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Isle of Wight Holiday Cottages

202 properties found

A courtyard with brick paving surrounded by buildings with brick and cream walls at 2 The Stables in Ryde

2 The Stables

Ryde, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£342

An outdoor seating area with two chairs a wooden bench a fire pit a low table with cushions and wine glasses under string lights at The Old Brewhouse & Piggery in Ningwood near Shalfleet

The Old Brewhouse & Piggery

Ningwood near Shalfleet, Isle of Wight

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£499

A brick building with a tiled roof potted plants and a street lamp on a paved courtyard at 3 The Stables in Ryde

3 The Stables

Ryde, Isle of Wight

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£325

A house with thatched roof and stone wall at Sheepwash Barn in Freshwater

Sheepwash Barn

Freshwater, Isle of Wight

3 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£570

A wooden cabin with a slate roof a patio with table and chairs and two potted plants on a grassy lawn at The Springs in Ashey near Brading and Ryde

The Springs

Ashey near Brading and Ryde, Isle of Wight

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£447

A stone cottage with a tiled roof and garden table under a tree at Lisle Combe Cottage in St Lawrence near Ventnor

Lisle Combe Cottage

St. Lawrence near Ventnor, Isle of Wight

6 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£450

Woodsmoke Cottage

Woodsmoke Cottage

Shorwell, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£856

A stone house with a gravel driveway and trimmed hedges under a blue sky at The Old Dairy in Gatcombe

The Old Dairy

Gatcombe, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£442

A wooden sign with the word westmount on a red brick wall next to a red door at Westmount in Ryde

Westmount

Ryde, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£268

An outdoor view of a house with flowers and fence at The Old Post Office St. Lawrence near Ventnor

The Old Post Office

St. Lawrence near Ventnor, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£552

A living room with a bicycle and wood stove at tbc

Hearth Cottage

Shorwell, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£856

A garden with outdoor seating and dining furniture in front of a brick house at 4 The Nab House in Bembridge

4 The Nab House

Bembridge, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£503

An outdoor area with a wooden building and patio furniture at Farmhouse Sleeps 5 Near Alton Towers Peak District Shorwell

Poachers Hut

Shorwell, Isle of Wight

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£856

A living room with sofas and cushions a patterned rug and a dining area with chairs and table at Sandy Cottage in Sandown

Sandy Cottage

Sandown, Isle of Wight

4 Guests
2 Beds
Pet Friendly
Wifi

for 7 nights

From

£479

The exterior of a stone cottage with white doors and windows and a tiled courtyard entrance with shrubs at Dairy Cottage in Gatcombe

Dairy Cottage

Gatcombe, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£569

A street with a cream colored building beside the beach and sea in the background at Seaside in Ventnor

Seaside

Ventnor, Isle of Wight

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£317

A house with a balcony and multiple windows at 6 Priory in Shanklin

6 Priory

Shanklin, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£407

The exterior of a stone house with a blue door and white framed windows and a small paved area with steps and potted plants at 4 The Old Post Office Mews Brading

4 The Old Post Office Mews

Brading, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£396

A garden with a brick path leading to a building surrounded by plants and flowers at 1 The Stables in Ryde

1 The Stables

Ryde, Isle of Wight

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£341

A deck with two striped lounge chairs and a small round table with a bottle and wine glasses outside a mobile home at The Retreat Near Shorwell

Rowborough House

Near Shorwell, Isle of Wight

4 Guests
3 Beds
No pets
Wifi

for 7 nights

From

£408

Found just off the South Coast of England are these Isle of Wight cottages the perfect choice for your next staycation. The Isle of Wight combines the best of a countryside escape with a fantastic beach holiday, there’s no limit to what you can get up to from these holiday cottages on the Isle of Wight! 

Why Holiday Cottages Isle of Wight? 

Home to a beautiful heritage coastline and a designated national landscape, the Isle of Wight makes for a wonderful place to spend your next break. Dotted with quaint towns and villages across its vast countryside, as well as tonnes of amazing attractions and landmarks like Carisbrooke Castle, Osborne House and unique attractions like the Isle of Wight Donkey Sanctuary, you won’t run out of things to see and do! 

What’s best is that staying in one of these Isle of Wight cottages places you no more than a short drive away from it all. Providing you with all the amenities and creature comforts of home, as well as plenty of space to unwind and relax, they make for the perfect bases to explore this wonderful island during your stay!

For more ideas on what to get up to during your Isle of Wight holiday, check out our Isle of Wight Travel Guide » 

Places to visit during Isle of Wight Holidays

With so much to see, do and discover across the island, you’ll have no problems planning your adventures from your Isle of Wight accommodation!  

One place we’d recommend visiting for a day trip is the town of Ryde, found on the island’s northern shores. Known for being the largest town on the island and famously referenced in the hit Beatles song “Ticket to Ride”, this wonderful town is packed full of independent shops, old-world pubs, cafés, bars and restaurants for you to enjoy. Here, you’ll also find the popular Ryde Beach, as well as a host of great attractions next to it like the Ryde Superbowl and the Peter Pan Funfair... perfect if you’re visiting with the family! 

Another fantastic place to visit during Isle of Wight holidays is Sandown, found on the island’s southern shores. Home to a bustling pier that stretches across Sandown Beach where you’ll find a great bar, café and ice cream kiosk, here you’ll also find some great attractions to explore such as Dinosaur Isle and the beautiful Battery Gardens that offer impeccable views over the English Channel. 

Other Popular Destinations to Visit during Isle of Wight Holidays:

Colwell Bay 

Cowes 

Freshwater 

Godshill 

Newport 

Shanklin 

Ventnor

Wootton Bridge

Yarmouth 

You can also check out the full list of Isle of Wight destinations »

Types of Isle of Wight Holidays

Book your next adventure today by choosing one of these Isle of Wight cottages! 

As well as these holiday cottages on the Isle of Wight, there are still plenty more properties to take a look at. Enjoy a holiday with your pooch at one of these dog-friendly Isle of Wight cottages or treat yourself to something extra special with these luxury Isle of Wight cottages.  

Make the most of the countryside by booking a stay in one of these lodges and log cabins on the Isle of Wight. If you’re looking for something unusual, try these glamping breaks on the Isle of Wight. Families will also be in their element thanks to these holiday parks on the Isle of Wight.

Or, perhaps you're heading to the island's famous festival? If so, then you should definitely check out these places to stay near the Isle of Wight Festival!

If you’re planning a spontaneous getaway then these last-minute breaks on the Isle of Wight or these Isle of Wight short breaks, might be helpful. Don’t worry if you still haven’t found what you’re looking for as there are plenty of other cottages in the South East to choose from.

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