choose from our exclusive collection at the best prices with real time availability.

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