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Isle of Wight Short Breaks

Your Isle of Wight search returned 167 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps16
  • Bedrooms6
  • Pet FriendlyYes

    4.7

    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)

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


for 3 nights From £1364

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From £482

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

A well-presented, two-bedroom eco lodge based in Pondwell near Seaview, Isle of Wight. Country views. Beach nearby. Hot tub. Sandown 5.4 miles; Newport 9.1 miles. (Ref. 1081444)

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


for 3 nights From £592

  • Sleeps12
  • Bedrooms4
  • Pet FriendlyYes

    5.0

    Perfect

  • 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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From £809

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

This delightful stone cottage is based in Totland Bay, on the Isle of Wight. Open-plan living. Woodburner. Country views. Freshwater 1 mile; Yarmouth 3 miles. (Ref. 972940)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 26th Jun to 31st Dec 2026


for 3 nights From £635

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

5A Castle Street, a nicely-presented holiday home is located in the lovely seaside town of Ryde on the Isle of Wight. Three-storeys. Enclosed courtyard. Sandown 6 miles; Newport 7.5 miles. (Ref. 1148236)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 3 nights From £376

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Ground floor barn conversion. One of a group of three with spectacular views. Wheelchair access. Beach, shops and pubs nearby. Ryde 2 miles. (Ref. 12934)

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


for 3 nights From £323

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5

    Outstanding

  • Sykes rating

Cava is a wonderfully-presented eco lodge nestled 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. 1083793)

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


for 3 nights From £592

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A spacious, semi-rural and semi-detached holiday cottage with tasteful decor and a pretty, traditional cottage garden. Between two beautiful beaches. (Ref. 948494)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From £376

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.8

    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)

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


for 3 nights From £255

  • Sleeps4
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From £477

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Hayloft is a first-floor, pet-friendly apartment situated in Bonchurch near the seaside town of Ventnor, Isle of Wight, and is set just a short walk from the beach. Newport 12.1 miles; Cowes 16.5 miles. (Ref. 1167864)

  • Pets go free
  • Off-road parking
  • Washing machine
  • Baby-friendly


for 3 nights From £380

Last booked yesterday
See more details
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

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)

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


for 3 nights From £720

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyYes

    4.6

    Outstanding

  • 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)

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


for 3 nights From £491

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyYes

    4.8

    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)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From £622

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Stable Cottage is a charming and historical, pet-friendly cottage situated on the outskirts of the pretty village of Wroxall on the Isle of Wight. Ventnor 3 miles; Shanklin 4.1 miles (Ref. 960240)

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


for 3 nights From £422

Last booked yesterday
See more details