Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 677 cottages

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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


for 7 nights $848

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A stone house with diamond lattice windows and a green door surrounded by trees at Warmwell Lodge in Warmwell
28
Warmwell, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Lovely early Victorian style Grade II listed cottage set in Warmwell village. Sleeps four guests. Garden. Welcomes two small dogs. Pub 3 miles. Shop 2 miles. Dorchester 6 miles. (Ref. 994760)

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


for 7 nights $725

Last booked yesterday
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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 $828

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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 $639

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A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
41
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. Close to amenities and harbour. Pet-free. Garden. Dorchester 8.7 miles; West Lulworth 15.8 miles. (Ref. 1093760)

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


for 7 nights $815

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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 $840

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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


for 7 nights $733

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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 $830

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A small outdoor seating area with chairs and a table surrounded by flowers in front of a brick house with blue shutters at Garibaldi Cottage in Weymouth
38
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Garibaldi Cottage is a lovely, coastal home resting in the town of Weymouth in Dorset, enjoying close proximity to a nearby shop, beach, and pub. Dorchester 8.2 miles; Bridport 20.1 miles. (Ref. 1156408)

  • Wi-fi
  • Washing machine
  • Baby-friendly

  • 15% off - Wed 1st Oct to 1st Nov 2025


for 7 nights $634

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

    4.7★

    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 $647

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A detached house with a double garage and driveway at Connaught Gardens in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Large, modern house nestled on the outskirts of Weymouth, 1 mile from the beach and restaurants. Off-road parking. WiFi. Enclosed garden. (Ref. 1001446)

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


for 7 nights $1025

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A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock
17
Burton Bradstock, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A brightly decorated property resting within the village of Burton Bradstock. Pet-friendly. WiFi. Pub and shop within 0.2 miles. Weymouth 15.7 miles. (Ref. 1008498)

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


for 7 nights $626

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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 $626

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    A stone barn with wooden doors and windows with a paved patio and picnic bench with grass and gates at Warehams Barn in Puncknowle near Burton Bradstock
    36
    Puncknowle near Burton Bradstock, Dorset, DT2
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Sykes rating

    A superb barn conversion resting in Puncknowle near Burton Bradstock, Dorset. WiFi. Balcony. Rural location. Bridport 6.5 miles; Weymouth 12.9 miles; Swanage 38.7 miles. (Ref. 1098014)

    • Wi-fi
    • Washing machine
    • Baby-friendly


    for 7 nights $759

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    An exterior view of Wren Cottage in Weymouth
    16
    Weymouth, Dorset, DT4
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • 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 $487

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    A fenced swimming pool with chairs and lawn in front of a brick and wood house at Manor Farm Barn in Dewlish
    42
    Dewlish, Dorset, DT2
    • Sleeps15
    • Bedrooms8
    • PetsYes

      4.8★

      Outstanding

    • Tourist Board rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Wonderfully appointed barn conversion residing in the sleepy village of Dewlish in Dorset. Dog-friendly. Off-road parking. Shared outdoor heated pool. Dorchester 7 miles. (Ref. 1003646)

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

    • $68 off - Sat 18th Oct to 25th Oct 2025


    for 7 nights $3144

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    Front view of a brick terraced house with bay windows and a black front door at Pedaller's Cottage in Weymouth
    16
    Weymouth, Dorset, DT4
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Sykes rating

    Located in a quiet residential street in Weymouth, Pedaller’s cottage is a delightful home for families. Short walk to town. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8.6 miles. (Ref. 994539)

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


    for 7 nights $1059

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    An outdoor balcony with a table set with plates cups a teapot and pastries with buildings in the background at Spindrift Brewers Quay Harbour
    38
    Brewers Quay Harbour, Dorset, DT4
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Sykes rating

    Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)

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


    for 7 nights $855

    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


    for 7 nights $1167

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    A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock
    27
    Burton Bradstock, Dorset, DT6
    • Sleeps2
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Sykes rating

    A brightly decorated property resting within the village of Burton Bradstock, Dorset. Couples retreat. Pet-friendly. Close to amenities and beach. Bridport 3.1 miles; Weymouth 15.7 miles; Dorchester 15.5 miles; Yeovil 22.4 miles. (Ref. 1118787)

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


    for 7 nights $572

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