Osmington Cottages

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A living room with black leather sofas a glass coffee table with flowers and a lamp by the window at Harbourside Haven Apartment 3 in Weymouth
    17
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    An immaculate second-floor apartment resting in the centre of Weymouth. (Ref. 1059264)

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

    7 nights from $932

    Book now
  • A stone cottage with a wooden door and white framed windows with a stone wall and gate in front at Blueberry Cottage in Sutton Poyntz
    Property has offers
    28
    Sutton Poyntz, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. (Ref. 994009)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 10% off - Fri 5th Jun to 4th Sep 2026

    7 nights from $633

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  • A stone and blue wooden building with external staircases and balconies under a clear sky at Santiago House in Weymouth
    45
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    This charming, four-bedroom holiday home rests in Weymouth, Dorset. (Ref. 1043677)

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

    7 nights from $1406

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  • A brick and white building facade with multiple windows on Trinity Road
    34
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    A Grade II listed, spacious maisonette apartment over the first and second floor in the Dorset town of Weymouth. (Ref. 1011525)

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

    7 nights from $1110

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  • A red brick building with multiple windows and a sign on Trinity Road at Monarch Brewers Quay Harbour
    36
    Brewers Quay Harbour, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A delightful, romantic bolthole in the third-floor in Weymouth, Dorset. (Ref. 1078324)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $752

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  • A street view showing old and new boathouse buildings and inner harbour with boats in the background at Old Boathouse Weymouth
    23
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Centrally located in Weymouth beautiful holiday home for family or friends. (Ref. 994461)

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

    7 nights from $864

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  • A window view of a harbor with sailboats and buildings in the background at The Ferryman in Weymouth
    16
    Weymouth, Dorset
    • Sleeps5
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    A character-filled cottage located in the popular seaside town of Weymouth, Dorset. (Ref. 1017295)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from $851

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  • 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 $696

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  • A stone house with a light blue door and white framed windows by a small river with ducks and overhanging trees at Duck Cottage in Sutton Poyntz
    44
    Sutton Poyntz, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Beautifully appointed cottage, resting in the quaint village of Sutton Poyntz in Dorset. (Ref. 1008404)

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

    7 nights from $813

    Book now
  • Exterior view of a white townhouse with blue doors and railings and stone columns at Hops House in Brewers Quay Harbour
    25
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. (Ref. 994277)

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

    7 nights from $1059

    Last booked 4 hours ago
    Book now
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