Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 674 cottages

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The exterior wall of a yellow building with a white door and window and potted plants along the wall at Cuckoo Cottage in Bridport
19
Bridport, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A romantic pied-a-terre in the bustling market town of Bridport. Close to the Jurassic Coast. Parking. WiFi. Open-plan living. (Ref. 1004940)

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


for 7 nights £415

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A brick and flint house with a slate roof and an outdoor patio area with wooden table and chairs surrounded by flowering plants at Churn House in Dewlish
15
Dewlish, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

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Beautiful barn conversion positioned in the lovely village of Dewlish in Dorset. Off-road parking. Shared outdoor heated pool. Pet-friendly. Shop 1.8 miles, pub 0.2 miles. (Ref. 1003641)

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


for 7 nights £796

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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 £537

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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

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    A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth
    16
    Weymouth, Dorset, DT4
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.5★

      Outstanding

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    A modern studio apartment on the seafront on Weymouth, Dorset. Open-plan living. Sea views. Perfect for couples. (Ref. 1003545)

    • Wi-fi
    • Dishwasher
    • Washing machine


    for 7 nights £423

    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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    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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    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 £524

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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 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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    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 £634

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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

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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 garden with grass and flowerbeds in front of a blue bungalow with a veranda and outdoor chairs at Harbour View Bungalow in Weymouth
    30
    Weymouth, Dorset, DT4
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Sykes rating

    Overlooking the beautiful Nothe Gardens and, through the trees, the coastal views of Weymouth Bay and Portland Harbour is Harbour View Bungalow. (Ref. 994244)

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


    for 7 nights £1206

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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 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

    Last booked yesterday
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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 £594

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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 £819

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    A building with balconies and stairs in front with a palm tree on the side at Lookout in Cove Castle
    38
    Cove Castle, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Sykes rating

    Comfortable Spanish style holiday home in Weymouth. Off road parking for two cars. Patio garden with furniture. Sea views. Beach 5 min. Pub and shop 10 min. Dorchester 9 miles. (Ref. 994352)

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


    for 7 nights £671

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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 £636

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