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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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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming holiday home nested in the countryside near Meonstoke, Hampshire. Woodburning stove. Dog-friendly. In South Downs National Park. New Alresford 10.1 miles; Winchester 12.1 miles; Portsmouth 15.4 miles (Ref. 1113322)

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

7 nights from £1105

Last booked 2 days ago
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  • 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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  • Sleeps15
  • Bedrooms8
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A grand, eight-bedroom home resting in Meonstoke, Hampshire. Countryside views. In AONB. Pet-friendly. Large. Open fire. Close to amenities. Droxford 1.7 miles; New Alresford 11.6 miles. (Ref. 1124828)

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

7 nights from £2223

Last booked yesterday
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  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A grand, five-bedroom home located on the outskirts of Ringwood, Hampshire. In National Park. Games room. Hot tub. Tennis court. Large. Pet-friendly. Open fire. Bournemouth 13.3 miles; Poole 18.3 miles. (Ref. 1134272)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £2723

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A contemporary three-storey cottage resting in Bursledon, Hampshire. Character features. Hot tub. Stylish. Games room. Close to amenities. Southampton 5.9 miles; Gosport 11.8 miles; Portsmouth 15.3 miles. (Ref. 1108240)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £1344

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This lovely, detached property rests in Highwood near Ringwood, Hampshire. In a National Park. Pet-friendly. Off-road parking. Woodburning stove. Close to amenities. Bournemouth 13.9 miles; Poole 18.9 miles (Ref. 1124526)

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

7 nights from £1165

  • 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

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Little Barn is a stunning holiday home tucked away in the rural outskirts of Stockbridge, a charming town in Hampshire. Pet-friendly. Smart TV. Dishwasher. Winchester 10.1 miles; Salisbury 15.9 miles; Southampton 17.3 miles. (Ref. 1136243)

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

7 nights from £738

Last booked 2 days ago
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  • 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

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A well-presented single-storey annexe resting in Ryde, Isle of Wight. Ground-floor living. Dog-friendly. WiFi. Sandown 4.7 miles; Newport 8.5 miles. (Ref. 1073801)

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

7 nights from £290

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A beautiful cottage located in the heart of Brockenhurst in Hampshire. Wonderful enclosed garden. Homely interior. Perfect for families. Lyndhurst 3.9 miles; Cadnam 7.5 miles. (Ref. 971907)

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

7 nights from £684

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A delightful three-bedroom semi-detached house resting in Totland Bay on the Isle of Wight. Dog-friendly. Off-road parking. Near a beach. Freshwater 1 miles; Yarmouth 2.8 miles. (Ref. 1043546)

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

7 nights from £514

  • 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

  • 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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  • Sleeps16
  • Bedrooms6
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Burwyns is a wonderful six-bedroom holiday home resting in Ventnor, Isle of Wight. Close to amenities. Pet-friendly. Near Isle of Wight AONB. Sea views. Newport 11.5 miles; Cowes 16 miles. (Ref. 1143991)

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

7 nights from £1410

  • 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

  • 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

    4.8

    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

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This spacious coach house is situated in Whitsbury near Fordingbridge. Large garden. Wheelchair friendly. Woodburning stove. Fordingbridge 3.2 miles; Salisbury 10.4 miles; Bournemouth 21 miles. (Ref. 1041121)

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

7 nights from £695

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A well-presented chalet nestled in the New Forest. Open-plan living. Off-road parking. Salisbury 13.1 miles. (Ref. 1137480)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £627

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.