Rural Retreats on the Isle of Wight

Rural Retreats on the Isle of Wight

Fall in love with our selection of rural retreats on the Isle of Wight. All of our self catering cottages are carefully chosen and personally inspected so that you can enjoy the best of the best. Be it a big cottage equipped for a large group or cosy retreat for two, you will be sure to find something that hits the spot. Browse our selection and let your imagination run wild.  Read more

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

Discover our selection of rural cottages on the Isle of Wight

Grace Cottage is a 1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £560

Grace Cottage

4209

1 bedroom holiday cottage close to the sea near Ventnor, Isle of Wight


This gorgeous barn conversion is set within the grounds of the stunning North Grounds Farm, just outside the village of Chale Green on the southern side of the Island. For the envi...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £560

Escape Away is a 2 bedroom self catering cottage near the beach in Freshwater.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £714 *

Escape Away

5612

2 bedroom self catering cottage near the beach in Freshwater.


Close to the beach, a short drive from pretty Yarmouth and not far from the iconic Needles, Escape Away is the perfect luxury retreat to base yourself for a peaceful and relaxing h...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £714 *

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 £714 *

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 £714 *

Bay View is a 2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £748 *

Bay View

3902

2 bedroom, rural holiday apartment near the beach in Freshwater, Isle of Wight


Perched above the stunning Freshwater Bay, this elegant contemporary apartment offers breathtaking views of the scenic coastline and the ultimate spot for refreshing seaside dips. ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £748 *

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 £763 *

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 £763 *

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 £594

The Cattle Byre

4535

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


The Cattle Byre has accommodation for three guests across two bedrooms, a double and a small single. It has two private outdoor seating areas, the rear enclosed garden can only be ...

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

7 nights from £594

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 £460

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 £460

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 £606

The Dairy

4536

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


The Dairy is the largest of all four barns and is closest to The Cattle Byre. It has a spacious kitchen and dining area making it a social space for the family to gather and make p...

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

7 nights from £606

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

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 £609

The Stables

4537

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


The Stables is light and airy throughout with two bedrooms, a king-size double and a twin. The open plan living-room with kitchen and dining areas is warm and inviting, with doors ...

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

7 nights from £609

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 £609

The Pigsty

4538

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


The Pigsty is a detached barn with parking for two cars and two private seating areas along with a spacious communal area. There are two bedrooms, a double and a twin, each bea...

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

7 nights from £609

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The Isle of Wight, the UK's dinosaur capital, is an island with soaring chalky white cliffs and raw, devastatingly beautiful coastline. Known for its famous fossil hunting opportunities and seaside towns with brightly-coloured beach huts and seafront promenades, the Isle of Wight is a wonderful place for a rural retreat.

Whether you are looking for a cosy 1 bedroom cottage or sea view homes perfect for big groups, the choices are endless for an idyllic countryside getaway. Because we understand the importance of high quality accommodation, all of our self catering cottages meet exacting standards. All you have to do is choose your dream cottage and the rest will be taken care of for you.