Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 676 cottages

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A stone and brick cottage with a tiled roof and a small garden beside a road at Way's Forge in Piddlehinton
24
Piddlehinton, Dorset, DT2
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. Sleeps 3 people. Garden. Welcomes 2 dogs. Shop 2-3 miles. Pub 2 min. Dorchester 6 miles. (Ref. 994768)

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

7 nights from £476

Last booked yesterday
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An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
33
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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

7 nights from £695

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The front exterior of a row of brick terraced houses with bay windows and small brick walls at Southview Retreat in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Attractive terraced house situated in Weymouth, wonderfully modernised. Off-road parking. WiFi. Beach 1 mile. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1010311)

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

7 nights from £722

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A small white house with a dark roof and black windows surrounded by potted plants and a gravel driveway with purple flowers in the foreground at Little England Cottage in Milborne St Andrew
Offer
19
Milborne St Andrew, Dorset, DT11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

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

A well-presented property resting on the outskirts of Milborne St Andrew. Pet-friendly. WiFi. Pub and shop within 0.4 miles. (Ref. 1017554)

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

  • 20% off - Sat 2nd Aug to 9th Aug 2025

  • 15% off - Sat 9th Aug to 16th Aug 2025

  • 10% off - Sat 16th Aug to 23rd Aug 2025

7 nights from £430

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A building with an outdoor seating area and garden at Overcombe Mill Nottington near Weymouth
47
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Overcombe Mill is a wonderful lodge nestled into the countryside of Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105455)

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

7 nights from £664

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The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
55
Weymouth, Dorset, DT4
  • Sleeps13
  • Bedrooms6
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

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

7 nights from £2014

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A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
30
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

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

7 nights from £566

Last booked yesterday
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A building exterior with benches and gardens at Corvesgate Nottington near Weymouth
52
Nottington near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.0★

    Good

  • Sykes rating

Corvesgate is a tasteful property resting in 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. 1105456)

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

7 nights from £633

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A rocky shoreline with a small beach a stone wall and garden plants at Weymouth Bay Apartment A in Weymouth
49
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

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

7 nights from £625

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A lighthouse and white buildings with a stone wall and grassy area at Old Higher Lighthouse Branscombe Lodge Portland Bill
40
Portland Bill, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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

7 nights from £620

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A wooden house with three dormer windows a gravel driveway and a fenced grassy area at The Donkey Shed in Sherborne
33
Sherborne, Dorset, DT9
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A wonderful detached property resting on the outskirts of Sherborne. WiFi. Ground-floor bedroom. Parking. Yeovil 8 miles. (Ref. 1003242)

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

7 nights from £730

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A house with a wooden door and windows next to a garden and trees at Tokenhill Cottage in Piddletrenthide
44
Piddletrenthide, Dorset, DT2
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

This well-presented three-bedroom property resides in Piddletrenthide, Dorset. Hot tub. Private garden. Off-road parking. In an AONB. Dorchester 8.9 miles. (Ref. 1130975)

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

7 nights from £871

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A dark wood cottage with a gravel driveway and potted plants at Belview Cottage Fifehead Neville near Sturminster Newton
35
Sturminster Newton, Dorset, DT10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

A detached, modern cottage in the quiet hamlet of Fifehead Neville. Within Blackmore Vale. Family-friendly. Enclosed garden. Lovely walks close by. Superb touring base. Sturminster Newton 3 miles. (Ref. 1357)

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

7 nights from £463

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A living room with two blue sofas a wooden coffee table a rug a TV a bookshelf and a fireplace at Ammonite Cottage Fortuneswell Portland
32
Fortuneswell Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Traditional Portland Cottage. Beautiful scenery walks. Close to pubs. (Ref. 993922)

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

7 nights from £515

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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

    4.7★

    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

7 nights from £713

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A white two-story house with four windows and a blue door surrounded by green grass and pink flowers
22
Bridport, Dorset, DT6
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A splendid, detached townhouse nestled between Bridport and West Bay in Dorset. Spacious. Dog-friendly. Family-friendly. Enclosed gardens. WiFi. Bridport 0.9 miles; West Bay 1 mile; Lyme Regis 10.3 miles; Axminster 12.8 miles. (Ref. 1106458)

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

7 nights from £1374

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A multi story residential building with large windows and a gravel driveway at Pointers View in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

A well-presented, upper-ground floor apartment set in a contemporary development in Weymouth, Dorset. Beach nearby. Adults only. Smart TV. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1123114)

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

7 nights from £627

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Two beige houses with black doors and windows on a paved street at Jurassic Coast House in Portland
Offer
42
Portland, Dorset, DT5
  • Sleeps8
  • Bedrooms4
  • PetsYes

    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)

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

  • 5% off - Sat 6th Sep to 20th Dec 2025

7 nights from £939

Last booked yesterday
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A patio with two chairs and a round metal table with a bottle and two glasses next to a white picket fence at High Bullen Cottage in Morcombelake
26
Morcombelake, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A cottage resting in Morcombelake, Dorset. Sea view. Close to a beach. Close to the town centre. Couples’ retreat. Charmouth 3 miles; Lyme Regis 5.8 miles; Beer 16.2 miles. (Ref. 1106067)

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

7 nights from £524

Last booked yesterday
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A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5★

    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)

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

7 nights from £567

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