Dorchester Cottage Holidays

Within 20 miles
  • Within 1 mile
  • Within 2 miles
  • Within 3 miles
  • Within 5 miles
  • Within 10 miles
  • Within 20 miles
  • Within 30 miles
  • Within 50 miles
1
2
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
0
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
Pets
  • Pets
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • Property pet free
7
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
3 Days +/-
  • Exact Dates
  • 1 Day +/-
  • 2 Days +/-
  • 3 Days +/-
Our most popular properties are filling up fast!

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.

Dorchester Cottage Holidays

REFINE SEARCH

Your Dorchester, Dorset search returned 683 cottages

Most relevant
  • Distance to Location
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Tick Rating (lowest first)
  • Tick Rating (highest first)
20
  • 10
  • 20
  • 50
  • 100
Map View
A stone and brick house with arched windows a green door a bench and gravel driveway at The Coach House at Lackington Farm in Piddletrenthide
57
Piddletrenthide, Dorset, DT2
  • Sleeps3
  • Bedrooms2
  • PetsNo

    5.0

    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 £683

See more details
A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour
42
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

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

See more details
The exterior wall of a yellow building with a white door and window and potted plants along the wall at Cuckoo Cottage in Bridport
19
Bridport, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

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

See more details
A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth
25
Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

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

See more details
A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport
45
Uploders near Bridport, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

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

See more details
A stone cottage with two windows a door and potted plants on a gravel yard with stone steps and greenery at Mill Cottage in Upwey
30
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    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 £874

Last booked 2 days ago
See more details
A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

Beautiful seafront apartment within the popular resort of Weymouth in Dorset. Incredible sea views. WiFi. Centre of Weymouth. (Ref. 1003083)

  • Wi-fi
  • Dishwasher

7 nights from £498

See more details
A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
18
Upwey, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Sykes Rating

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

See more details
Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown
27
Puddletown, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

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

Last booked 2 days ago
See more details
A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
24
Brewers Quay Harbour, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

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

See more details
A cottage with a thatched roof and red door next to another house with a driveway and parked car at Cosynook Cottage in Winterborne Kingston
23
Winterborne Kingston, Dorset, DT11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

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

See more details
A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth
26
Nottington near Weymouth, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

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

See more details
A single story white building with a grey roof and glass entrance surrounded by a wooden fence at Cliff Barn in Burton Bradstock
27
Burton Bradstock, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

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

See more details
A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock
17
Burton Bradstock, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

A brightly decorated property resting within the village of Burton Bradstock. Pet-friendly. WiFi. Pub and shop within 0.2 miles. Weymouth 15.7 miles. (Ref. 1008498)

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

7 nights from £520

See more details
A single-story building with mixed stone and brick walls a green door and multiple windows beside a gravel pathway and picnic table at Hebe in Notton near Maiden Newton
34
Notton near Maiden Newton, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A delightful, two-bedroom barn conversion resting in Notton, Dorset. Disabled-friendly. Dog-friendly. Eco-friendly. Enclosed garden. West Bay 15 miles; Weymouth 16.2 miles; Lyme Regis 24 miles. (Ref. 1096950)

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

7 nights from £719

See more details
A white cottage with a garden and wooden archway surrounded by a fence at Willowbrook Cottage in Litton Cheney
28
Litton Cheney, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    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 £685

See more details
A garden with plants and flowers next to a patio with lounge chairs and a table under an umbrella at Meadows End in Owermoigne Nr Broadmayne
36
Owermoigne Nr Broadmayne, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Meadow’s End is a delightful, detached cottage, with a toasty woodburning stove, located in the pretty Dorset village of Owermoigne, welcoming pets. Dorchester 6.8 miles; Weymouth 8.6 miles; Swanage 20.3 miles; Bridport 21.7 miles. (Ref. 1162476)

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

7 nights from £1007

See more details
An outdoor dining area with a table and six chairs set in front of a bunker entrance with grass on the roof at The Transmitter Bunker in Ringstead
33
Ringstead, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

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

See more details
A living room with a brown leather sofa blue armchair glass coffee table and television at Tides Corner in Bowleaze
36
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

See more details
A corner of a living room with a bay window showing a view outside and a TV on a white cabinet at Waterside in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

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

See more details
Map View

 

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.