Weymouth Holiday Cottages

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Your Weymouth, Dorset search returned 259 cottages

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The exterior of a two story house with a balcony and tiled roof at Bayview Overcombe near Preston
19
Overcombe near Preston, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

Bayview is a lovely first-floor apartment in Overcombe, near Preston, in Dorset, welcoming a pet and boasting stunning beach views from a balcony. Weymouth 2.1 miles. (Ref. 1159732)

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


for 7 nights $829

Last booked yesterday
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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A stone walkway with plants along the side of a stone house at The Apple Loft at Jordan House in Preston
21
Preston, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.2★

    Good

  • Sykes rating

The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. Off-road parking. Open-plan. Garden. Dorchester 6.1 miles; Abbotsbury 9.8 miles; Bridport 19.3 miles. (Ref. 1149531)

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


for 7 nights $709

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
22
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    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)

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


for 7 nights $751

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A row of brick houses with blue and turquoise front doors and white windows on a street at Chapelhay Cottage in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. Close shop and a pub. Close to a beach. Jurassic Coast. Portland 5.9 miles; Dorchester 8.4 miles; Lyme Regis 28.3 miles. (Ref. 1131030)

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


for 7 nights $852

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A dining area with a long table set with plates glasses and bread surrounded by blue chairs and a kitchen with appliances and plants at Beachaven in Weymouth
48
Weymouth, Dorset, DT4
  • Sleeps15
  • Bedrooms7
  • PetsNo

  • Sykes rating

Beachaven is a charming holiday home, set over three floors, located in the popular resort of Weymouth in Dorset resting near the beach and amenities. Dorchester 7.6 miles; Bridport 19.2 miles. (Ref. 1151664)

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

  • 5% off - Fri 27th Mar to 3rd Apr 2026

  • 5% off - Fri 10th Apr to 17th Apr 2026


for 7 nights $1947

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A street with parked cars stone wall and houses overlooking the sea at Bowleaze View in Weymouth
30
Weymouth, Dorset, DT3
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    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 $1238

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
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
  • PetsNo

    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 $970

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A window with binoculars on the sill looking out to buildings a clock tower and a marina at Anchorage View in Weymouth
30
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Anchorage View is a stunning, two-bedroom property resting in Weymouth, Dorset. Pretty views. Near the Dorset AONB. Close to amenities and a beach. Dorchester 8.5 miles; Bridport 19 miles. (Ref. 1145912)

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


for 7 nights $789

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A living room with two blue sofas and a wooden coffee table next to a fireplace and dining area in the background at Day Cottage in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

A delightful, terraced cottage nestled into the coastal town of Weymouth, Dorset. Open-plan living. Near amenities and beach. Close to attractions. Pet-friendly. Dorchester 8.4 miles; West Bay 18 miles; Lyme Regis 32.6 miles. (Ref. 1124105)

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


for 7 nights $624

Last booked 2 days ago
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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps7
  • Bedrooms4
  • PetsNo

    4.3★

    Good

  • Sykes rating

Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. Beach 10 min. WiFi. Roadside parking. Shop and pub 5 min. Poole 32.5 miles. (Ref. 994432)

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


for 7 nights $1184

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A brick townhouse with two bay windows a gray door and a black door at 15 Hardwick Street Weymouth
27
Weymouth, Dorset, DT4
  • Sleeps9
  • Bedrooms4
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A end-terrace house resting in Weymouth, Dorset. Close to beach. Enclosed garden. TVs in all bedrooms. Dorchester 7.4 miles; Bridport 19 miles. (Ref. 1049744)

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


for 7 nights $1234

Last booked 2 days ago
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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A living room with a blue sofa orange cushions a floral armchair green curtains a black fireplace and a wooden TV cabinet at Georgian Hideaway in Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.3★

    Good

  • Sykes rating

Georgian Hideaway, a quirky abode situated in the seaside town of Weymouth in Dorset. Near beach. Near shop. Near pub. Enclosed garden. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1154207)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights $802

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A front view of a brick house with a white door and blue garage door and a palm tree in the garden at Milton House in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.3★

    Good

  • Sykes rating

A homely, mid-terraced holiday property resting in Weymouth, Dorset. Off-road parking. Pet-free. Close to a beach and amenities. Dorchester 6.6 miles; Bridport 18.2 miles. (Ref. 1116564)

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


for 7 nights $828

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A sitting room with sofas chairs and a round coffee table at Marina Vista in Weymouth
21
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    3.7★

    Good

  • Sykes rating

Centrally located first floor apartment with views over the marina in Weymouth, close to shops and beach. Wifi, Off road private parking. (Ref. 994383)

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


for 7 nights $896

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
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 $921

Last booked yesterday
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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A patio with wooden chairs and a table outside a brick building with open double doors at Hide-A-Way in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. Dorchester 8.8 miles; Bridport 19.5 miles; Bournemouth 38.4 miles. (Ref. 1169910)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly


for 7 nights $582

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A street view of row houses with brick walls and bay windows with plants in front at Sandsfoot Rest in Weymouth
26
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

An attractive, Edwardian terraced house situated in Weymouth, Dorset. Woodburner. WiFi. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1001484)

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


for 7 nights $799

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-appointed, first-floor apartment resting in Weymouth, Dorset. Sea glimpses. Close to amenities, attractions and beach. Stylish. Off-road parking. Open-plan living. Near AONB. Dorchester 8.6 miles; Bridport 18.6 miles. (Ref. 1123245)

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


for 7 nights $736

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
A row of terraced houses with different colored facades on a paved street at Cove Street Cottage in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, three-storey home resting in Weymouth, Dorset. Close to amenities, harbour, and the beach. Family-friendly. Stylish. Elevated terrace. Central. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1122030)

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


for 7 nights $875

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
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 $887

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How we calculate the "Was" price

Our 'Was' price shows the average price for this property over the last 60 days, so you can see how today's price compares.
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