Weymouth Holiday Cottages

Your Weymouth, Dorset search returned 269 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published
Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
Offer
50
Brewers Quay Harbour, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.3★

    Good

  • Sykes rating

Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. Harbour views. Patio with furniture. Pubs and shop 5 mins. Beach 10 mins. Bridport 22 miles. (Ref. 994256)

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

  • 10% off - Wed 1st Jul to 31st Aug 2026


for 7 nights From £1364

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A two-story house with yellow brick facade and bay window with bushes in front at Amaranta Brewers Quay Harbour
33
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.3★

    Good

  • Sykes rating

A wonderful, newly renovated three-bedroom house resting in Weymouth, Dorset. Pet-friendly. Near a beach. Family-friendly. Enclosed patio. Dorchester 8.8 miles; Bridport 20.9 miles. (Ref. 1094065)

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


for 7 nights From £690

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A white brick exterior of two adjacent houses with black and green doors and windows at Wey Cottage in Weymouth
17
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.3★

    Good

  • Sykes rating

Traditional terraced cottage, 3 minutes' walk to the harbour, shop and café. WiFi. Pet-friendly. Enclosed courtyard garden. Dorchester 7 miles. (Ref. 998260)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From £449

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A beachfront with kayaks lined up near houses and water at Fairways in Wyke Regis
22
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

Fairways is a delightful house situated less than 2 mins walk to Smallmouth beach in Wyke Regis, Dorset, boasting an enclosed garden, Smart TV, and private driveway parking. Weymouth 2.5 miles; Dorchester 10.2 miles; Poole 34.1 miles. (Ref. 1047698)

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


for 7 nights From £608

Last booked 2 days ago
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A street view of terraced houses with one painted blue and windows and doors visible at Mackerel Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

Mackerel Cottage is a beautifully-designed, terrace cottage resting in the heart of Weymouth, Dorset. Woodburning stove. Pet-friendly. Near shop and pub. Dorchester 8.4 miles; Bridport 18.9 miles. (Ref. 1141828)

  • Pets go free
  • Wi-fi
  • Dishwasher


for 7 nights From £512

Last booked yesterday
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An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
22
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.2★

    Good

  • Sykes rating

Sea Spray is a pleasant, open-plan holiday home perched on the edge of Bowleaze, Dorset, enjoying sea views and a short walk to a beach and a pub. Weymouth 2.1 miles; Dorchester 6.8 miles; Yeovil 27.5 miles. (Ref. 1174075)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 7 nights From £536

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An exterior view of a house with pink and white windows at Seahorse Cottage in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3★

    Good

  • Sykes rating

Seahorse Cottage, a delightful stone terraced cottage near Old Harbour in Weymouth, Dorset, boasts a garden, a nearby beach and amenities, and allows pets. Dorchester 7 miles. (Ref. 1191297)

  • Pets go free
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £516

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A brick and white semi detached house with bay windows and potted plants outside at Anchor House Weymouth
Offer
68
Weymouth, Dorset, DT4
  • Sleeps15
  • Bedrooms6
  • Pet FriendlyYes

    4.6★

    Outstanding

  • Sykes rating

Anchor House is a stunning, pet-friendly townhouse with a private hot tub in the heart of Weymouth, Dorset, close to local amenities and the beach. Dorchester 7.8 miles; Bridport 19.9 miles. (Ref. 1105510)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

  • 15% off - Mon 13th Jul to 31st Dec 2026


for 7 nights From £1648

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An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
51
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.3★

    Good

  • Sykes rating

Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of accommodation with en-suite facilities and vaulted ceiling. Dog-friendly, plenty to see and do in the area. Weymouth 3.5 miles. (Ref. 932158)

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


for 7 nights From £604

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A brick residential building with white doors and windows next to a small lawn and paved driveway at Lodmoor House in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9★

    Outstanding

  • Sykes rating

A lovely two-bedroom house resting in Weymouth, Dorset. Family-friendly. Enclosed garden. Near a beach. Pet-friendly. Dorchester 6.7 miles; Bridport 19.6 miles. (Ref. 1120462)

  • Pets go free
  • Wi-fi
  • Washing machine


for 7 nights From £471

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A blue painted two storey building with bay windows and white doors with black railings in front at Harbour Watch Apartment 1 Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.2★

    Good

  • Sykes rating

A lovely apartment perfect for couples in Weymouth. Close to the town centre. Off-road parking for one car. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 8 miles. (Ref. 994289)

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


for 7 nights From £610

Last booked 2 days ago
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A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
24
Greenhill Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. Bedroom with en-suite. Off-road parking. Pet-friendly. Close to amenities. Close to beach. Dorchester 7 miles; Abbotsbury 9 miles; Bridport 19.9 miles. (Ref. 1093991)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £559

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A street with parked cars stone wall and houses overlooking the sea at Bowleaze View in Weymouth
30
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.3★

    Good

  • Sykes rating

Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)

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


for 7 nights From £878

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A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
23
Brewers Quay Harbour, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.5★

    Outstanding

  • Sykes rating

All second floor. Two bedrooms: 1 x double bed with en-suite shower, basin and WC, 1 x twin single. Bathroom with bath, basin and WC. Open plan living area with kitchen, dining area and sitting area. (Ref. 994293)

  • Wi-fi


for 7 nights From £659

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A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms3
  • Pet FriendlyNo

    4.7★

    Outstanding

  • Sykes rating

Three bedroom terraced property in central Weymouth. Open plan living area. (Ref. 1095056)

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


for 7 nights From £779

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Exterior view of a brick terraced house with blue door white window and small hedge at Leo's Place in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A well-presented property nestled in the heart of Weymouth, Dorset. Roadside parking. Enclosed patio. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1134491)

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


for 7 nights From £597

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A stone cottage with a white front door and a paved pathway bordered by trimmed hedges at Knapp Cottage in Chickerell
39
Chickerell, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

A charming, three-bedroom cottage sitting in Chickerell, Dorset. Close to amenities. Enclosed garden. Off-road parking. Weymouth 3.3 miles; Abbotsbury 5.9 miles; Portland 7.2 miles. (Ref. 1086432)

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


for 7 nights From £703

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A multi-story brick house with bay windows and greenery in front at The Lobster Pot in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

The Lobster Pot, a nicely-presented apartment rests in the gorgeous seaside town of Weymouth in Dorset. Open plan. En-suite. Close to beach and amenities. Dorchester 8.7 miles; Bridport 20.4 miles. (Ref. 1151706)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From £444

Last booked yesterday
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A living room with a sofa and coffee table at Sunrise Apartment in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.6★

    Outstanding

  • Sykes rating

A contemporary first-floor apartment overlooking the coast in Weymouth, Dorset. Open-plan. Sea views. WiFi. Close to amenities. Dorchester 7.4 miles; Bridport 20.2 miles. (Ref. 1097676)

  • Wi-fi


for 7 nights From £578

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An outdoor seating area with a table and chairs in front of a wooden house with a tiled roof and a small garden at Garland in Nottington near Weymouth
31
Nottington near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.4★

    Good

  • Sykes rating

Garland is a delightful abode resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105442)

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


for 7 nights From £576

Last booked yesterday
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