Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 677 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Standby Generator Bunker, an impressive abode, rests in rural Ringstead in Dorset, enjoying sea views, a pet-friendly policy, and a woodburning stove. Dorchester 8.3 miles; Bridport 23.1 miles. (Ref. 1137374)

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

7 nights from £1005

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A detached barn conversion set within the village of Long Bredy. Woodburning fire. WiFi. Weymouth 12 miles; Yeovil 20 miles. (Ref. 998739)

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

7 nights from £493

  • Sleeps3
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Gold Gems Award Winner for Best on the South Coast 2023. A picturesque, reverse level Coach House settled in White Lackington near Piddletrenthide, Dorset. Private parking. Enclosed garden. Woodburning stove. Pet-free. Dorchester 6.7 miles. (Ref. 1087048)

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

7 nights from £633

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. Pet-friendly. WiFi. Enclosed garden. (Ref. 1008404)

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

7 nights from £521

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A lodge sleeping four people, Bowleaze area of Weymouth. Dog friendly. Large garden. Parking for two cars. (Ref. 994500)

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

7 nights from £645

Last booked 8 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from £604

  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

This pretty, detached cottage lies in Preston, Dorset. Smart TV. En-suite master bedroom. Close to amenities. Woodburning stove. Weymouth 3.6 mile. (Ref. 1119018)

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

7 nights from £645

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

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

7 nights from £521

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Perfect

  • Sykes rating

This beautifully-presented cottage rests in the village of Litton Cheney in Dorset. Near to village pub. Countryside views. Off-road parking. Dorchester 10.2 miles; Yeovil 21.1 miles. (Ref. 1021813)

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

7 nights from £648

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A Georgian, Grade II listed property resting in the charming town of Dorchester, Dorset. Historic features. Parking permits. Close to a pub and a shop. Weymouth 8.8 miles; Swanage 26.4 miles; Bournemouth 29.5 miles. (Ref. 1025833)

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

7 nights from £663

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A charming cottage based in the village of Wyke Regis, Dorset. Beach nearby. Dishwasher. Electric fire. Wifi. Weymouth 2.1 miles; Dorchester 9.7 miles. (Ref. 1121449)

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

7 nights from £635

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

Detached chalet bungalow in West Bexington, Dorset. Large garden with sea views. Close to beach. WiFi. Abbotsbury 4.8 miles; Bridport 6.8 miles. (Ref. 1017936)

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

7 nights from £1192

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Charming, modern barn located in the Dorset village of Bere Regis. WiFi. Close to shop and pub. Off-road parking. Courtyard garden. Wareham 6 miles. (Ref. 1000906)

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

7 nights from £500

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £599

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

A modern ground floor annex in Weymouth, just moments from the beach. 1 well behaved pet, WiFi, parking for two cars. (Ref. 994726)

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

7 nights from £714

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Old Post Office is a contemporary, four-bedroom home resting rurally in Glanvilles Wootton near Sherborne, Dorset. Pet-friendly. Hot tub. Rural views. Buckland Newton 2.8 miles; Cerne Abbas 5.7 miles; Sherborne 7.1 miles; Dorcesher 12.2 miles. (Ref. 1129395)

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

7 nights from £1419

  • Sleeps15
  • Bedrooms8
  • PetsYes

    4.8

    Outstanding

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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
  • £50 off - Sat 18th Oct to 25th Oct 2025

7 nights from £2348

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Link detached modern annex lodge in the Dorset Coastal village of Osmington. Wifi. Parking for two cars. Short drive to Weymouth. (Ref. 994794)

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

7 nights from £515

  • Sleeps8
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

7 nights from £983

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A delightful, semi-detached barn conversion resting in Notton, close to Maiden Newton in Dorset. Disabled friendly. Pet friendly. Jurassic coast nearby. Dorchester 7.1 miles; West Bay 15 miles. (Ref. 1096952)

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

7 nights from £729

 

Just show me Dorchester Cottages

 

If you're looking for somewhere with facilities on hand yet close to amazing countryside, our Dorchester cottages make great contenders. Think elegant architecture, historic sites, thriving culture and excellent shopping.

Dorchester's a fantastic place for browsing. Shoppers will find all kinds of specialist shops, high street names and markets, while museums range from dinosaurs, teddies and Chinese Terracotta Warriors, to Roman artefacts and Tutankhamun. And in between shopping and sightseeing, relish delicious snacks and meals in a wide variety of establishments, from pavement cafes to Michelin-starred restaurants.

When it comes to historic sites, Dorchester features a treasure trove of delights. Don't miss the splendid Roman Town House, the home of infamous 'Hanging' Judge Jeffreys, the huge Iron Age hill fort of Maiden Castle and the Roman amphitheatre at Maumbury Rings.

Thomas Hardy's Wessex a stone's throw from your Dorchester cottage

 

Dorset's wonderful landscapes have inspired many writers and most of Hardy's novels are based on Dorset; Dorchester is indeed the legendary town of 'Casterbridge'. The Dorset County Museum displays his works, while you can also visit his birthplace Hardy's Cottage and his Victorian villa Max Gate, designed by Hardy and built by his brother. Discover more of his beloved 'Wessex' on foot and stride out from your Dorchester cottage along the Dorchester to Weymouth Trail (10 miles).

To the west of the town centre you'll find Poundbury, Prince Charles' award-winning residential development built in the traditional architectural style of Dorchester and home to a variety of attractions, including a monthly farmers' market.

If you still haven't found what you're looking for there are plenty of other Dorset cottages to choose from.