Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 676 cottages

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A street view of a blue painted building with white framed windows and two white doors in a row of attached houses
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Sykes Rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. Off-road parking. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £809

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A stone building facade with multiple windows flower boxes and a wrought iron fence at The Esplanade in Weymouth
85
Weymouth, Dorset, DT4
  • Sleeps18
  • Bedrooms9
  • PetsNo

    5.0

    Sykes Rating

The Esplanade is a stunning, nine-bedroom holiday dwelling residing in Weymouth, Dorset. Sea views. En-suite bedrooms. Close to amenities and a beach. Parking. Dorchester 7.2 miles; Bridport 18.7 miles. (Ref. 1123341)

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

7 nights from £2570

Last booked yesterday
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A two-story brick house with a white enclosed porch shrubs in front and a driveway leading to a detached garage at Casa Carmen in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.1

    Sykes Rating

Modern, detached cottage resting on the edges of Weymouth in Dorset. Off-road parking. Garden. WiFi. Close to harbour, shops, restaurants and pubs. (Ref. 1001584)

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

7 nights from £641

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A stone cottage with a thatched roof and a wooden table and benches outside at Magnolia Cottage Osmington
41
Osmington, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3

    Sykes Rating

Magnolia cottage is situated in Osmington. Pretty, thatched and very well-equipped. High chair and cot. Wifi. Parking for two cars. Pub 5 min. Weymouth 4.5 miles. (Ref. 994367)

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

7 nights from £566

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A single-story house with a garage and a lawn at Shipton Hill View in Shipton Gorge
36
Shipton Gorge, Dorset, DT6
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Sykes Rating

Situated in a stunning loaction overlooking hills in Dorset. Ground floor accommodation with doors from lounge opening onto large garden. Welcomes two pets. (Ref. 994654)

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

7 nights from £865

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A brick house with a white door and windows surrounded by a lawn and gravel pathway at Old Rectory Cottage in Sturminster Newton
20
Sturminster Newton, Dorset, DT10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Sykes Rating

A detached, character cottage nestled in the rural village of Manston near Child Okeford in Dorset. Countryside views. Woodburning stove. Country-style. Shaftesbury 6 miles; Blandford Forum 8.9 miles. (Ref. 1072821)

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

7 nights from £507

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A brick residential building with white front doors and windows surrounded by shrubs at 2 Bathsheba Terrace in Dorchester
28
Dorchester, Dorset, DT1
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Sykes Rating

A charming two-bedroom holiday home settled in Dorchester, Dorset. Washing machine. Enclosed garden. Gas fire. Close to amenities. Weymouth 8.9 miles; West Bay 17.3 miles. (Ref. 1096658)

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

7 nights from £460

Last booked 2 days ago
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The exterior of a pink two-story house with a blue door and large window at Lyme View in Fortuneswell
38
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

Lyme View, delightful coastal property resting in Fortuneswell on the Isle of Portland, Dorset. Close to a beach. Garden. Pet friendly. Close to a shop and a pub. Weymouth 5.2 miles; Abbotsbury 11.9 miles; Dorchester 12.8 miles. (Ref. 1135049)

  • Wi-fi
  • Electric vehicle charging
  • Washing machine

7 nights from £937

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A stone house with tiled roof and wooden bench surrounded by gravel driveway and trees at Pound Cottage in Kingcombe near Maiden Newton
27
Kingcombe near Maiden Newton, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.5

    Sykes Rating

This is a detached cottage in Lower Kingcombe, near the village of Maiden Newton in Dorset. Original features. Exposed beams and brickwork. Private orchard garden. West Bay 11.1 miles; Weymouth 19.2 miles; Lyme Regis 20.2 miles. (Ref. 1015347)

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

7 nights from £371

Last booked yesterday
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A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • PetsNo

    4.4

    Sykes Rating

Three bedroom terraced property in central Weymouth. Open plan living area. (Ref. 1095056)

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

7 nights from £722

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A balcony with a railing and glass doors overlooking a harbor and buildings at The Penthouse in West Bay
Offer
21
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

An impressively stylish apartment close to picturesque West Bay in Dorset. Stylish. Sea views. Great location. WiFi. West Bay 0.1 miles; Bridport 1.9 miles; Lyme Regis 11.3 miles. (Ref. 1106214)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 30% off - Fri 22nd Aug to 31st Aug 2025

  • 20% off - Fri 19th Sep to 30th Sep 2025

7 nights from £1343

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Exterior of a stone cottage with a thatched roof white door and windows with plants around the entrance at Lilac Cottage in Burton Bradstock
29
Burton Bradstock, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Sykes Rating

Character cottage in the coastal village of Burton Bradstock, sleeping four. Two dogs. Local shop and pubs. Coastal walks. (Ref. 994332)

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

7 nights from £630

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A row of modern brick and beige townhouses with balconies and large windows behind a green hedge at Kiama in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Sykes Rating

A well-positioned, three-storey property resting in Weymouth, Dorset. Sea views. Close to amenities and the beach. Enclosed garden. Elevated position. Dorchester 8.9 miles; Bridport 20.6 miles. (Ref. 1118939)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £602

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Two boats moored in a harbor with modern apartment buildings and parked cars in the background at Harbour View in West Bay
16
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Sykes Rating

A ground-floor apartment resting in West Bay, Dorset. Sea view. Close to a beach. Close to the town centre. Charmouth 8.5 miles; Lyme Regis 11.3 miles; Weymouth 18.2 miles. (Ref. 1106378)

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

7 nights from £685

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Two small wooden huts with open doors on grass surrounded by trees and two wooden chairs with a tree stump table at Sika in Warmwell
New property
19
Warmwell, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

    Sykes Rating

Sika is a tremendous hut near the village of Broadmayne, Dorset, boasting exceptional countryside views all around as well as a woodburning stove. Dorchester 5.8 miles; Weymouth 8.2 miles; Bridport 20.6 miles; Swanage 21 miles. (Ref. 1174453)

  • Off-road parking
  • Ground floor bedroom

7 nights from £708

Last booked 1 hour ago
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An outdoor area with green grass a small green cabin with a porch and two wooden chairs at Hurdlemakers Hut in Piddletrenthide
33
Piddletrenthide, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

This charming, one-bedroom holiday lodge rests in Piddletrenthide, Dorset. Open plan. Ground-floor living. Romantic. Countryside views. Dorchester 8.9 miles. (Ref. 1131510)

  • Wi-fi
  • Ground floor bedroom

7 nights from £598

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A living room with sofas a patterned rug a TV and a fireplace at Brewers House in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.4

A tasteful, three-storey Victorian terrace cottage in the popular Dorset resort of Weymouth. Central location. WiFi. Near Dorset AONB. (Ref. 1002126)

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

7 nights from £825

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A living room with an orange armchair green sofa and ottoman wooden bookcase and hanging plants at Harbour Retreat in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

Harbour Retreat is a delightful three-storey cottage by the harbourside in Brewers Quay Weymouth, Dorset. Close to beach, shops and amenities. Dishwasher. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1139963)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £614

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A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Sykes Rating

Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. Ground-floor living. Near to shop and pub. En-suite. Dorchester 8.5 miles; Bridport 17.5 miles. (Ref. 1152691)

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

7 nights from £639

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A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Sykes Rating

A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. Excellent location. Smart TV. WiFi. Dorchester 7.4 miles; Bridport 18.8 miles. (Ref. 1123724)

  • Wi-fi

7 nights from £557

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