Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 670 cottages

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A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
14
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • $189 off - Mon 29th Dec 2025 to 6th Jan 2026


for 7 nights $996

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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 $925

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Front exterior of a brick house with white-framed windows and door and garden shrubs with black chairs and table outside at Splash in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Splash, a lovely, terrace cottage lies in the heart of Weymouth, a seaside town in Dorset. Near beach and pub. Smart TV. Near harbour. Dishwasher. Dorchester 8.6 miles; Bridport 19.4 miles. (Ref. 1154894)

  • Wi-fi
  • Off-road parking
  • Dishwasher

  • $442 off - Mon 22nd Dec to 29th Dec 2025

  • $442 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights $836

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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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


for 7 nights $871

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

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


for 7 nights $835

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A single-story building with mixed stone and brick walls a green door and multiple windows beside a gravel pathway and picnic table at Hebe in Notton near Maiden Newton
34
Notton near Maiden Newton, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A delightful, two-bedroom barn conversion resting in Notton, Dorset. Disabled-friendly. Dog-friendly. Eco-friendly. Enclosed garden. West Bay 15 miles; Weymouth 16.2 miles; Lyme Regis 24 miles. (Ref. 1096950)

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


for 7 nights $976

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A corner seating area with two black armchairs near bay windows and a side table with a lamp at Two @ No36 in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Two @ No36, a wonderful, first-floor apartment situated in the heart of Weymouth in Dorset, with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162203)

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


for 7 nights $962

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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 $1144

Last booked yesterday
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A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

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


for 7 nights $835

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A coastal view with boats on water and a hill in the background at Portland Pebble in Wyke Regis
43
Wyke Regis, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

An enticing, semi-detached house sitting in Wyke Regis, Dorset. Sea views. Near the beach and coast. Balcony. Weymouth 3.3 miles; Isle of Portland 3.8 miles; Dorchester 10.3 miles. (Ref. 1097679)

  • Wi-fi
  • Off-road parking


for 7 nights $930

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A brick house with white framed windows and door with two black chairs and a small table outside at Nuke in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

This cottage boast style, character, and a fabulously contemporary interior. Central location. Surrounded by history. WiFi. Rodwell 0.9 miles. (Ref. 1005313)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • $309 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights $836

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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
68
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 $1370

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A single-story house with a tiled roof and a paved driveway near the ocean at Beach Haven in West Bexington
33
West Bexington, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Detached chalet bungalow in West Bexington, Dorset. Large garden with sea views. Close to beach. WiFi. Abbotsbury 4.8 miles; Bridport 6.8 miles. (Ref. 1017936)

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


for 7 nights $1599

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Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

  • 16% off - Thu 30th Oct 2025 to 5th Jan 2026


for 7 nights $1294

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A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
59
Osmington, Dorset, DT3
  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

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


for 7 nights $4479

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A two-story brick house with a white entrance porch and cobblestone driveway at The Chocolate Box in Weymouth
37
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely three-storey house resting in Weymouth, Dorset. Dog-friendly. Near a beach. Off-road parking. Private garden. Dorchester 8.7 miles; Bridport 19.1 miles. (Ref. 1092302)

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


for 7 nights $1048

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A dining table with flowers butter croissants orange juice and jam by windows overlooking a beach at Grandview in Weymouth
47
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Easter Weekend open to book! A characterful first-floor apartment set on the Dorset coast, within the town of Weymouth. Outstanding sea views. Central location. Family-friendly. Isle of Portland 7 miles; Dorchester 7.2 miles; West Bay 18.1 miles. (Ref. 1049890)

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


for 7 nights $1204

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A living room with two grey sofas and a wooden boat-shaped shelf with books at Chesil Retreat Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

  • 15% off - Fri 19th Dec to 26th Dec 2025

  • 15% off - Fri 26th Dec 2025 to 2nd Jan 2026


for 7 nights $820

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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 $723

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A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport
45
Uploders near Bridport, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. Enclosed garden. Romantic. In an AONB. Close to amenities. West Bay 5 miles; Lyme Regis 14.1 miles. (Ref. 1117867)

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


for 7 nights $545

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