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Dorchester Cottage Holidays

Your Dorchester, Dorset search returned 677 cottages

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Map View

A wooden house with skylights and a small garden area surrounded by trees at Roman Lodge in Osmington

Roman Lodge Save

Osmington, Dorset, DT3

Sleeps6
Bedrooms3
PetsYes

4.5★

Outstanding

Sykes rating

A bright and airy lodge resting in Osmington near Preston, Dorset. Open-plan. Close to beach. Pet-friendly. Weymouth 5.4 miles; Poole 23.4 miles; Bournemouth 29.1 miles. (Ref. 1093891)

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

for 7 nights £720

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An exterior view of Wren Cottage in Weymouth

Wren Cottage Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsYes

4.9★

Outstanding

Sykes rating

An inviting, mid-terrace house perched on the coast in Weymouth, Dorset. Sea views. Off-road parking. Near the beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1082718)

Wi-fi
Washing machine
Baby-friendly

for 7 nights £447

Last booked yesterday

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Travel plans can change

Choose our "Flexible" booking option and cancel at least a week before your check-in date to get a refund (exclusions apply).

Find out more. T&Cs apply

A building with balconies and stairs in front with a palm tree on the side at Lookout in Cove Castle

Lookout Save

Cove Castle, Dorset, DT4

Sleeps4
Bedrooms2
PetsYes

4.8★

Outstanding

Sykes rating

Comfortable Spanish style holiday home in Weymouth. Off road parking for two cars. Patio garden with furniture. Sea views. Beach 5 min. Pub and shop 10 min. Dorchester 9 miles. (Ref. 994352)

Wi-fi
Off-road parking
Dishwasher
Washing machine

for 7 nights £690

Last booked yesterday

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Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth

Maisy Cottage Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsNo

4.7★

Outstanding

Sykes rating

Modern and beautiful cottage in the heart of Weymouth. Close to town centre. Wifi. Parking for two cars. Landscaped garden with patio. Shop and pub 5 min. Bridport 22.5 miles. (Ref. 994369)

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

for 7 nights £581

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Front view of three terraced houses with plants and bushes in front at Kingfisher Cottage in Weymouth

Kingfisher Cottage Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsNo

4.9★

Outstanding

Sykes rating

A terrace property resting close to the beach and harbour in Weymouth. Allocated parking for two cars. WiFi. Fortuneswell 4.7 miles; Dorchester 8.9 miles. (Ref. 1038344)

Wi-fi
Off-road parking
Dishwasher
Washing machine

for 7 nights £504

Last booked yesterday

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A balcony with a table and chairs overlooking a garden and sea at The View in Weymouth

The View Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsYes

5.0★

Perfect

Sykes rating

The View is a charming, three-storey house resting near the beach in Weymouth, Dorset, boasting stunning sea views, a balcony, and off-road parking. Dorchester 8.9 miles; Bridport 19.2 miles. (Ref. 1173086)

Wi-fi
Off-road parking
Dishwasher
Washing machine

for 7 nights £681

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A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour

Mermaid House Save

Brewers Quay Harbour, Dorset, DT4

Sleeps5
Bedrooms3
PetsNo

4.8★

Outstanding

Sykes rating

This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. Close to amenities and harbour. Pet-free. Garden. Dorchester 8.7 miles; West Lulworth 15.8 miles. (Ref. 1093760)

Wi-fi
Off-road parking
Washing machine

for 7 nights £670

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Travel plans can change

Choose our "Flexible" booking option and cancel at least a week before your check-in date to get a refund (exclusions apply).

Find out more. T&Cs apply

A street view of terraced houses with white doors and windows at Angel Cottage in Weymouth

Angel Cottage Save

Weymouth, Dorset, DT4

Sleeps2
Bedrooms1
PetsNo

4.6★

Outstanding

Sykes rating

A characterful one-bedroom property resting in Weymouth, Dorset. Close to amenities and a beach. Near an AONB. Couples retreat. Dorchester 6.8 miles; Bridport 18.3 miles. (Ref. 1125691)

Wi-fi

for 7 nights £320

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A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth

The Nook Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsYes

4.5★

Outstanding

Sykes rating

The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. Dorchester 8.5 miles; Bridport 20.5 miles; Poole 32.2 miles. (Ref. 1107935)

Wi-fi
Off-road parking
Dishwasher
Washing machine

for 7 nights £607

Last booked yesterday

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An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth

Fountain Cottage Save

Weymouth, Dorset, DT4

Sleeps2
Bedrooms1
PetsNo

4.7★

Outstanding

Sykes rating

A cosy stone cottage for two this is the ideal place to spend quality time together, walking and exploring the local area. (Ref. 994208)

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

for 7 nights £511

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Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown

Miller's Cottage Save

Puddletown, Dorset, DT2

Sleeps2
Bedrooms1
PetsYes

4.7★

Outstanding

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

for 7 nights £418

Last booked yesterday

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The exterior wall of a yellow building with a white door and window and potted plants along the wall at Cuckoo Cottage in Bridport

Cuckoo Cottage Save

Bridport, Dorset, DT6

Sleeps2
Bedrooms1
PetsNo

4.9★

Outstanding

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

for 7 nights £415

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Stone cottage with thatched roof and white door with windows at Laurel Cottage in Osmington

Laurel Cottage Save

Osmington, Dorset, DT3

Sleeps3
Bedrooms2
PetsYes

4.1★

Good

Sykes rating

A charming thatched roof character cottage resting in the village of Osmington, Dorset. Off-road parking. Open-plan living. WiFi. Close to pub. Weymouth 4.4 miles; Dorchester 5.4 miles. (Ref. 1064960)

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

for 7 nights £494

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A living room with sofas and a fireplace at Otter Cottage in Weymouth

Otter Cottage Save

Weymouth, Dorset, DT4

Sleeps6
Bedrooms3
PetsYes

5.0★

Perfect

Sykes rating

A boutique, period home moments from Weymouth's iconic harbour. Dorchester 8.3 miles; Bridport 18.9 miles (Ref. 1177943)

Wi-fi
Dishwasher
Washing machine
Baby-friendly

for 7 nights £692

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Travel plans can change

Choose our "Flexible" booking option and cancel at least a week before your check-in date to get a refund (exclusions apply).

Find out more. T&Cs apply

Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth

Old Coastguard Apartment 2 Save

Weymouth, Dorset, DT4

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

15% off - Mon 23rd Feb to 2nd Apr 2026

for 7 nights £1006

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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

Tiddlers Cottage Save

Uploders near Bridport, Dorset, DT6

Sleeps2
Bedrooms1
PetsNo

5.0★

Perfect

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

for 7 nights £408

Last booked 8 hours ago

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The exterior of a brick house with a tiled roof a black door a paved path and plants at Badbury Lodge Brewers Quay Harbour

Badbury Lodge Save

Brewers Quay Harbour, Dorset, DT4

Sleeps4
Bedrooms2
PetsNo

4.6★

Outstanding

Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

Wi-fi
Washing machine
Baby-friendly

for 7 nights £529

Last booked yesterday

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A house with windows and a pathway at 1 Fernhill Avenue Weymouth

Greenwell Save

Weymouth, Dorset, DT4

Sleeps8
Bedrooms4
PetsNo

Sykes rating

Greenwell, a delightful house located in the town of Weymouth in Dorset boasting a Smart TV, woodburning stove and proximity to the beach and pub. Dorchester 7 miles; Bridport 17 miles. (Ref. 1128598)

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

for 7 nights £1020

Last booked yesterday

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A marina with boats docked and buildings in the background at Harbourside Haven Apartment 2 in Weymouth

Harbourside Haven Apartment 2 Save

Weymouth, Dorset, DT4

Sleeps4
Bedrooms2
PetsNo

4.6★

Outstanding

Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)