Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 672 cottages

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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 $708

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A patio with a round table and two chairs with two mugs on the table overlooking a gravel area and green hills at Burton Bay in Burton Bradstock
20
Burton Bradstock, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Pets welcome. Parking. 5 minute drive to Bridport, perfect couple romantic retreat. Wifi. Coastal views. (Ref. 994050)

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


for 7 nights $735

Last booked 2 days ago
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A stone cottage with a thatched roof next to a road with green planters under windows at Ivy Cottage in West Lulworth
26
West Lulworth, Dorset, BH20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Lovely thatched Grade II listed cottage for a family or friends. Welcomes two dogs. Original beams. Beach 1 mile. Pub 5 min. Seasonal shop 10 min. (Ref. 994302)

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


for 7 nights $1006

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An outdoor area with a round hot tub surrounded by potted plants and a seating area with chairs and an umbrella at Kingeswic Cottage in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This homely holiday cottage rests in Wyke Regis in Weymouth in Dorset. Pet-friendly. Nearby beach. Ideal for families. Isle of Portland 4.7 miles; Dorchester 9.4 miles; Bridport 18 miles. (Ref. 1050977)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Baby-friendly


for 7 nights $917

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An outdoor patio with a glass table set with wine glasses cheese and fruit overlooking the sea at Ocean Wave in Greenhill
19
Greenhill, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Beautiful apartment, that welcomes one well behaved dog, located on the esplanade, perfect for discovering the delights of Weymouth. With wifi and off-road parking for two small to mediums sized cars. (Ref. 994451)

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

  • $621 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights $1095

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A rocky jetty and small sandy beach by the sea with a garden and gated walkway in the foreground at Weymouth Bay Apartment B in Greenhill
32
Greenhill, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

First floor comfortable apartment sleeping up to 7 people close to the beach in Weymouth. Welcomes two dogs. Shared garden. Beach 2 min. Shop 10 min. Pub 5 min. Dorchester 7.6 miles. (Ref. 994772)

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


for 7 nights $793

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A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. Sea views. Elegant décor. Close to amenities. Dorchester 7.5 miles; Bridport 19.4 miles. (Ref. 1034440)

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


for 7 nights $774

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A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
27
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A well-positioned, fourth-floor apartment resting in Castletown, Dorset. Sea views. Close to amenities and the beach. Contemporary. Designated parking. Private balcony. Portland 1.9 miles; Weymouth 5.2 miles; Dorchester 12.6 miles. (Ref. 1119638)

  • Wi-fi
  • Swimming pool
  • Dishwasher
  • Washing machine


for 7 nights $735

Last booked 2 days ago
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A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. Beach 10 min. WiFi. Roadside parking. Shop and pub 5 min. Poole 32.5 miles. (Ref. 994432)

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


for 7 nights $1144

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A stone cottage with a green door and white framed windows with a garden and flowers at Norden Cottage in Osmington
33
Osmington, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Norden Cottage is a fine, three-bedroom abode resting in Osmington, Dorset. Woodburning stove. Pet-friendly. Enclosed garden. Close to amenities. Weymouth 4.9 miles. (Ref. 1149647)

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


for 7 nights $988

Last booked yesterday
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Stone terraced houses with white framed windows and a red door on a street at Bowman's Cottage Wakeham Portland
32
Wakeham, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A beautiful stone cottage, complete with garden on the quieter end of Portland, however situated on the main bus route to Weymouth and beyond. (Ref. 994021)

  • Wi-fi
  • Washing machine


for 7 nights $682

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A single-story brick building with a tiled roof and multiple doors and windows at Swallows Nest in Puxey near Sturminster Newton
38
Puxey near Sturminster Newton, Dorset, DT10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming stone-built barn conversion nestled on a working farm in the hamlet of Puxey, Dorset. Open-plan. En-suite. Views. Sturminster Newton 1.7 miles; Blandford Forum 10.3 miles. (Ref. 1066081)

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


for 7 nights $1212

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An outdoor patio with a table and chair under an umbrella a door and potted plants along a fence at Barrow Lodge in Winterborne Stickland near Blandford Forum
13
Winterborne Stickland near Blandford Forum, Dorset, DT11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A beautifully-presented, single-storey lodge residing in Winterborne Stickland near Blandford Forum, Dorset. Pet-friendly. Ground-floor living. In an AONB. Thornicombe 5.8 miles; Child Okeford 7.3 miles; Moors Valley Country Park & Forest 21.7 miles. (Ref. 1133242)

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


for 7 nights $529

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A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly


for 7 nights $743

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A stone house exterior with green door and lattice windows surrounded by garden at The Old School House in Piddletrenthide
32
Piddletrenthide, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

An attractive, converted Victorian school resting within Piddletrenthide. WiFi. Woodburning stove. Pet-friendly. Off-road parking. Dorchester 8 miles. (Ref. 933650)

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


for 7 nights $852

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A living room with leather sofas glass coffee table and large windows overlooking a marina at Harbourside Haven Penthouse 1 in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. WiFi. Views over the marina. Off-road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059266)

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


for 7 nights $820

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A cottage with a patio and garden at Droop Farm Cottage in Droop near Hazelbury Bryan
44
Droop near Hazelbury Bryan, Dorset, DT10
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A superb, Grade II listed cottage built of local stone and set deep in the Dorset countryside. WiFi. Pet-friendly. Yeovil 15.8 miles. (Ref. 988951)

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


for 7 nights $960

Last booked 2 days ago
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A brick house with blue door windows and a blue fence at Poppies Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Situated in a gated complex near Weymouth harbour. WiFi. Parking. Close to bars and restaurants. (Ref. 994560)

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

  • $344 off - Sat 20th Dec to 27th Dec 2025

  • $325 off - Sat 27th Dec 2025 to 3rd Jan 2026


for 7 nights $964

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A stone building with a tiled roof and wooden extension next to signs indicating walking routes and a cafe at The Cow Shed in Toller Porcorum
47
Toller Porcorum, Dorset, DT2
  • Sleeps15
  • Bedrooms9
  • PetsYes

    4.4★

    Good

  • Sykes rating

The Cow Shed, a welcoming cottage resting in the hamlet of Lower Kingcombe near Maiden Newton in Dorset, with a pet-friendly policy and on-site facilities. West Bay 11.1 miles; Lyme Regis 20.1 miles; Weymouth 20.4 miles. (Ref. 1150218)

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


for 7 nights $1508

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Front exterior of a cottage with a bench potted plant and a hanging basket at Spring Rose Cottage in Fortuneswell
38
Fortuneswell, Dorset, DT5
  • Sleeps8
  • Bedrooms3
  • PetsYes

    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)

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


for 7 nights $667

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