Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 256 cottages

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A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
29
Preston, Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

This delightful, two-bedroom bungalow rests in Preston, Dorset. Ground-floor living. Enclosed garden. Near an AONB. Weymouth 3.5 miles. (Ref. 1126160)

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


for 7 nights $786

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A brick terraced house with a white front door gravel front garden and small plants at Home Waters in Wyke Regis
23
Wyke Regis, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Off road parking. Sleeping 6 close to Portland marina. Dog friendly. (Ref. 994270)

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


for 7 nights $765

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The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. En-suite master bedroom. Beach 1 mile. Dorchester 9 miles. (Ref. 994201)

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

  • $468 off - Mon 22nd Dec to 29th Dec 2025

  • $460 off - Mon 29th Dec 2025 to 5th Jan 2026


for 7 nights $900

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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
  • PetsNo

    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 $1014

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A row of terraced houses with different colored facades along a street at Old Harbour Townhouse in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. Near coast. Woodburning stove. Open-plan. Near pub. Dorchester 8.7 miles; Bridport 19.4 miles. (Ref. 1159836)

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


for 7 nights $896

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A house with outdoor seating area at Budmouth Upwey near Weymouth
42
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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


for 7 nights $805

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Front view of a brick house with decorated windows and a black door with red steps and a driveway at Gone Fishing in Brewers Quay Harbour
32
Brewers Quay Harbour, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

Four bedroom semi-detached property in Weymouth. WiFi. Off road parking two cars. Large patio. (Ref. 994226)

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


for 7 nights $1259

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A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
24
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5★

    Outstanding

  • Sykes rating

A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. Excellent location. Smart TV. WiFi. Dorchester 7.4 miles; Bridport 18.8 miles. (Ref. 1123724)

  • Wi-fi


for 7 nights $720

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A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
55
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. Smart TV. Pet-friendly. Sea views. Close to amenities. Dorchester 7.9 miles; Bridport 20.6 miles. (Ref. 1118900)

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


for 7 nights $1792

Last booked 2 days ago
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Front of a white building with black door and window frames flowers in front at Harbour Reach Brewers Quay Harbour
36
Brewers Quay Harbour, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Stylish fisherman’s cottage just a few minutes’ walk from Old Harbour in Weymouth. Beach 1 mile. Harbour, shop and pub 5 min. Welcomes one dog. Poole 33 miles. (Ref. 1058438)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $801

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An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
33
Upwey near Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)

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


for 7 nights $892

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An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2★

    Good

  • Sykes rating

A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1111030)

  • Wi-fi
  • Dishwasher


for 7 nights $809

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A brick terraced house with a black front door two windows with shutters and a street lamp in front at Harbour Catch Cottage in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Traditional cute cottage, in the town centre side of Weymouth harbour. WIFI, Close to Shops, restaurants and bars. Perfect for a couples retreat. (Ref. 994240)

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


for 7 nights $650

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A living room with leather sofas glass coffee table and large windows overlooking a marina at Harbourside Haven Penthouse 1 in Weymouth
16
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

An immaculate penthouse apartment resting in the centre of Weymouth, Dorset. WiFi. Views over the marina. Off-road parking. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059266)

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


for 7 nights $779

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A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly


for 7 nights $706

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A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. Ground-floor living. Near to shop and pub. En-suite. Dorchester 8.5 miles; Bridport 17.5 miles. (Ref. 1152691)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom


for 7 nights $892

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A brick house with white framed windows a pale green door and parking signs outside at Anchor Cottage in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Anchor Cottage is a delightful, terraced home resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Family-friendly. Dorchester 7.6 miles; West Bay 17.8 miles. (Ref. 1150151)

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


for 7 nights $708

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A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. Near Dorset AONB. Sea views. Close to amenities and a beach. Private balcony. Off road parking. Dorchester 7.3 miles; Bridport 18.9 miles. (Ref. 1133961)

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


for 7 nights $675

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A row of terraced houses with stairs leading to the front doors and balconies above on a clear day at Wessex View in Weymouth
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.3★

    Good

  • Sykes rating

This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. Sea views. Elegant décor. Close to amenities. Dorchester 7.5 miles; Bridport 19.4 miles. (Ref. 1034440)

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


for 7 nights $815

Last booked 6 hours ago
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A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A homely, mid-terrace cottage based in Weymouth. Enclosed decking. Smart TV. Beach nearby. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1094925)

  • Wi-fi
  • Off-road parking
  • Baby-friendly


for 7 nights $640

Last booked yesterday
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