Wool Holiday Cottages

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We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Wool Holiday Cottages

REFINE SEARCH

Your Wool, Dorset search returned 133 cottages

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Map View
A brick house with black doors and windows a bench and potted plants outside at Meadow View Barn in Bere Regis
29
Bere Regis, Dorset, BH20
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Charming, modern barn located in the Dorset village of Bere Regis. WiFi. Close to shop and pub. Off-road parking. Courtyard garden. Wareham 6 miles. (Ref. 1000906)

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


for 7 nights $658

Last booked 2 days ago
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A wooden cabin with a fenced yard and a smaller shed behind surrounded by trees at Hill View Lilac Lodge in Wareham
29
Wareham, Dorset, BH20
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A contemporary single-storey lodge nestled on the outskirts of Wareham, Dorset. Open-plan. En-suite. Enclosed garden. Corfe Castle 5.6 miles; Poole 9.5 miles; Swanage 12.2 miles. (Ref. 1079216)

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


for 7 nights $961

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A cottage with a thatched roof and red door next to another house with a driveway and parked car at Cosynook Cottage in Winterborne Kingston
23
Winterborne Kingston, Dorset, DT11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

An attractive end-terrace cottage found in the peaceful Dorset village of Winterborne Kingston. Ideal for couples. Private parking. Pet friendly. Blandford Forum 6.5 miles; Poole 14.2 miles; Bournemouth 18.5 miles. (Ref. 1075037)

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


for 7 nights $621

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A brick house with six windows and a central door with plants on the pavement at Manor Farm House in Bere Regis
43
Bere Regis, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Manor Farm House is a charming Georgian abode with two woodburning stoves and accepting pets, located in the picturesque village of Bere Regis, Dorset. Wareham 7 miles; Dorchester 11.2 miles; Poole 12.4 miles. (Ref. 1158581)

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


for 7 nights $847

Last booked yesterday
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A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
43
Dorchester, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights $982

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A wooden house with large glass doors a hot tub a lawn and a patio area at The Barn in Lytchett Matravers
56
Lytchett Matravers, Dorset, BH16
  • Sleeps10
  • Bedrooms4
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A beautifully-presented, single-storey abode residing in Lytchett Matravers, Dorset. Near an AONB. Off-road parking. Hot tub. En-suite bedrooms. Poole 5.9 miles; Bournemouth 11.4 miles; Dorchester 18.7 miles. (Ref. 1084629)

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

  • 5% off - Fri 19th Dec to 31st Dec 2025


for 7 nights $2061

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An outdoor patio area with a wooden table and six wooden chairs in front of a modern concrete structure with large sliding glass doors at Standby Generator Bunker Ringstead near Weymouth
68
Ringstead near Weymouth, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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


for 7 nights $1317

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An outdoor patio with a hot tub wood siding on the house a table with chairs and an umbrella at Stag Cottage in Lytchett Matravers
47
Lytchett Matravers, Dorset, BH16
  • Sleeps6
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This stunning, two-bedroom abode is perched in Lytchett Matravers, Dorset. Off-road parking. Hot tub. En-suite bedrooms. Poole 5.9 miles; Bournemouth 11.4 miles; Dorchester 18.7 miles. (Ref. 1084628)

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

  • 10% off - Fri 31st Oct to 18th Dec 2025

  • 5% off - Fri 19th Dec to 31st Dec 2025


for 7 nights $1041

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An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
33
Ringstead, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)

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


for 7 nights $1041

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The exterior of a house with white walls and wooden paneling a patio area with a table umbrella and chairs at Whitegates Lodge in Osmington
15
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Link detached modern annex lodge in the Dorset Coastal village of Osmington. Wifi. Parking for two cars. Short drive to Weymouth. (Ref. 994794)

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


for 7 nights $678

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A stone and brick cottage with a thatched roof surrounded by plants and flowers at Forge Cottage in West Lulworth
30
West Lulworth, Dorset, BH20
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Short description: Ideal stay for walkers and ramblers to explore the Jurassic Coast. Local pubs and restaurants. Wifi. Off road parking. (Ref. 994203)

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


for 7 nights $973

Last booked yesterday
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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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


for 7 nights $1009

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A gravel driveway in front of a building with large windows and a slate roof at The Courtyard - Hilltop Barn in Winterborne Zelston near Wareham
41
Winterborne Zelston near Wareham, Dorset, DT11
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A beautiful detached barn conversion situated in the lovely Dorset area of Winterborne Zelston near Wareham and Wimborne Minster. Underfloor heating. Countryside views. Character. Wareham 8.3 miles; Wimborne Minster 8.7 miles; Poole 11.3 miles. (Ref. 1058078)

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


for 7 nights $1010

Last booked 2 days ago
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A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
25
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)

  • Wi-fi
  • Dishwasher


for 7 nights $658

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A brick house with a balcony and garden with bushes and small trees at Henbury Hide in Corfe Mullen
34
Corfe Mullen, Dorset, BH21
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A well-furnished, upside-down cottage in Corfe Mullen, Dorset. Upside-down living. Balcony and decking upstairs. Heart of Corfe Mullen. Ref 962749. (Ref. 962749)

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


for 7 nights $603

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Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
39
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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


for 7 nights $830

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A stone cottage with a thatched roof next to a road with green planters under windows at Ivy Cottage in West Lulworth
27
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Lovely thatched Grade II listed cottage for a family or friends. Welcomes two dogs. Original beams. Beach 1 mile. Pub 5 min. Seasonal shop 10 min. (Ref. 994302)

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


for 7 nights $977

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A house with windows and a garden at June Cottage in Wool
35
Wool, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

June Cottage is a lovely cottage situated on the outskirts of Wool in Dorset, allowing pets and is well-situated to nearby attractions and amenities. East Lulworth 4.3 miles; Wareham 6.3 miles; Weymouth 12.9 miles. (Ref. 1181945)

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


for 7 nights $733

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A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
44
Sutton Poyntz, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights $697

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A stone and brick house with a slate roof and arched doorway by a hedge at St Mary's Chapel in West Lulworth
25
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Located in the coastal village of West Lulworth is this stunning converted chapel. Stylish and contemporary interior. WiFi. Woodburning stove. Wareham 8.9 miles; Dorchester 12.7 miles; Weymouth 20.7 miles. (Ref. 1055781)

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


for 7 nights $1501

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Map View

Please find below a selection of self catering holiday cottages to rent in or near Wool.