Dorchester Cottage Holidays

British Travel Award Winners!
We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.
Your Dorchester, Dorset search returned 681 cottages
- Sleeps3
- Bedrooms2
- PetsNo
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 £683
- Sleeps2
- Bedrooms1
- PetsNo
A stylish and contemporary apartment set in the town of Weymouth, Dorset. Seaside setting. Fantastic views. Off-road parking. Fortuneswell 5.8 miles; Dorchester 7.2 miles; Bridport 20.9 miles. (Ref. 1072234)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £714
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps2
- Bedrooms1
- PetsNo
A romantic pied-a-terre in the bustling market town of Bridport. Close to the Jurassic Coast. Parking. WiFi. Open-plan living. (Ref. 1004940)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £415
- Sleeps2
- Bedrooms1
- PetsNo
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
7 nights from £476
- Sleeps2
- Bedrooms1
- PetsNo
This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. Enclosed garden. Romantic. In an AONB. Close to amenities. West Bay 5 miles; Lyme Regis 14.1 miles. (Ref. 1117867)
- Wi-fi
- Off-road parking
- Washing machine
7 nights from £403
- Sleeps2
- Bedrooms1
- PetsNo
A delightful, one-bedroom holiday home resting in Weymouth, Dorset. Contemporary. Private garden. Romantic. Close to amenities and beach. Near AONB. Open-plan. Dorchester 7 miles; Bridport 20.8 miles. (Ref. 1133982)
- Wi-fi
- Off-road parking
7 nights from £500
- Sleeps2
- Bedrooms1
- PetsNo
A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £476
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps2
- Bedrooms1
- PetsNo
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 £874
- Sleeps2
- Bedrooms1
- PetsYes
A quaint stone-built cottage resting on the outskirts of Weymouth. Open-plan living. Off-road parking. WiFi. Dorchester 6.4 miles; Fortuneswell 8.2 miles. (Ref. 1061544)
- Wi-fi
- Off-road parking
- Electric vehicle charging
- Ground floor bedroom
- Washing machine
7 nights from £534
- Sleeps2
- Bedrooms1
- PetsYes
Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. Dorchester 5.5 miles. (Ref. 1160443)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £463
- Sleeps2
- Bedrooms1
- PetsYes
An attractive end-terrace cottage found in the peaceful Dorset village of Winterborne Kingston. Ideal for couples. Private parking. Pet friendly. Blandford Forum 6.5 miles; Poole 14.2 miles; Bournemouth 18.5 miles. (Ref. 1075037)
- Wi-fi
- Off-road parking
- Washing machine
7 nights from £461
- Sleeps2
- Bedrooms1
- PetsYes
Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £494
- Sleeps2
- Bedrooms1
- PetsYes
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
7 nights from £466
- Sleeps4
- Bedrooms2
- PetsYes
Stylish renovated ground floor apartment in Weymouth. Town centre a short walk away. WiFi. Welcomes one dog. Pub and shop 5 min. Beach 10 min. Dorchester 8.3 miles. (Ref. 994763)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £638
Travel plans can change
Choose our 'Flexible' booking option and cancel by 12 noon on your check-in day to get a refund (exclusions apply).
- Sleeps4
- Bedrooms2
- PetsYes
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
- Sleeps4
- Bedrooms2
- PetsYes
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 £649
- Sleeps4
- Bedrooms2
- PetsYes
This quirky, converted bunker rests in Ringstead near Preston, Dorset. Open fire. In an AONB. Smart TV. Off-road parking. Weymouth 7.6 mile. (Ref. 1131689)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
7 nights from £824
- Sleeps4
- Bedrooms2
- PetsYes
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 £567
- Sleeps4
- Bedrooms2
- PetsYes
A boutique, two-bedroom property situated in Brewers Quay Harbour, Weymouth, Dorset. Quality finish. Sea and harbour views. Enclosed garden. Raised elevation. Dorchester 8.5 miles; West Lulworth 15.5 miles. (Ref. 1096352)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £904
- Sleeps4
- Bedrooms2
- PetsYes
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 £1062
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.