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Isle of Wight Holiday Cottages

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Your Isle of Wight & Hampshire search returned 323 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Garstons Barn is a lovely, three-bedroom barn conversion resting in Gatcombe near Newport, Isle Of Wight. In an AONB. Countryside views. Open-plan. Off-road parking. Cowes 9.5 miles; Ryde 10.9 miles; Yarmouth 12.3 miles. (Ref. 1133914)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £555

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Freshly decorated bungalow in the Dorset town of Highcliffe. En-suite. Dog-friendly. Beach 3 minute walk. (Ref. 973182)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £560

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A characterful farm building conversion resting in East Dean near West Tytherley, Hampshire. EV charging point. Near National Park. Riverside views. Family-friendly. Lockerley 1.5 miles; Salisbury 11.1 miles; Andover 16.5 miles; Southampton 16.5 miles. (Ref. 1119639)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £709

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

This lovely detached cottage is set in the heart of Bembridge, Isle of Wight. Off-road parking. Hot tub. En-suite. Ryde 7 miles; Newport 11 miles. (Ref. 998289)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine

7 nights from £629

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.2

    Good

  • Sykes rating

Luxurious, detached house in Netley Abbey near Southampton. Private, indoor heated swimming pool. En-suite facilities. Mezzanine social space with a bar. Wooded garden and lake. Southampton 4 miles. (Ref. 920526)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV
  • £1198 off - Sat 22nd Feb to 1st Mar 2025

  • £641 off - Sat 15th Mar to 22nd Mar 2025

  • £696 off - Sat 22nd Mar to 29th Mar 2025

7 nights from £1501

  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A fabulous, Island Stone barn conversion on the Isle of Wight Coastal Path, near Ventnor. Private patio with spectacular coastal and farmland views. Beach 5 mins walk. Ventnor 1.5 miles. (Ref. 926288)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £630

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A contemporary four-bedroom holiday home resting in Christchurch, Dorset. Open-plan. Enclosed garden. Pet-friendly. Close to the beach. Milford on Sea 7.9 miles; Bournemouth 8.2 miles. (Ref. 1085727)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £1318

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A spectacular church conversion set in the village of Chale Green, Isle of Wight. Coastal setting. Grand interiors. Spacious accommodation. Open-plan living. Shanklin 8.2 miles; Newport 9.6 miles; Totland 12.4 miles. (Ref. 1066825)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £1074

  • Sleeps5
  • Bedrooms3
  • PetsNo
  • Sykes rating

A wonderful holiday home resting in Hartley Wintney in Hampshire. Off-road parking. En-suite bathroom. Enclosed rear garden. Close to local amenities. Hook 4 miles; Basingstoke 11.3 miles; Reading 14.1 miles. (Ref. 1115232)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £707

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Horseshoe Cottage is a delightful cottage settled into the countryside of Lockerley near West Tytherley, Hampshire. Countryside location. Close to a shop. West Tytherley 3.7 miles; Sailsbury 12.4 miles. (Ref. 1148219)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Thu 2nd Jan to 31st Mar 2025

7 nights from £618

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A charming, detached cottage overlooking St. Helen’s Green, Isle of Wight. Woodburning stove. Pet-friendly. WiFi. Bembridge 2.1 miles; Ryde 5.2 miles. (Ref. 1102680)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £607

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Compton Grange - A charming, detached country cottage, a short walk from Compton Bay beach, situated between the town of Freshwater and the village of Brook, Isle of Wight. Beautiful sea views. Secret garden. Off-road parking. Yarmouth 6 miles; Cowes 13.5 (Ref. 1088285)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Games room

7 nights from £1186

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This superb detached lodge is nestled in the pretty village of Chale, on the Isle of Wight, England. Woodburner. Open-plan. En-suite. Enclosed garden. Ventnor 6.5 miles. (Ref. 939717)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £480

Last booked today
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stunning first-floor, duplex apartment in Brockenhurst, New Forest, Hampshire. Off-road parking. Open-plan. Central location. Feature fireplaces. Lyndhurst 4 miles; Cadnam 7.6 miles; Southampton 13.3 miles. (Ref. 1102022)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £741

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A beautiful detached cottage resting in Bembridge, Isle of Wight. Enclosed garden. Off-road parking. Woodburning stove. Ryde 7.9 miles; Newport 12 miles; Cowes 16.5 miles. (Ref. 1066102)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £670

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

A fabulous four-bedroom cottage resting in Hayling Island, Hampshire. Contemporary. Child and pet-friendly. Annex. Families. Close to beach and amenities. Fleet 3.5 miles; Havant 6.8 miles; Emsworth 8.6 mile; Portsmouth 13.3 miles. (Ref. 1069926)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £916

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A charming property set in the village of Totland, on the scenic Isle of Wight. Off-road parking. Electric fire. Enclosed garden. Freshwater 0.9 miles; Yarmouth 2.7 miles. (Ref. 1128375)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £523

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A thoughtfully-decorated single-storey lodge resting in Milford on Sea, Hampshire. Lakeside views. Pet-friendly. Off-road parking. Near a National Park. Lymington 4.5 miles; Bournemouth 13.3 miles. (Ref. 1125841)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £612

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

This attractive, single-storey holiday home rests on the water's edge in Ryde on the Isle of Wight. Private dock. Spacious. Boat parking. Stunning views. Newport 5.1 miles; Sandown 8.8 miles. (Ref. 1135043)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • 10% off - Sat 1st Feb to 29th Mar 2025

7 nights from £797

  • Sleeps4
  • Bedrooms3
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

1 Star Cottages is a delightful, terraced cottage resting in Freshwater, Isle of Wight. Pet-friendly. Close to a shop, pub, and beach. Enclosed garden. Yarmouth 2.7 miles; Newport 11.7 miles. (Ref. 1149357)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £436

Last booked 2 days ago
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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 here, check out our Isle of Wight Travel Guide » 

Places to visit from Isle of Wight Cottages 

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 from these Isle of Wight holiday cottages 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 near Isle of Wight Holiday Cottages:

Colwell Bay 

Cowes 

Freshwater 

Godshill 

Newport 

Shanklin 

Ventnor 

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

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.