Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 670 cottages

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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 £631

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A patio with a table and chairs set outside a house with open glass doors and a large plant at Park Mews Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A stunning holiday home in the bustling seaside town centre of Weymouth in Dorset. Enclosed patio. Near beach. Smart TV. Isle of Portland 6.7 miles; Dorchester 8 miles; Bridport 20.2 miles. (Ref. 1054948)

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

  • 16% off - Thu 30th Oct 2025 to 3rd Jan 2026


for 7 nights £527

Last booked yesterday
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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 £434

Last booked yesterday
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A row of terraced houses with white and yellow facades and a sidewalk at Brewers Quay Harbour
29
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A delightful cottage situated next to Weymouth harbour in Dorset. Harbour Views. Family-friendly. Dorchester 8.4 miles; West Lulworth 15.5 miles. (Ref. 1061726)

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


for 7 nights £831

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A semi detached house with a driveway and a garage at Lagoon View in Wyke
33
Wyke, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming cottage based in the village of Wyke Regis, Dorset. Beach nearby. Dishwasher. Electric fire. Wifi. Weymouth 2.1 miles; Dorchester 9.7 miles. (Ref. 1121449)

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


for 7 nights £631

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A carport with gravel driveway and trees at The Halt in Maiden Newton
31
Maiden Newton, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles (Ref. 1165359)

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

  • 10% off - Sun 5th Oct to 30th Nov 2025

  • 10% off - Fri 5th Dec to 19th Dec 2025

  • 20% off - Sat 20th Dec 2025 to 2nd Jan 2026

  • 10% off - Sat 3rd Jan to 31st Jan 2026


for 7 nights £315

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An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
51
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of accommodation with en-suite facilities and vaulted ceiling. Dog-friendly, plenty to see and do in the area. Weymouth 3.5 miles. (Ref. 932158)

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


for 7 nights £622

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A kitchen area with a wooden countertop with fruit bowl wine bottle and glasses a small dining table with a bench seat by a window and a bar stool seating area at The Coach House - Trinity Lodge in Godmanstone near Cerne Abbas
25
Godmanstone near Cerne Abbas, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Trinity Lodge is a striking rural holiday home with great attention to detail, within the Dorset National Landscape, in Goodmanstone, near Cerne Abbas. Dorchester 5.3 miles; Weymouth 14 miles; Sherborne 14.3 miles; Yeovil 17.4 miles. (Ref. 1149594)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £399

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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 £402

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Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown
32
Puddletown, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7★

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £407

Last booked 2 days ago
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The front entrance of a building with a dark door numbered 38 and a curved window with plants along the path at Flat 2 38 Preston Road Weymouth
29
Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. Bike/kayak storage. En-suite. WiFi. Dorchester 6.3 miles; Isle of Portland 8.6 miles; West Lulworth 12.3 miles. (Ref. 1037083)

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


for 7 nights £491

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A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
18
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £472

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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★

    Perfect

  • 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


for 7 nights £2570

Last booked 2 days ago
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A house with outdoor seating area at Budmouth Upwey near Weymouth
42
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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


for 7 nights £622

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A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
36
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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


for 7 nights £731

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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

  • 10% off - Thu 30th Oct to 22nd Dec 2025


for 7 nights £1017

Last booked yesterday
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A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

An immaculate second-floor apartment resting in the centre of Weymouth. Marina views. Open-plan living room. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059264)

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


for 7 nights £631

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Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth
19
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A terrace property resting close to the beach and harbour in Weymouth. Allocated parking for two cars. WiFi. Fortuneswell 4.7 miles; Dorchester 8.9 miles. (Ref. 1038344)

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


for 7 nights £578

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A multi story residential building with large windows and a gravel driveway at Pointers View in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A well-presented, upper-ground floor apartment set in a contemporary development in Weymouth, Dorset. Beach nearby. Adults only. Smart TV. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1123114)

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


for 7 nights £620

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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

    4.7★

    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 £471

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