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Dorset Holiday Cottages

Your Dorset search returned 1,060 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
Exterior of a single story stone and brick cottage with black windows and doors and two flower pots at Keepers Cottage in Winterborne Stickland
1 of 42
5
Winterborne Stickland, Dorset, DT11
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Charming, characterful, single-storey barn conversion. Attractive lawned courtyard in Area of Outstanding Natural Beauty. Family accommodation with en-suite, woodburner, shared games room on site. Blandford Forum 4 miles. (Ref. 905895)

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


for 7 nights From $621

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A small building with a red tiled roof white walls white double doors and climbing plants next to a gravel path and grass at Oke Apple Cottage in Okeford Fitzpaine
1 of 11
5
Okeford Fitzpaine, Dorset, DT11
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Charming, detached single storey barn conversion. Lovely Dorset cottage in rural location. Open plan accommodation. Use of swimming pond. Sturminster Newton 4 miles. (Ref. 20119)

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


for 7 nights From $470

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A garden with a wooden bench surrounded by plants and a brick house in the background at ODYSEA in Weymouth
Offer
1 of 48
5
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

With off road parking for 2 cars and just a short 3-minute walk to the old harbour, town centre and beach beyond, this fully modernised 1900 cottage with 3 bedrooms, more importantly 3 bathrooms with 2 receptions and a sunny south facing garden is a steal (Ref. 1099795)

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

  • $492 off - Sat 29th Aug to 5th Sep 2026


for 7 nights From $1092

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An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
1 of 35
5
Greenhill, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

Excellent period apartment in Weymouth close to the esplanade. Two en-suite shower rooms and three bedrooms. WiFi. Enclosed patio area. Beach 1 min away. (Ref. 993988)

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


for 7 nights From $1421

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A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
1 of 27
5
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

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


for 7 nights From $735

Last booked 7 hours ago
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An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth
1 of 16
5
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

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


for 7 nights From $682

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A harbor with boats docked and modern buildings in the background at The Boardwalk in West Bay
1 of 19
5
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Central location of West Bay, 1st floor apartment. Two bedrooms. Harbour views. Central location. Balcony over harbour. Beach few moments walk from property. Nearby bars and restaurants. (Ref. 994014)

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


for 7 nights From $1195

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A stone house with white framed windows garden with trimmed bushes and an outdoor seating area at Pomme Blushe House in Shipton Gorge
1 of 40
5
Shipton Gorge, Dorset, DT6
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

Pomme Blushe House, a stunningly-presented stone cottage located outside of the charming town of Bridport, Dorset. Pet-friendly. Garden with hot tub. Lyme Regis 13 miles; West Bay 3.8 miles. (Ref. 1150821)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From $1301

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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
1 of 40
5
Litton Cheney, Dorset, DT2
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.6★

    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)

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


for 7 nights From $1986

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A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
1 of 38
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. Dorchester 8.5 miles; Bridport 20.5 miles; Poole 32.2 miles. (Ref. 1107935)

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


for 7 nights From $755

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A living room with sofas a round coffee table dining table and chairs with a view of the sea at 1 Ocean Bay Swanage
1 of 40
5
Swanage, Dorset, BH19
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A stunning two-bedroom, first-floor apartment resting in Swanage, Dorset. Near a beach. Sea views. Barbecue. Smart TV. Wareham 9.7 miles; Poole 19.6 miles. (Ref. 982988)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $1455

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A kitchen with yellow stools and blinds with wooden floor and countertop at Seashore in Lyme Regis
1 of 17
5
Lyme Regis, Dorset, DT7
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

A quaint apartment over three floors within a short walk of Lyme Regis in Dorset. Great location. Stylish. Romantic. WiFI. Lyme Regis 0.1 miles; Axminster 5.6 miles; Seaton 7.9 miles; Bridport 9.8 miles; Abbotsbury 19 miles. (Ref. 1106571)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $622

Last booked 2 days ago
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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
1 of 37
5
Winterborne Stickland, Dorset, DT11
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    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)

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


for 7 nights From $734

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A balcony with a table and chairs overlooking a garden and sea at The View in Weymouth
1 of 46
5
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

The View is a charming, three-storey house resting near the beach in Weymouth, Dorset, boasting stunning sea views, a balcony, and off-road parking. Dorchester 8.9 miles; Bridport 19.2 miles. (Ref. 1173086)

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


for 7 nights From $811

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The exterior of a white house with windows a brick wall and a garden with trees and a small pond at Riverside 67 Dorchester Road in Maiden Newton
1 of 40
5
Maiden Newton, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7★

    Outstanding

  • Sykes rating

A stunning terraced nestled in the large village of Maiden Newton in Dorset. Woodburning stove. Riverside views. Eco-friendly. West Bay 12.4 miles; Weymouth 17 miles; Lyme Regis 22.4 miles. (Ref. 1070251)

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


for 7 nights From $1003

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A stone house with green garage doors and white windows next to a building with a boarded-up window at Swanage Driftwood in Swanage
1 of 37
5
Swanage, Dorset, BH19
  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Sleeps 10, large open plan living kitchen dining room. 3 bathrooms, central Swanage location close to the beach. WiFi. (Ref. 994706)

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


for 7 nights From $1615

Last booked 2 days ago
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A detached house with blue upper walls and red brick lower walls with large bay windows and a paved driveway at 20 Ulwell Road in Swanage
1 of 46
5
Swanage, Dorset, BH19
  • Sleeps14
  • Bedrooms7
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

This large detached Edwardian House. Seven bedrooms. Perfect for families and large groups. Woodburners. Three floors. Wareham 9.7 miles; Poole 20 miles. (Ref. 980319)

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


for 7 nights From $1806

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A row of houses with white and blue walls and small gardens along a brick pathway at Little Tern Brewers Quay Harbour
1 of 31
5
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

A delightful, mid-terrace cottage resting in Brewers Quay Harbour, Dorset. Designated parking. Pet-friendly. Enclosed garden. Weymouth 0.6 miles; Dorchester 8.8 miles; West Lulworth 15.7 miles. (Ref. 1084006)

  • Pets go free
  • Dishwasher
  • Washing machine


for 7 nights From $815

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A corner seating area with striped and patterned cushions a floor lamp and a window seat overlooking the beach and sea at Starfish in Lyme Regis
1 of 18
5
Lyme Regis, Dorset, DT7
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

An impressive second-floor apartment in the heart of Lyme Regis. Spacious. Sea views. Open-plan. WiFi. Lyme Regis 0.1 miles; Bridport 9.7 miles; Sidmouth 16.3 miles. (Ref. 1106018)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $1012

Last booked 2 days ago
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Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown
1 of 32
5
Puddletown, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.8★

    Outstanding

  • Sykes rating

Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. Dorchester 5.5 miles. (Ref. 1160443)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $563

Last booked yesterday
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