Dorchester Cottage Holidays

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Dorchester Cottage Holidays

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Your Dorchester, Dorset search returned 687 cottages

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Map View
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★

    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


for 7 nights £532

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An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
21
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A pretty village lodge, close to the seaside town of Weymouth in Dorset. Traditional. Beautiful Mediterranean-style garden. WiFi. Dorset AONB. Dorchester 4.9 miles. (Ref. 1017591)

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


for 7 nights £385

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A row of brick terraced houses with bay windows and plants in front on a street at Seaside House in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Elegant end of terrace Georgian Townhouse located in Weymouth. Close to amenities. Off-road parking. Pet-free. Courtyard with furniture. Dorchester 7.2 miles; Bridport 20.5 miles. (Ref. 1071940)

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


for 7 nights £1180

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A garden with flowering plants and shrubs in front of a stone building with a tiled roof at Middle Farm Annex in Long Bredy
40
Long Bredy, Dorset, DT2
  • 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


for 7 nights £581

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Exterior view of a stone house with white framed windows a white garage door and a small porch at Fisherbridge Cottage Weymouth
39
Weymouth, Dorset, DT3
  • 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


for 7 nights £673

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A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
43
Dorchester, Dorset, DT2
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. On-site facilities. Family-friendly. Lakeside views. Woodburning stove. Puddletown 5.3 miles; Dorchester 5.6 miles; Weymouth 10 miles. (Ref. 1138508)

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


for 7 nights £810

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A small blue house with patio furniture and potted plants on a tiled patio at Outlook Lodge in Bowleaze
28
Bowleaze, Dorset, DT3
  • 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


for 7 nights £819

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A marina with boats and yachts docked and buildings in the background at Harbourside Haven Apartment 1 in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A superb first-floor apartment resting in Weymouth, Dorest. Stunning marina views. Allocated off-road parking. WiFi. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059262)

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


for 7 nights £636

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A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
44
Sutton Poyntz, Dorset, DT3
  • 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


for 7 nights £607

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A brick house with a sloped roof and skylights with a gravel driveway at Baytree Lodge in Osmington
59
Osmington, Dorset, DT3
  • Sleeps12
  • Bedrooms5
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Luxurious 5 star contemporary property. Games room. Indoor swimming pool. WiFi. Stunning views. Five en-suite bedrooms, one family bathroom. Large sitting room and generous sitting/dining room/kitchen. (Ref. 993982)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 7 nights £3550

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A stone house with a small porch table and chairs next to a gravel driveway surrounded by bushes at Glyde House in Dorchester
55
Dorchester, Dorset, DT1
  • Sleeps8
  • Bedrooms5
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Glyde House is a detached property situated in Dorchester, Dorset. Close to a shop and a pub. Off-road parking. Garden. Near Dorset AONB. Weymouth 8.6 miles; Isle of Portland 14.7 miles. (Ref. 1150284)

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


for 7 nights £1168

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A kitchen area with a wooden countertop with fruit bowl wine bottle and glasses a small dining table with a bench seat by a window and a bar stool seating area at The Coach House - Trinity Lodge in Godmanstone near Cerne Abbas
25
Godmanstone near Cerne Abbas, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Trinity Lodge is a striking rural holiday home with great attention to detail, within the Dorset National Landscape, in Goodmanstone, near Cerne Abbas. Dorchester 5.3 miles; Weymouth 14 miles; Sherborne 14.3 miles; Yeovil 17.4 miles. (Ref. 1149594)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights £431

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Stone buildings covered with greenery along a street with a white gate at Market House in Abbotsbury
43
Abbotsbury, Dorset, DT3
  • 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


for 7 nights £644

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A carport with gravel driveway and trees at The Halt in Maiden Newton
31
Maiden Newton, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles (Ref. 1165359)

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

  • 10% off - Wed 1st Apr to 30th Apr 2026


for 7 nights £357

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Two adjacent houses one with red brick facade and red door the other with cream facade and blue door on a street
26
Dorchester, Dorset, DT1
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    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


for 7 nights £622

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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★

    Outstanding

  • 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


for 7 nights £864

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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 £582

Last booked yesterday
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A brick building with multiple bay windows and doors along a street at The BoBo House in Weymouth
56
Weymouth, Dorset, DT4
  • Sleeps12
  • Bedrooms6
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

The BoBo House is a delightful terraced holiday home resting in the popular coastal town of Weymouth in Dorset set over four floors and near the beach. Dorchester 7 miles; Bridport 17 miles. (Ref. 1059621)

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


for 7 nights £1084

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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★

    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


for 7 nights £694

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A brick end terrace house with a white door and windows and a paved driveway at The Nightingale in Weymouth
33
Weymouth, Dorset, DT4
  • 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


for 7 nights £633

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Map View

Looking for somewhere to stay in the heart of Dorset? If so, then booking accommodation in Dorchester is a brilliant option to consider. With a mix of countryside charm and historic character, it’s the perfect spot for your next getaway.

Why Book Accommodation in Dorchester, Dorset?

Dorchester is a lovely market town found in the very centre of Dorset, steeped in history and full of character. As the county town, it’s known for its rich Roman heritage, with a range of fascinating attractions including the remains of a Roman townhouse and the town’s ancient walls.

Aside from its history, Dorchester also boasts a bustling town centre with shops, museums and a regular market that draws in locals and visitors alike. You’ll find plenty of great places to eat and drink here, from cosy pubs to charming cafés.

These Dorchester holiday homes also put you within easy reach of Dorset’s National Landscape boasting picturesque countryside and beautiful coastline. And with a train station resting in the middle of the town, you have easy access to many other pretty spots along the coast too.

So, whether you’re after relaxing walks, beach days, or simply a great location to unwind in, these cottages in Dorchester tick all the boxes.

Places to Visit from your Accommodation in Dorchester, Dorset

There’s plenty to see and do just a short drive from your accommodation in Dorchester, Dorset.

For a traditional seaside experience, take a 20-minute drive south to the coastal town of Weymouth. With its golden beach, charming promenade and bustling harbour, it’s a fantastic place for a family day out. If you have time, stop by Nothe Fort or take a stroll along the South West Coast Path for spectacular sea views. For those that wish to test their swing, be sure to check out one of the gold courses on the outskirts of the town.

Alternatively, visit the lovely village of Wool, also accessible by train. It's a great base for exploring the nearby Lulworth Cove and Durdle Door, two of the most iconic landmarks along the Jurassic Coast. Along the way, enjoy scenic drives through the Dorset countryside and stop off at local farm shops or cafés for a bite to eat.

For more ideas on what to do during your escape, be sure to check out this excellent Dorset Travel Guide.

Other Popular Destinations for booking Dorchester Holiday Homes:

Bournemouth

Poole

Swanage

Wareham

West Bay

Types of Dorset Holidays

As well as this fantastic selection of accommodation in Dorchester, there’s also a full collection of all Dorset holiday cottages to explore. If you're planning a large group getaway, these large cottages in Dorset are well worth a look.

Or, if you'd prefer to experience rural charm, don’t miss these farm cottages in Dorset or these log cabins in Dorset. Looking to stay close to the sea? Be sure to check out these coastal cottages in Dorset too.

Planning something extra-special? Then browse these luxury Dorset cottages or book one of these hot tub cottages in Dorset for added comfort.

There are also plenty of dog-friendly cottages in Dorset for those bringing their pooch along, or if you’re looking to escape soon, these last-minute cottages and short breaks in Dorset may be ideal.

Prefer something different? Then explore these unique glamping pods in Dorset or even a relaxing stay in one of these cottages with swimming pools. And for family fun, take a look at these family-friendly Dorset holidays too.