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Isle of Wight Holiday Cottages

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Your Isle of Wight search returned 206 cottages

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  • Sleeps12
  • Bedrooms4
  • PetsYes
  • Sykes rating

Milston is a lovely, dog-friendly house situated close to a beach near Chale, Isle of Wight, boasting a woodburning stove, enclosed garden, and sea views. Ventnor 7.2 miles; Shanklin 8.5 miles. (Ref. 1171872)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • 10% off - Tue 1st Jul to 8th Jul 2025

7 nights from £1016

  • Sleeps12
  • Bedrooms4
  • PetsYes
  • Sykes rating

Tall Timbers, a lovely coastal cottage set in the Victorian town of Ventnor in Isle of Wight, enjoying a pet-friendly policy and a short walk to a beach. Newport 11.5 miles; Cowes 16 miles. (Ref. 1163988)

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

7 nights from £870

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

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 £554

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

A smart, shepherd's hut based on the edge of Seaview, Isle of Wight. Woodburning stove. Beach nearby. Romantic dwelling. Sandown 5.4 miles; Newport 8.9 miles. (Ref. 1083797)

  • Off-road parking
  • Ground floor bedroom

7 nights from £418

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

The Granary is a lovely, converted granary that, ideal for couples, resting near the lovely village of Freshwater on the Isle of Wight with a hot tub. Yarmouth 1.5 miles; Cowes 16.3 miles; Fishbourne 18 miles; Ryde 20 miles. (Ref. 1173924)

  • Wi-fi
  • Off-road parking
  • Hot Tub

7 nights from £392

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A delightful studio-style annexe resting in Bembridge, Isle of Wight. Contemporary. Close to amenities and the beach. Off-road parking. Romantic. Ryde 7.5 miles; Newport 10.5 miles; Cowes 15.4 miles; Yarmouth 20.5 miles. (Ref. 1077923)

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

7 nights from £349

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

One of a group of three properties in beautiful countryside location. All ground floor. One double bedroom with en-suite wet room. Beach, shops and bars close by. Ryde 2 miles. (Ref. 12935)

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

7 nights from £354

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Stylish, detached, Scandinavian-style timber lodge in tranquil setting near Ryde, Isle of Wight. Use of heated outdoor swimming pool. Rural setting. Parking. WiFi. Ryde, 3.1 miles; Sandown 3.7 miles; Ventor 9.2 miles. (Ref. 2906)

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

7 nights from £416

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

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 £572

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

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 £843

Last booked yesterday
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  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Frosthill Cottage is a spacious cottage resting in the town of Carisbrooke, Isle of Weight. Historic sites. Off-road parking. Woodburning stove. Newport 1.8 miles; Cowes 7.1 miles; Yarmouth 10.1 miles. (Ref. 1140820)

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

7 nights from £698

  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.3

    Good

  • Sykes rating

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 £831

Last booked 2 days ago
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  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

An attached coach house conversion in the village of Wroxall in the Isle of Wight. On Appuldurcombe Estate. Pet-friendly. Surrounding woodland. (Ref. 960233)

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

7 nights from £563

7 nights from £415

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Pierpont D1 is a pleasant single-storey holiday home settled on The West Bay Club in Norton near Yarmouth, on the Isle of Wight with on-site facilities. Newport 10.7 miles; Ryde 17.4 miles. (Ref. 1169089)

  • Wi-fi
  • Ground floor bedroom

7 nights from £348

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Delaware M5, a lovely, terrace cottage located in the quaint town of Yarmouth in Isle of Wight. Near coast. Near pub. Open plan. Family-friendly. Newport 11.1 miles; Ryde 18 miles. (Ref. 1155203)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £376

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Cape A6 is a semi-detached, seingle-storey holiday home located in the Norton near the town of Freshwater in the Isle of Wight with private decking. Yarmouth 1.2 miles; Cowes 13.9 miles; Fishbourne 15.6 miles; Ryde 17.6 miles. (Ref. 1171473)

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

7 nights from £348

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

A superb two-bedroom eco lodge resting in Pondwell near Seaview, Isle of Wight. Open-plan. Country views. Near a beach. Hot tub. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1081343)

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

7 nights from £604

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Muscat is a delightful two-bedroom eco lodge resting in Pondwell near Seaview, Isle of Wight. Open-plan. Country views. Near a beach. Pet-free. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1083796)

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

7 nights from £580

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This contemporary, two-bedroom eco lodge rests in Pondwell near Seaview, Isle of Wight. Open-plan. Country views. Near a beach. Hot tub. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1083794)

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

7 nights from £570

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.