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Dorset Holiday Cottages

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Your Dorset search returned 1,025 cottages

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A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
17
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. Walking distance to town centre. Pub, shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994737)

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


for 7 nights $993

Last booked 5 hours ago
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A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Gas Fire in Lounge, WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $887

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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

    4.7★

    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

  • 10% off - Sat 21st Mar to 28th Mar 2026


for 7 nights $2868

Last booked 2 days ago
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The exterior of a yellow building with white window frames and a dark blue door in Lyme Regis
52
Lyme Regis, Dorset, DT7
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A spacious, double-fronted, Grade II listed historic townhouse with garden in the heart of Lyme Regis, a minute's walk from the sea. Charmouth 3.4 miles; Bridport 10.2 miles. (Ref. 1142151)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $2537

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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

  • 10% off - Fri 3rd Apr to 17th Apr 2026


for 7 nights $676

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An exterior view of a stone building with a wooden door and windows surrounded by gravel at The Barn in Chedington near Crewkerne
36
Chedington near Crewkerne, Dorset, DT8
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Charming single-storey, detached barn conversion. Working farm in Area of Outstanding Natural Beauty. Lovely walking country. Woodburning stove. Pub close by. Crewkerne 4 miles. (Ref. 915096)

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


for 7 nights $486

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An exterior view of Wren Cottage in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $605

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A garden with a tree a flower bed and a wooden picnic table outside a two story house at Molly's Place in Boscombe
34
Boscombe, Dorset, BH5
  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A lovely ground-floor maisonette apartment resting in Boscombe, Dorset. Close to amenities and the beach. Pet-friendly. Ground-floor living. Private driveway. Bournemouth 1.8 mile; Christchurch 2.8 miles; Poole 8 miles. (Ref. 1086302)

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

  • 5% off - Fri 27th Mar to 9th Apr 2026


for 7 nights $757

Last booked 1 hour ago
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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
59
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 $2016

Last booked yesterday
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Backyard with dining table and chairs on patio and grass lawn at Lightkeepers Cottage in Lyme Regis
28
Lyme Regis, Dorset, DT7
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

An outstanding family holiday home close to Lyme Regis in Dorset. Family-friendly. Well-presented. Spacious. WiFi. Open-plan. Lyme Regis 0.4 miles; Axminster 5.3 miles; Seaton 7.9 miles; Weymouth 28.6 miles. (Ref. 1106632)

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


for 7 nights $1558

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A white two-story house with a porch and multiple windows next to a small body of water with green bushes at River Lym Cottage in Lyme Regis
33
Lyme Regis, Dorset, DT7
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A beautifully-presented two bedroom cottage located on the banks of the in Lyme Regis, Dorset. Patio garden. Two bedrooms. Patio garden. Charmouth 3 miles; Axminster 5.4 miles. (Ref. 1122609)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights $953

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A balcony with a wooden dining table and chairs overlooking a harbor with boats and buildings at Venezuela West Bay
37
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A desirable second-floor apartment close to West Bay in the heart of Dorset. Flexible accommodation. Lift access. WiFi. Open-plan. Harbour Views. West Bay 0.1 miles; Bridport 2 miles; Seatown 5.3 miles; Lyme Regis 11.4 miles. (Ref. 1106615)

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


for 7 nights $1064

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An outdoor area with brick walls and pathways at The Cottage in Wimborne Minster
44
Wimborne Minster, Dorset, BH21
  • Sleeps6
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A delightful single-storey holiday home resting in Wimborne Minster, Dorset. Dog-friendly. Ground-floor living. Countryside. Near Cranborne Chase AONB. Poole 5.3 miles; Bournemouth 7.5 miles; Blandford Forum 12.3 miles. (Ref. 1111758)

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


for 7 nights $755

Last booked yesterday
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A dining and living area with a wooden table, clear chairs, gray sofas, and windows at 2 Woodville Lyme Regis
20
Lyme Regis, Dorset, DT7
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A first-floor Georgian apartment settled in Lyme Regis, Dorset. Sea views. Close to a beach. Family-friendly. Charmouth 3.1 miles; Seaton 7.7 miles; Devon 37 miles. (Ref. 1106036)

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


for 7 nights $1260

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Front exterior of a house with a black door two potted plants and pink flowers in a garden at 6 The Terrace Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)

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


for 7 nights $1280

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A living room with two black leather sofas, a wood-burning stove, a wooden coffee table, a floor lamp, a small TV on a wooden stand, and glass doors with orange curtains at The Old Cart Shed in Winterborne Stickland
37
Winterborne Stickland, Dorset, DT11
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Exceptional, spacious rural barn conversion. Very high standard of furnishings and equipment. Beamed ceilings. Woodburning stove. En-suite facilities. Lovely walks close by. Blandford Forum 4 miles. (Ref. 905897)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights $748

Last booked 4 hours ago
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Exterior of a white two-story house with a pitched roof and blue front door at The White Cottage in Weymouth
51
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A stunning, detached home resting in Weymouth, Dorset. Enclosed garden. Near beach. Pet-friendly. Dorchester 7 miles; Bridport 19.7 miles; Poole 30.9 miles. (Ref. 1022573)

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

  • 15% off - Mon 23rd Feb to 2nd Apr 2026


for 7 nights $1414

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A living room with a sofa and lamp at 1 Mill Green Court Lyme Regis
37
Lyme Regis, Dorset, DT7
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

1 Mill Green Court, a beautifully presented ground-floor apartment in Lyme Regis, near the seafront, riverside walks, vibrant shops, pubs, and restaurants. Charmouth 2.9 miles; Axminster 5.5 miles; Bridport 9.6 miles; Sidmouth 15.7 miles. (Ref. 1178651)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

  • 10% off - Wed 11th Mar to 26th Mar 2026


for 7 nights $724

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A two-story house with a pitched roof on Hillcrest Road with a 20 mph zone sign and plants in Wyke Regis
46
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A fabulous three-bedroom holiday home in Wyke Regis, Dorset. Pet-friendly. Sea views. Close to beach and amenities. Open-plan. Contemporary. Weymouth 2.2 miles; Dorchester 9.6 miles. (Ref. 1103441)

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


for 7 nights $958

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A stone house with red ivy covering part of the walls and a tiled roof at The Cheesehouse in Litton Cheney
40
Litton Cheney, Dorset, DT2
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

The Cheesehouse is an exceptional, pet-friendly five-bedroom home resting in Litton Cheney, Dorset featuring a games room with pool, darts and bar area. Dorchester 9.9 miles; Yeovil 20.9 miles. (Ref. 1161994)

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


for 7 nights $2015

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