Weekend Breaks in Weymouth

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Your Weymouth, Dorset search returned 321 cottages

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  • 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
  • 10% off - Sun 12th Apr to 1st May 2026


for 3 nights £582

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Comfortable family seaside holiday home in Weymouth. Two dogs welcome. Rear garden. Wifi. Beach 10 min. Shop and pub 5 min. Isle of Portland 8 miles. (Ref. 994187)

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


for 3 nights £823

Last booked 3 hours ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

A lovely one-bedroom holiday home resting in Weymouth, Dorset. Romantic. Off-road parking. Private garden. Near a beach. Dorchester 10.2 miles; Bridport 18.8 miles. (Ref. 1092449)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine


for 3 nights £493

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. Close to amenities. Near beach. Enclosed courtyard. Dorchester 7.1 miles; Bridport 19.1 miles. (Ref. 1129331)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights £581

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • 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 3 nights £570

Last booked yesterday
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  • 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 3 nights £486

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    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 3 nights £642

  • 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 3 nights £608

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Tourist Board rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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


for 3 nights £520

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern, bright apartment with sea views over to Weymouth Bay. Short walk to the beach and a casual stroll to the town centre. Wifi and off-road parking. Great base for exploring Weymouth and the surrounding areas. (Ref. 1098447)

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


for 3 nights £688

  • 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 3 nights £652

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Tourist Board rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 3 nights £520

  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.5

    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 3 nights £1157

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A superb barn conversion resting in Puncknowle near Burton Bradstock, Dorset. WiFi. Balcony. Rural location. Bridport 6.5 miles; Weymouth 12.9 miles; Swanage 38.7 miles. (Ref. 1098014)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 3 nights £558

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Link detached modern annex lodge in the Dorset Coastal village of Osmington. Wifi. Parking for two cars. Short drive to Weymouth. (Ref. 994794)

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


for 3 nights £502

  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Directly on the seafront. First floor period apartment. Bright and comfortable. Breath-taking sea views. En-suite shower room. WiFi. Off road parking with garage. (Ref. 993989)

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


for 3 nights £695

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2

    Good

  • Sykes rating

Perfectly located on the harbour side in the heart of Weymouth. Watch the boats sail by and the daily catch being landed. (Ref. 994172)

  • Wi-fi
  • Washing machine


for 3 nights £438

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

The Loft @ No36, a contemporary, third-floor apartment situated in the heart of Weymouth in Dorset, enjoying sea views with the beach on your doorstep. Dorchester 7.8 miles; Bridport 19.1 miles. (Ref. 1162205)

  • Wi-fi
  • Off-road parking


for 3 nights £456

  • 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
  • 5% off - Sat 18th Apr to 22nd May 2026


for 3 nights £432

Last booked yesterday
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