Short Breaks in Weymouth

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Your search returned 292 cottages.

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  • The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
    15
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    7 nights from $825

    Secure your holiday with a 30% deposit*
    Last booked 9 hours ago
    Book now
  • A row of attached houses with one blue house covered in climbing plants and flowers in front at Fenders Brewers Quay Harbour
    30
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    7 nights from $825

    Secure your holiday with a 30% deposit* Book now
  • 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
    Property has offers
    38
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages 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. (Ref. 1140944)

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

    • 5% off - Fri 3rd Apr to 2nd May 2026

    7 nights from $922

    Secure your holiday with a 30% deposit* Book now
  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. (Ref. 932157)

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

    7 nights from $840

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • 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
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    This is a beautiful ground-floor apartment within a townhouse on the Weymouth seafront in Dorset. (Ref. 1034440)

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

    7 nights from $794

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey
    18
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    This picturesque cottage, situated in the village of Upwey, with parking. (Ref. 994658)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    7 nights from $669

    Secure your holiday with a 30% deposit* Book now
  • A brick house with a brown door and windows a driveway wooden benches and a garage at Chickerell House Weymouth
    32
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. (Ref. 1152691)

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

    7 nights from $973

    Secure your holiday with a 30% deposit*
    Last booked 4 hours ago
    Book now
  • A balcony with a small wooden table and chairs overlooking a waterway and buildings at Harbour Hideaway in Weymouth
    16
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A second-floor apartment resting in Weymouth. (Ref. 1007302)

    • Wi-fi
    • Off-road parking
    • Dishwasher

    7 nights from $700

    Secure your holiday with a 30% deposit* Book now
  • A balcony with wicker chairs a table and glass panels overlooking a harbor at Bears Apartment in Castletown Portland
    27
    Castletown, Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A well-positioned, fourth-floor apartment resting in Castletown, Dorset. (Ref. 1119638)

    • Wi-fi
    • Swimming pool
    • Dishwasher
    • Washing machine

    7 nights from $760

    Secure your holiday with a 30% deposit* Book now
  • A living room with a TV on a white stand and a black sofa with animal print cushions at Sunny Days in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Modern refurbished terraced cottage in Weymouth, sleeping 4, short walk to the beach and town, WiFi, Off road parking for 1 car. (Ref. 994696)

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

    7 nights from $738

    Secure your holiday with a 30% deposit* Book now
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