Summer Holiday Cottages on the Isle of Wight

Summer Holiday Cottages on the Isle of Wight

A summer on the Isle of Wight in a Classic cottage is pretty hard to beat when it comes to finding your British summer holiday away. So why not explore all that the Isle of Wight has to offer, and in the evening return to your own private paradise. For an unforgettable summer, we have 106 holiday homes available for you to rent. Read more

Escape for a week or two by hopping on a ferry and heading to the island. It instantly feels like you're 'getting away from it all' when you travel by boat! Explore the incredible coastline, dip in the sea for a swim or two and explore all corners the Isle of Wight has to offer for a perfect self catering holiday this summer. 

Whatever you are looking for in a summer break, choose the flexibility a holiday cottage on the Isle of Wight will give you. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

106 self-catering cottages for the summer holidays on the Isle of Wight

Oak Tree Cottage is a 3 bedroom self catering cottage with sea views in Seaview, Isle of Wight
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1332

Oak Tree Cottage

4212

3 bedroom self catering cottage with sea views in Seaview, Isle of Wight


With a stunning spacious sea facing balcony, Oak Tree Cottage is in a superb location just steps from the beach and a short walk along the seafront into Seaview Village. An outdoor...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1332

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 £724

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 £724

1 St Josephs is a 2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £908

1 St Josephs

4183

2 bedroom self catering apartment with sea views in Ventnor, Isle of Wight


With one of the best views on the Isle of Wight, 1 St Josephs is a superb ground floor apartment beautifully decorated throughout. The property has a large patio area spanning two ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £908

61 Solent View is a 4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1614

61 Solent View

4078

4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight


On the outskirts of Seaview and within a few minutes' walk from Seagrove Bay, take in the stunning sea views from not one but two balconies. 61 Solent View is a wonderful holiday h...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1614

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 £1216

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 £1216

The New House is a 4 bedroom self catering cottage in Godshill, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1507

The New House

4025

4 bedroom self catering cottage in Godshill, Isle of Wight


Nestled in the heart of the chocolate-box village of Godshill, this detached house has beautiful secluded gardens to the rear and everything the village can offer within a few minu...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1507

St Albans House is a 4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1203

St Albans House

3980

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1203

Flackstead is a 3 bedroom self catering cottage near the beach in Brook, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £3021

Flackstead

3913

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


Flackstead is a unique eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of co...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £3021

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

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 £1170

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 £1170

Solent Heights is a 5 bedroom self catering cottage near the beach in Cowes, Isle of Wight
  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2774

Solent Heights

3946

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


A beautifully designed, contemporary home in the popular sailing town of Cowes, Solent Heights boasts sea views and quality finishes throughout. Set over four floors - including ba...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £2774

Loading more