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

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Your Wool, Dorset search returned 134 cottages

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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
67
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 £1001

Last booked yesterday
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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 £500

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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. Inglenook fireplace and 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 £701

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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 £654

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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 £693

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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
40
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


for 7 nights £828

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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 £521

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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 £641

Last booked yesterday
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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
49
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


for 7 nights £1558

Last booked yesterday
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A fenced swimming pool with chairs and lawn in front of a brick and wood house at Manor Farm Barn in Dewlish
42
Dewlish, Dorset, DT2
  • Sleeps15
  • Bedrooms8
  • PetsYes

    4.8★

    Outstanding

  • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. Dog-friendly. Off-road parking. Shared outdoor heated pool. Dorchester 7 miles. (Ref. 1003646)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

  • £50 off - Sat 18th Oct to 25th Oct 2025


for 7 nights £2348

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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 £458

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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 £641

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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 £472

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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
33
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 £747

Last booked 2 days ago
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A stone cottage with a thatched roof near the coast with grass and gravel paths at Pitt Cottage Ringstead
30
Ringstead, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Large kitchen diner. Beautiful rural location. Short walk to the sea. Wi-Fi. In the heart of the Jurassic coastline. Picture postcard thatched cottage. (Ref. 994553)

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


for 7 nights £940

Last booked 2 days ago
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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 £636

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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 £1142

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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 £515

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A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
36
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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


for 7 nights £714

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A living room with a brown sectional sofa armchair and round coffee table near a sliding door at Waterston Cottage in West Lulworth
42
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

This beautiful three-bedroom property resides in West Lulworth, Dorset. Off-road parking. In an AONB. En-suite bedrooms. Close to amenities and a beach. Wareham 8.8 miles; Weymouth 15.3 miles. (Ref. 1126738)

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


for 7 nights £781

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Map View

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