Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 670 cottages

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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 £812

Last booked yesterday
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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

  • £294 off - Mon 29th Dec 2025 to 6th Jan 2026


for 7 nights £913

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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 £1010

Last booked yesterday
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A stone thatched roof cottage with white framed windows and a porch along a quiet street at Cobblers Cottage in Langton Herring
44
Langton Herring, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Cobblers Cottage is a traditional stone built thatched cottage in the quiet Dorset village of Langton Herring, close to the Jurassic coast. Abbotsbury 5 miles; Weymouth 5.5 miles; Portland 9.4 miles; Dorchester 9.9 miles. (Ref. 1171904)

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


for 7 nights £497

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The front door of Clematis House next to a pathway with flowers and a street lamp in Charlton Down near Dorchester
24
Charlton Down near Dorchester, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A charming semi-detached house resting in Charlton Down, Dorset. Enclosed garden. Private parking. WiFi. Open-plan. Family-friendly. Godmanstone 2.7 miles; Dorchester 3.9 miles; Weymouth 12.9 miles. (Ref. 1076739)

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


for 7 nights £537

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A garden with a shed and patio overlooking a bay with sailboats at Rainbow's End in Cove Castle
27
Cove Castle, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)

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


for 7 nights £689

Last booked yesterday
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A corner of a living room with a bay window showing a view outside and a TV on a white cabinet at Waterside in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)

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


for 7 nights £667

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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 £610

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A living room with a TV on a stand a coffee table with board games a clock on the wall and large windows showing a sea view at Beach View Apartment 3 in Greenhill
19
Greenhill, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Directly on the seafront. First floor period apartment. Bright and comfortable. Breath-taking sea views. En-suite shower room. WiFi. Off road parking with garage. (Ref. 993989)

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


for 7 nights £676

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The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour
26
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights £516

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A row of brick terraced houses with white doors and windows along a street at Castle Cove View in Castle Cove
29
Castle Cove, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. Sea views. Sleeps 6. Off road parking (Ref. 1059103)

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


for 7 nights £856

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Front of a red brick terraced house with white door and windows and plants in front at Rockpools in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Sleeping four in Maltings area of Weymouth, pet friendly. Off road parking. WiFi. Garden. Close to harbour. (Ref. 994596)

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


for 7 nights £567

Last booked yesterday
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A living room with a sofa, table, and kitchen area at Royal Terrace Sunset in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Royal Terrace Sunset is a contemporary apartment situated along the coast in the heart of Weymouth, Dorset, boasting a short walk to a pub and shop. Dorchester 7.7 miles; Bridport 18.9 miles. (Ref. 1173496)


    for 7 nights £475

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    Front view of a brick house with white framed windows a white door two black chairs and a palm tree at Reaver Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Sykes rating

    Sleeping four near harbourside in Weymouth. Welcome two dogs. Pubs, restaurants and harbour 5 mins walk. (Ref. 994584)

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

    • £351 off - Mon 22nd Dec to 29th Dec 2025

    • £289 off - Mon 29th Dec 2025 to 5th Jan 2026


    for 7 nights £697

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    Exterior of a row of white buildings with balconies and doors including a restaurant named ENZO at Bliss On The Bay Weymouth
    24
    Weymouth, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Sykes rating

    A stylish apartment resting on Weymouth's beautiful esplanade. Sleeps 4. Opposite beach. Off road parking. WiFi. Dorchester 7.3 miles; Bridport 20.3 miles. (Ref. 1067722)

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


    for 7 nights £614

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    Exterior view of a stone house with multiple wooden windows and a wooden door next to outdoor dining furniture at The Granary Burton Bradstock
    33
    Burton Bradstock, Dorset, DT6
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Sykes rating

    A beautifully presented property resting in the pretty village of Burton Bradstock. Off-road parking. WiFi. Woodburning stove. Bridport 2.9 miles; Weymouth 15.8 miles; Dorchester 16.4 miles. (Ref. 1069147)

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


    for 7 nights £1043

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    A dining table set with plates glasses and bread next to a living room with sofa armchairs coffee table and glass doors with green curtains at Newton's Cove View in Weymouth
    21
    Weymouth, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Sykes rating

    Upper ground floor apartment in the Admiral’s Quarter development. Partial sea views from the full length windows in the sitting rooms. Modern furnishings. Perfect for a family holiday exploring the delights of Weymouth. Wifi. (Ref. 994438)

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


    for 7 nights £574

    Last booked 2 days ago
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    The front exterior of a brick house with a black door and white framed windows surrounded by green bushes at Admirals Quarter Apartment 4 in Weymouth
    30
    Weymouth, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Sykes rating

    Modern ground floor Apartment. Lovely walks through the Nothe Gardens. Short walk to town centre and the beach. Wi-Fi. Gated Parking. (Ref. 993910)

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

    • £155 off - Mon 29th Dec 2025 to 5th Jan 2026


    for 7 nights £466

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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 £695

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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
    16
    Weymouth, Dorset, DT4
    • Sleeps2
    • Bedrooms1
    • PetsNo

      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 £498

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