Summer Breaks in Dorset

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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 street view showing old and new boathouse buildings and inner harbour with boats in the background at Old Boathouse Weymouth
    Property has offers
    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 Sat 29th Aug $1266

    Last booked yesterday
    Book now
  • A garden with seating area and conservatory at Honeypot Cottage in Weymouth
    Property has offers
    24
    Preston, Dorset
    • Sleeps4
    • Bedrooms3
    • PetsNo

    • Dream Cottages rating

    A traditional, thatched cottage resting within the village of Preston. (Ref. 1201976)

    • Wi-fi
    • Washing machine

    7 nights from Sat 6th Jun $808

    Last booked 2 days ago
    Book now
  • A brick residential building with multiple windows a gated entrance and a small staircase at Ocean Watch 1 in Greenhill
    Property has offers
    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 Sat 18th Jul $1494

    Last booked yesterday
    Book now
  • A house with a red tiled roof garage a tree with white flowers and green lawn at Bridge Studio in Broad Chalke
    Property has offers
    39
    Near Broad Chalke, Wiltshire
    • Sleeps3
    • Bedrooms1
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Superb barn conversion in idyllic village, Stylishly furnished and with great space. (Ref. 988924)

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

    7 nights from Fri 28th Aug $818

    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 Fri 5th Jun $893

    Book now
  • A living room with a sea view at Portland View in Portland Bill
    Property has offers
    21
    Portland Bill, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

    • Dream Cottages rating

    A beautifully presented apartment with stunning views across the bay and Portland Bill. (Ref. 1201975)

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

    7 nights from Sat 29th Aug $1152

    Book now
  • A row of brick terraced houses with white doors and windows along a street at Castle Cove View in Castle Cove
    Property has offers
    29
    Castle Cove, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Wonderfully positioned townhouse just moments from Sandsfoot beach and the South West Coast path. (Ref. 1059103)

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

    7 nights from Fri 7th Aug $2685

    Book now
  • An outdoor patio with a round wooden table and six chairs next to a garden and stone wall overlooking the sea at Beach View Apartment 2 in Greenhill
    Property has offers
    35
    Greenhill, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    Excellent period apartment in Weymouth close to the esplanade. (Ref. 993988)

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

    7 nights from Sat 25th Jul $3504

    Book now
  • A long brick and flint building with multiple doors and windows a grass lawn and flowers at The Old Stables in Winterborne Stickland
    39
    Winterborne Stickland, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Single-storey pet-friendly barn conversion in an attractive lawned courtyard. (Ref. 18978)

    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    7 nights from Tue 18th Aug $1927

    Last booked 2 days ago
    Book now
  • A two-story brick house behind a stone and brick wall with a black gate and a tree nearby at The Nook in Weymouth
    38
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    The Nook is a charming, pet-friendly cottage resting near the beach in the town of Weymouth in Dorset, boasting a woodburning stove and enclosed garden. (Ref. 1107935)

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

    7 nights from Sat 1st Aug $1868

    Book now
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