Weymouth Holiday Cottages

Your Weymouth, Dorset search returned 268 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
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
  • PetsYes

    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)

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


for 7 nights £559

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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
  • PetsNo

    4.4★

    Good

  • 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 £596

Last booked 2 days ago
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A living room with sofas and a television at Weyside in Weymouth
20
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7★

    Outstanding

  • Sykes rating

Weyside is a fantastic apartment in the seaside town of Weymouth, located in Dorset, boasting close proximity to the beach as well as several amenities. Dorchester 8.2 miles; Bridport 18.8 miles. (Ref. 1164944)

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


for 7 nights £659

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A living room with a beige sectional sofa and colorful cushions a wicker coffee table a small round white table with baked goods a lamp a chair with a pillow a dining area with wooden chairs and a table at Winkle Cottage in Weymouth
42
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

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


for 7 nights £615

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The front door and window of a brick house with plants growing around the entrance at 11 Beech Road Weymouth
43
Weymouth, Dorset, DT3
  • Sleeps7
  • Bedrooms4
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A spacious, semi-detached house resting in Weymouth, Dorset. Pet-friendly. Off-road parking. Open-plan. Bedroom with en-suite. Enclosed garden. Dorchester 4.7 miles; Bridport 17.2 miles. (Ref. 1105244)

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


for 7 nights £836

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A sandy beach with tire tracks and footprints beside a paved promenade with pedestrians and buildings at Sunrise Apartment in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    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 £686

Last booked yesterday
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A stone building with white framed windows and a door along a paved street in a residential area at Brewers Retreat in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.4★

    Good

  • Sykes rating

A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. Romantic. Near a beach. Pet-free. Close to amenities. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1114655)

  • Wi-fi
  • Washing machine


for 7 nights £556

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A brick terraced house with a green front door and front lawn at The Lookout -The House With A View in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

A well-presented, mid-terrace property resting within the village of Wyke Regis. Sea views. Pet-friendly. WiFi. Weymouth 2 miles; Dorchester 9 miles. (Ref. 1006910)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £677

Last booked yesterday
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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
  • PetsYes

    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)

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


for 7 nights £690

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An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
22
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1★

    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)

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


for 7 nights £554

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A living room with sofas a coffee table a fireplace a television and wall art at Victorian Town House in Weymouth
36
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms5
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

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


for 7 nights £653

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A living room with a blue sofa and television at Saddlers Cottage in Weymouth
Offer
17
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, two-bedroom home resting in Weymouth, Dorset. Close to amenities, attractions and beach. Pet-friendly. Near AONB. Enclosed small courtyard. Dorchester 7.5 miles; Bridport 19.2 miles. (Ref. 1132007)

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

  • £47 off - Sat 13th Jun to 20th Jun 2026


for 7 nights £397

Last booked yesterday
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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
  • PetsNo

    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 £659

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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
  • PetsYes

    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)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £531

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A living room with two sofas a coffee table a TV and paintings on the wall at Harbour Watch 2 in Weymouth
Offer
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

Located on the harbourside, is this two-bedroom contemporary apartment in Weymouth, Dorset. WiFi. Fortuneswell 4.7 miles; Dorchester 9.3 miles. (Ref. 1017563)

  • Ground floor bedroom
  • Dishwasher
  • Washing machine

  • 10% off - Fri 17th Apr to 25th Jul 2026


for 7 nights £831

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A stone house with a tiled roof and a paved driveway at Sunningdale Rise in Preston
46
Preston, Dorset, DT3
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Sunningdale Rise is a striking, detached home on a gated development with off-road parking, close to a beach, in the village of Preston in Dorset. Weymouth 2.5 miles. (Ref. 1149947)

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


for 7 nights £1362

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A deck with chairs and a door at Chesil Beach Holiday Park - Holiday Accommodation 16933, Weymouth
12

Holiday Park

Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms2
  • PetsNo

  • Sykes rating

2x Bedroom Holiday Home at Chesil Beach Holiday Park with Veranda and Sea Views over the Beautiful Jurassic Coast in Dorset. (Ref. 1186144)

  • Wi-fi
  • Swimming pool


for 7 nights £556

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A white semi detached house with blue doors and a blue fence under a clear sky at Ashwood Brewers Quay Harbour
22
Brewers Quay Harbour, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4★

    Good

  • Sykes rating

Modern 3 Storey house. Close to the Harbour, Newton’s Cove and Brewers Quay. WIFI. Parking for one car. 5 minutes to local shop. 15 minute walk to town centre. (Ref. 993939)

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


for 7 nights £786

Last booked yesterday
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A house with windows and a pathway at 1 Fernhill Avenue Weymouth
62
Weymouth, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • 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 £1047

Last booked yesterday
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A brick apartment building with balconies and parking at Brewery View in Weymouth
22
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Brewery View is a stylish, first-floor apartment near the beach in Weymouth, Dorset, with an open-plan living space, balcony, and designated parking. Dorchester 8.8 miles; Bridport 19.4 miles. (Ref. 1189426)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £522

Last booked yesterday
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