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.  

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 66 Isle of Wight cottages with enclosed gardens

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

Price per week £405 - £1071

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

Price per week £413 - £898

3 bedroom self catering cottage in Newport, Isle of Wight


Located in the centre of the Island on the outskirts of the town of Newport, this is perfectly located to explore different places on the Isle of Wight. In the colder months, wrap ...

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

Price per week £495 - £1415

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


This modern and bright bungalow with a south-facing garden is perfect for a family holiday and as it has a fully-enclosed rear garden, why not bring your four-legged friends? Sleep...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £384 - £850

3 bedroom, dog friendly apartment near the beach in Seaview, Isle of Wight.


1 Astra House is a comfortable, light and bright ground floor apartment set within a charming Victorian property in Seaview. Featuring an open plan layout, the dining-area, kitchen...

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

Price per week £398 - £895

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

Price per week £399 - £860

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

3 bedroom self catering cottage near the beach in Shanklin.


25 Palmerston Road is a bright, cheerfully decorated, family home and is one of our most popular properties. This property is a real find for a family looking for a home both close...

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

Price per week £427 - £920

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


Set in the delightful sailing village of Seaview, Blackberries is a pretty, refurbished cottage which offers a peaceful escape for families, small groups or couples alike. Comforta...

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

Price per week £436 - £969

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

Price per week £451 - £990

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


The wow factor at 4 Commodores Court is the location; perched directly opposite the beach it has stunning views of the Solent from the front, and delightful rural and lakeside view...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £461 - £930

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