Isle of Wight Holiday Cottages
British Travel Award Winners!
We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.
Popular property types
See all properties
Pet friendly
91 properties
Properties with hot tubs
19 properties
Luxury
12 properties
Log cabins
20 properties
Properties with character
78 properties
Remote
8 properties
Your Isle of Wight search returned 201 cottages
- Sleeps2
- Bedrooms1
- PetsNo
An idyllic renovated cottage resting near Shalfleet on the Isle of Wight. Woodburning stove. Smart TV. Superfast WiFi. Close to beach. Yarmouth 2.8 miles; Freshwater 5.7 miles; Newport 7.2 miles; Cowes 9.9 miles. (Ref. 980661)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from €663
- Sleeps6
- Bedrooms3
- PetsNo
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 €814
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps6
- Bedrooms3
- PetsNo
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 €1275
Offer
- Sleeps8
- Bedrooms4
- PetsYes
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
-
€713 off - Sat 3rd May to 17th May 2025
7 nights from €930
- Sleeps4
- Bedrooms2
- PetsYes
This charming two-bedroom holiday home rests in Sandown, Isle of Wight. In an AONB. Pet-friendly. Off-road parking. Enclosed garden. Shanklin 2.6 miles; Ryde 5.9 miles; Newport 8.9 miles; Cowes 13.4. (Ref. 1126551)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from €595
- Sleeps3
- Bedrooms2
- PetsYes
Superb thatched 17th century cottage in hamlet of Middleton, near Freshwater. Single-storey accommodation. Pet-friendly. Ideal for a couple. Freshwater 0.5 miles. (Ref. 951450)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Washing machine
7 nights from €641
- Sleeps5
- Bedrooms3
- PetsYes
A wonderful property with a lot of character, St. Michael’s House is the perfect property for families or a group of friends. Dog-friendly. Near the coast. Bembridge 2.3 miles. (Ref. 1000597)
- Wi-fi
- Washing machine
7 nights from €569
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps6
- Bedrooms3
- PetsNo
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 €670
- Sleeps6
- Bedrooms3
- PetsYes
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 €718
- Sleeps7
- Bedrooms4
- PetsYes
Wicking is a gorgeous detached holiday house located in the beautiful seaside resort of Ventnor, Isle of Wight. Woodburning stove. Close to beach and amenities. Pizza oven. Newport 10.5 miles; Cowes 15 miles. (Ref. 1046702)
- Wi-fi
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
- Games room
7 nights from €970
- Sleeps6
- Bedrooms3
- PetsNo
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 €556
- Sleeps8
- Bedrooms4
- PetsYes
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 €1399
- Sleeps4
- Bedrooms2
- PetsYes
A fantastic stone-built cottage resting on the outskirts of Wroxhall on the Isle of Wight. Enclosed garden. Breath-taking views. Pet-friendly. Ventnor 3.1 miles; Shanklin 4.2 miles. (Ref. 1080047)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €580
- Sleeps2
- Bedrooms1
- PetsYes
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 €342
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps6
- Bedrooms3
- PetsYes
Chantries is a delightful, detached cottage in the village of Bembridge, Isle of Wight. Open fire. Barbecue. Pet-friendly. Child-friendly. Near coast. Ryde 7.5 miles; Newport 11.7 miles; Cowes 16.2 miles; Yarmouth 21 miles. (Ref. 1158892)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €857
- Sleeps4
- Bedrooms2
- PetsNo
Marina View is a delightful, ground-floor apartment nestled near the sea in Cowes, Isle of Wight. Harbour views. Near amenities. Ground-floor living. Newport 4.9 miles; Ryde 11.3 miles; Shanklin 13.9 miles; Ventnor 15.2 miles; Freshwater 15.4 miles. (Ref. 1125801)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Sky TV
7 nights from €571
- Sleeps7
- Bedrooms4
- PetsYes
A striking chocolate box cottage tucked away in the village of Chale, on the Isle of Wight. Original features. Close to the coast. Off-road parking. Brighstone 5.6 miles; Shanklin 8.5 miles; Bembridge 14.4 miles. (Ref. 1052289)
- Wi-fi
- Off-road parking
- Electric vehicle charging
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €984
- Sleeps6
- Bedrooms3
- PetsNo
Wonderfully located barn conversion cottage in the small hamlet of Gatcombe. Well-equipped, comfortable accommodation. Enclosed patio with furniture. Stunning walks and mountain biking from cottage. Newport 4 miles. (Ref. 903663)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €663
- Sleeps8
- Bedrooms4
- PetsNo
This superb stone cottage is based in Luccombe, Isle of Wight. WiFi. Off-road parking. Enclosed garden. Newport 10 miles; Cowes 15 miles. (Ref. 991785)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
7 nights from €1867
- Sleeps8
- Bedrooms4
- PetsNo
This charming detached house rests in the heart of Sandown, on the Isle of Wight. Electric fire. Enclosed garden. Shanklin 1.4 miles; Ventnor 5.6 miles. (Ref. 1020856)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from €767
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:
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.