Short Breaks in Weymouth

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Your search returned 284 cottages.

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  • A blue two-story building with bay windows and white doors on a brick street at Tradewinds Brewers Quay Harbour
    17
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Situated in front of the Old Harbour in Weymouth, Tradewinds is perfect base for couples. (Ref. 994737)

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

    7 nights from $979

    Secure your holiday with a 30% deposit* Book now
  • A row of brick terraced houses with bay windows and small front gardens at Covecastle Cottage in Weymouth
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. (Ref. 994072)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $687

    Secure your holiday with a 30% deposit* Book now
  • Front view of two adjoining houses with black doors and white brick walls with a paved driveway at Maisy Cottage in Weymouth
    25
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern and beautiful cottage in the heart of Weymouth. (Ref. 994369)

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

    7 nights from $762

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
  • A backyard view of a brick two-story house with patio furniture and a pond in front at Agua de Plata 16 Wakeling Island Silverlake in Dorchester
    43
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    16 Wakeling Island is a stylish, detached home resting in Crossways, Dorset. (Ref. 1138508)

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

    7 nights from $996

    Secure your holiday with a 30% deposit* Book now
  • A narrow street with houses on the right and a brick wall with plants on the left at Firkin Cottage Brewers Quay Harbour
    22
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Comfortable renovated cottage with rear garden and close to the town centre. (Ref. 994191)

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

    7 nights from $807

    Secure your holiday with a 30% deposit* Book now
  • A living room with sofas and cushions near glass doors with curtains and a rug at Admirals Retreat in Weymouth
    25
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Perfect couples retreat with WIFI. (Ref. 993912)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $682

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a brick house with white doors and windows outdoor chairs and plants at Footprint Brewers Quay Harbour
    Property has offers
    22
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. (Ref. 994201)

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

    • $467 off - Mon 29th Dec 2025 to 5th Jan 2026

    7 nights from $924

    Secure your holiday with a 30% deposit* Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    20
    Greenhill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Modern one level apartment. (Ref. 994505)

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

    7 nights from $779

    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 $816

    Secure your holiday with a 30% deposit* Book now
  • The front exterior of a brick house with a black door and white framed windows surrounded by green bushes at Admirals Quarter Apartment 4 in Weymouth
    30
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Modern ground floor Apartment. (Ref. 993910)

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

    7 nights from $643

    Secure your holiday with a 30% deposit* Book now
Most relevant
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