Dorchester Cottage Holidays

Your Dorchester, Dorset search returned 701 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A charming, three-bedroom cottage sitting in Chickerell, Dorset. Close to amenities. Enclosed garden. Off-road parking. Weymouth 3.3 miles; Abbotsbury 5.9 miles; Portland 7.2 miles. (Ref. 1086432)

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


for 7 nights From £703

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

The Old Dairy is Travellers Rests’ largest stone-built cottage, a converted farm building made for relaxed stays with families, groups and dogs. West Bay 4.7 miles; Lyme Regis 13.8 miles; Weymouth 17.7 miles. (Ref. 1099459)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £467

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

Modern and comfortable holiday house for up to 8 people in the Isle of Portland. Enclosed garden with patio. Pub and shop 5 min. Beach 5 min. Weymouth 5 miles. (Ref. 994310)

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


for 7 nights From £998

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. Attractive, well-appointed and modern holiday cottage. Many attractions and activities within reach. Weymouth 3.5 miles. (Ref. 932159)

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


for 7 nights From £593

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A charming holiday home resting near Shipton Bradstock, Dorset. Dog-friendly. Woodburing stove. Close to beach. Bridport 2.7 miles; Dorchester 13.7 miles; Weymouth 19.8 miles; Yeovil 20.7 miles. (Ref. 1074488)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 17th Apr to 30th Jun 2026


for 7 nights From £717

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.3

    Good

  • Sykes rating

Sunset View is a perfectly-positioned, fifth-floor apartment residing in Castletown, Dorset. Sea views. Close to amenities and the beach. Private balcony. Portland 2.1 miles; Weymouth 5 miles; Dorchester 12.4 miles. (Ref. 1141111)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights From £508

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A fabulous, three-storey home resting near Weymouth's Old Harbour in Dorset. Close to amenities, beach and attractions. Near AONB. Open-plan living. Stylish. Dorchester 8.8 miles; West Lulworth 15.8 miles. (Ref. 1092575)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £696

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

A beautiful quirky cottage in Beaminster in Dorset. Romantic. Woodburning stove. Open-plan. Beaminster 0.5 miles; Charmouth 13.7 miles; Lyme Regis 15.6 miles; Seaton 20.5 miles. (Ref. 1106445)

  • Pet friendly (extra charges may apply)
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 7 nights From £523

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Detached property in village of Sutton Poyntz. 3 bedrooms. 2 dogs. Off road parking for two cars. (Ref. 994127)

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


for 7 nights From £823

Last booked 3 days ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Superb single-storey barn conversion near Winterborne Stickland in an Area Of Outstanding Natural Beauty. Open plan living with beams and en suite-facilities. Woodburning stove. Blandford Forum 4 miles. (Ref. 19285)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights From £457

  • Sleeps8
  • Bedrooms3
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A charming terraced property resting in Fortuneswell, Dorset. Sea views. WiFi. Terrace garden. Pet-friendly. Weymouth 5.2 miles. (Ref. 1035417)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £429

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Dirdale is a tasteful lodge resting in rural Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105458)

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


for 7 nights From £677

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

  • Pets go free
  • Wi-fi
  • Baby-friendly


for 7 nights From £474

Last booked 2 hours ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Coastguard View is a lovely holiday cottage resting near the coast in Portland Bill on the Isle of Portland, Dorset with a Smart TV and open-plan space. Easton 2.6 miles; Fortuneswell 3.6 miles; Weymouth 9.1 miles. (Ref. 1169819)

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


for 7 nights From £600

Last booked 1 hour ago
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Perfect cottage to base yourself surrounded by the beautiful Dorset countryside. Ideal for elderly and families as all on one level. Off road parking and wifi (Ref. 994231)

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


for 7 nights From £564

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

A charming single-storey holiday home nestled in the quaint village of Eype, Dorset. Ground-level living. Garden. Sea views. Bridport 2.2 miles; West Bay 3 miles. (Ref. 1078226)

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


for 7 nights From £537

Last booked yesterday
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  • Sleeps6
  • Bedrooms4
  • Pet FriendlyYes

    4.3

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

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


for 7 nights From £851

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Modern and spacious cottage for couples or family in the Isle of Portland. Enclosed garden. Welcomes one dog. Pub and shop 10 min. Beach 5 min. Weymouth 5 miles. (Ref. 994497)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £638

  • Sleeps4
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

Backlands Farmhouse is a charming holiday cottage nestled in the seaside village of Charmouth, along the Jurassic Coast. Close to beach and amenities. Lyme Regis 3 miles; Axminster 5.6 miles; Bridport 6.8 miles. (Ref. 1149648)

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


for 7 nights From £608