Weekend Breaks in Weymouth

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Your Weymouth, Dorset search returned 321 cottages

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Exterior view of a multi-story building with beige brick walls and blue glass balconies at Nautica in Weymouth
15
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.4★

  • Sykes rating

A contemporary second-floor apartment set within the town of Weymouth, Dorset. Close to the close. Balcony with views. Dorchester 8.4 miles; Bridport 19.2 miles; Bournemouth 37.1 miles. (Ref. 1052595)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights $660

Last booked yesterday
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A living room with a sofa and dining table at Vista Mare 2 in Weymouth
25
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Vista Mare 2 is a lovely apartment perched in the heart of Weymouth, a popular town in Dorset, enjoying fantastic sea views from the open-plan living space. Dorchester 7.5 miles; Bridport 21.1 miles. (Ref. 1164686)

  • Wi-fi
  • Dishwasher


for 3 nights $868

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A stone house with wooden doors and windows along a road with slow painted on the street at Wren in Upwey
36
Upwey, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Wren, a stylish, two-bedroom home rests in Upwey, Dorset. Near AONB. Close to amenities. Near the beach and attractions. Enclosed garden. Contemporary. Weymouth 4.2 miles; Dorchester 4.4 miles. (Ref. 1138702)

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


for 3 nights $694

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An outdoor view of a cottage with a thatched roof and stone wall at Bracken Cottage in
Offer
11
Osmington, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Bracken Cottage is a romantic property resting in the village of Osmington, Dorset, boasting an open-plan living area, is close to the beach and amenities. Weymouth 5.4 miles. (Ref. 1173628)

  • Wi-fi
  • Off-road parking

  • 10% off - Mon 12th Jan to 31st Dec 2026


for 3 nights $609

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A living room with a television on a cabinet at Arum in Portland Bill
32
Easton, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Arum is a single-storey bungalow resting in Wakeham, Portland, with off-road parking, Smart TV, and a small patio. Portland 0.3 miles; Weymouth 6.9 miles; Dorchester 14.1 miles. (Ref. 1183330)

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


for 3 nights $643

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A living room with a sofa and dining area at Betty's Buoy Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Betty’s Buoy is a stylish first-floor apartment in Weymouth, Dorset, with open-plan living and easy access to the beach. Dorchester 7.5 miles; Bridport 18.8 miles. (Ref. 1168986)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights $571

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A living room with a fireplace and kitchen visible at Fisherman’s Cottage
27
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Fisherman’s Cottage, a pleasant house nestled in Weymouth, Dorset, with an open-plan design, an enclosed courtyard and proximity to the beach and amenities. Dorchester 8.4 miles; Bridport 19 miles. (Ref. 1172825)

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


for 3 nights $579

Last booked yesterday
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A living room with a staircase and a sofa at Harbourside in Weymouth
New property
34
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Harbourside is a charming, dog-friendly, Grade II listed house in Weymouth, Dorset, set over three stories, with open-plan living and a private courtyard. Dorchester 8.8 miles; Bridport 18.9 miles. (Ref. 1172365)

  • Wi-fi
  • Washing machine


for 3 nights $504

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A cottage with a patio and chairs at Bubbs Cottage
39
Winfrith Newburgh, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

Bubbs Cottage is a charming thatched cottage near Winfrith Newburgh, Dorset, boasting proximity to the Jurassic Coast, WiFi, a garden and allows pets. Dorchester 9 miles; Wareham 8 miles. (Ref. 1183195)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights $701

Last booked yesterday
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The Old Post Office - 1127439 - photo 1
33
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

The Old Post Office, a stylish pet-friendly house nestled in the town Weymouth, Dorset, features a Smart TV, proximity to the beach and marina. Dorchester 8.5 miles; Bridport 20.5 miles. (Ref. 1127439)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights $699

Last booked yesterday
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Harbour Reach 7 - 1194446 - photo 1
New property
26
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Harbour Reach 7, an agreeable second-floor apartment in the town of Weymouth, in Dorset, boasts proximity to the beach, shop and pub and West Dorset Heritage Coast. Dorchester 7.9 miles; Bridport 18.5 miles. (Ref. 1194446)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights $751

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An exterior view of a house with steps and a blue door at Corner Cottage in Preston
Offer
31
Weymouth, Dorset, DT3
  • Sleeps5
  • Bedrooms3
  • PetsNo

  • Sykes rating

Ash Corner Cottage is a lovely house in Preston near Weymouth Dorset, with sea views from the bedrooms, an enclosed multi-level garden and is a 20 minute walk or short drive to the beach. Weymouth 3.8 miles. (Ref. 1176572)

  • Wi-fi
  • Off-road parking
  • Dishwasher

  • 5% off - Wed 25th Mar to 18th Jul 2026


for 3 nights $798

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The front door of a blue and white house with two blue pots containing plants and a blue wooden planter in front at Cove Cottage Hideaway in Chiswell On Portland
36
Chiswell On Portland, Dorset, DT5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    3.3★

  • Sykes rating

Cove Cottage Hideaway is a romantic, terrace abode near the coast in Chiswell on Portland, Dorset. Close to amenities and beach. Sea Views. Romantic. Weymouth 5.2 miles. (Ref. 1150238)

  • Wi-fi


for 3 nights $649

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An outdoor area with a house and kayaks by the water at Still Waters in Weymouth
New property
42
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

  • Sykes rating

Still Waters is a fine three-storey house in Weymouth, Dorset, offering sea views, off-road parking, a courtyard, and open-plan living. Dorchester 10.6 miles; Bridport 18.8 miles. (Ref. 1195851)

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


for 3 nights $1053

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Two small wooden cabins in a grassy area with trees and outdoor wooden table and chairs with red flowers at Fallow in Warmwell
22
Warmwell, Dorset, DT2
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Fallow is a superb hut near Broadmayne, Dorset, boasting impressive countryside views to admire with the fire pit in the garden and a woodburning stove. Dorchester 5.8 miles; Weymouth 8.2 miles; Bridport 20.6 miles; Swanage 21 miles. (Ref. 1174455)

  • Off-road parking
  • Ground floor bedroom


for 3 nights $397

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A front entrance with a blue door and window at 23 The Maltings in Weymouth
New property
23
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Dolphin Cottage is a lovely cottage nestled into the bustling seaside town of Weymouth, Dorset, close to a shop, pub, local walks, and beaches. Fortuneswell 4.8 miles; Dorchester 8.9 miles; Bridport 19.5 miles. (Ref. 1179916)

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


for 3 nights $877

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An exterior of a property showcasing a door and windows at 46 Chafeys Avenue
New property
45
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

  • Sykes rating

Wilkie's Place is a welcoming, pet-friendly house near the beach in Weymouth, Dorset, featuring a conservatory and an enclosed, multi-tiered garden. Dorchester 7.5 miles; Bridport 18.8 miles. (Ref. 1196651)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 3 nights $1036

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A red brick house with a front garden at Home from Home near the Sea Weymouth
New property
40
Wyke Regis, Dorset, DT4
  • Sleeps8
  • Bedrooms4
  • PetsNo

  • Sykes rating

Home from Home near the Sea is a neat three-storey house resting in Wyke Regis, Dorset, featuring easy access to the beach and nearby local amenities. Weymouth 2.8 miles; Dorchester 10.2 miles. (Ref. 1200131)

  • Wi-fi
  • Off-road parking
  • Dishwasher


for 3 nights $1184

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A house with white facade and windows at NO 10 Fortuneswell
New property
34
Fortuneswell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

  • Sykes rating

NO 10 is a fine, dog-friendly house situated in Fortuneswell, Dorset, featuring an electric fire, an enclosed courtyard, and easy access to the beach. Weymouth 5.1 miles. (Ref. 1200066)

  • Wi-fi
  • Dishwasher


for 3 nights $825

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An outdoor area with a brick exterior and a purple bench at Amber House in Dorchester
New property
27
Dorchester, Dorset, DT1
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Amber House is a pleasant reverse-level house in Dorchester, Dorset, featuring open-plan living, a private courtyard, and off-road parking for one car. Weymouth 9.7 miles. (Ref. 1199636)

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


for 3 nights $614

Last booked 2 hours ago
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