Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 682 cottages

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A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
28
Sutton Poyntz, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $589

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A white house with solar panels on the roof a lawn and a gravel garden at The White House in Weymouth
35
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This fabulous three-bedroom abode resides in Weymouth, Dorset. Sea glimpses. Smart TV. Open-plan. Near an AONB. Dorchester 7 miles; Bridport 19.5 miles. (Ref. 1125198)

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


for 7 nights $824

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A backyard with a glass conservatory attached to a stone and tile roof building and wooden outdoor furniture on a patio at Fossil Barn in Weymouth
18
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Contemporary barn conversion, close to the Dorset coast. Secluded garden. Solid oak flooring. Five minute drive to Weymouth. (Ref. 994207)

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

  • 5% off - Sat 1st Nov to 22nd Nov 2025


for 7 nights $841

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A kitchen with white cabinets marble countertops skylights and floral curtains at Upsidedown House Brewers Quay Harbour
25
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Located in a quiet location in Weymouth, Upsidedown House is a unique and beautiful holiday home. Pub and shop 2 min. Beach 10 min. Dorchester 8.4 miles. (Ref. 994746)

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


for 7 nights $1215

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 $987

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A wooden house with skylights and a small garden area surrounded by trees at Roman Lodge in Osmington
31
Osmington, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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


for 7 nights $926

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A street view of brick terraced houses with windows and front doors under a blue sky at Victoria House in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Victoria House is a pleasant holiday home resting in the coastal town of Weymouth in Dorset. Public car parking. Over three floors. Near amenities. Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1148491)

  • Wi-fi


for 7 nights $633

Last booked 3 days ago
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A brick townhouse with multiple windows and green hedges in front at Plain Sailing in Weymouth
42
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Plain Sailing, a gorgeous holiday home located in the heart of the marvellous seaside town of Weymouth, Dorset. En-suite master. Lake view. Pet-friendly. Dorchester 7.8 miles; Bridport 18.6 miles. (Ref. 1153879)

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


for 7 nights $952

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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★

    Outstanding

  • 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


for 7 nights $806

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A brick residential building with white doors and windows next to a small lawn and paved driveway at Lodmoor House in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Wi-fi
  • Washing machine


for 7 nights $737

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Quay Cottage - 994576 - photo 1
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Quay cottage is a period terraced property in Weymouth. Short walk to town centre. Close to Old Harbour. WiFi. Pub and shop 5 min. Beach 10 min. Dorchester 8.5 miles. (Ref. 994576)

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


for 7 nights $784

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A street view of a row of attached brick houses with dormer windows and a sidewalk at Marina Reach in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Ground floor apartment in Weymouth, sleeps 4, wifi, allocated parking, close to the beach, shops and marina. Open plan living kitchen diner. (Ref. 1091449)

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


for 7 nights $700

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A three-story red brick residential building with multiple white-framed windows and black doors at Admiral's Quarter Apartment 5 in Weymouth
11
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A well-presented, ground-floor apartment in Weymouth, Dorset. Open-plan. Close to beach. Near an AONB. Ground-floor living. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1126298)

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


for 7 nights $570

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A house with stone and wooden exterior at Everdene Upwey near Weymouth
46
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

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


for 7 nights $920

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A white two-story house with bay windows and a dark front door at Bay Cottage in Weymouth
50
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. Smart TV. Decking with furniture. Near a beach. Dorchester 8.4 miles; Bridport 20.3 miles. (Ref. 1139723)

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


for 7 nights $1357

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A brick and white building facade with multiple windows on Trinity Road
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A Grade II listed, spacious maisonette apartment over the first and second floor in the Dorset town of Weymouth. WiFi. One dog welcome. Pub and shop within 0.1 miles. (Ref. 1011525)

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


for 7 nights $1080

Last booked yesterday
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A front view of a large brick and white house with bay windows and a small porch at Dream View in Greenhill
24
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Located on the Esplanade in Weymouth with far reaching beach and sea views and within walking distance of the Harbour and town amenities. (Ref. 994167)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $824

Last booked yesterday
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Two adjacent houses with black front doors and small porches with awnings and shrubs outside at Anvil House in Brewers Quay Harbour
25
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A pretty little modern house just a few minutes walk from the harbourside and local amenities. Close to the South West Coast Path. (Ref. 993929)

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


for 7 nights $747

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A living room with a wooden coffee table two patchwork chairs a fireplace and a window with an ocean view at Beach Retreat in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A sea-front two-bedroom apartment fronting Weymouth bay, Dorset. Beautiful views. En-suite bedroom. Woodburning stove. Near beach. Dorchester 7.6 miles; Bridport 21.3 miles; Poole 31.4 miles. (Ref. 1100406)

  • Wi-fi
  • Dishwasher


for 7 nights $833

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An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
33
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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


for 7 nights $912

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