Luxury Holiday Cottages Dorset

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Your search returned 42 cottages.

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  • 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
    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 €1216

    Secure your holiday with a 30% deposit* Book now
  • A backyard with a glass conservatory attached to a stone and tile roof building and wooden outdoor furniture on a patio at Fossil Barn in Weymouth
    18
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Contemporary barn conversion, close to the Dorset coast. (Ref. 994207)

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

    7 nights from €755

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    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 €710

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. (Ref. 932160)

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

    7 nights from €745

    Secure your holiday with a 30% deposit*
    Last booked 8 hours ago
    Book now
  • A stone cottage with a tiled roof and potted plants outside at Leys At Valley View Farm in Uplyme
    44
    Uplyme, Devon
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    Leys at Valley View Farm is a high specification luxury barn conversion. (Ref. 994328)

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

    7 nights from €1557

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of a house with a glass balcony and patio surrounded by trees and bushes at 6 Red Sails in Sandbanks
    47
    Sandbanks, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    6 Red Sails is a magnificent townhouse in Sandbanks, Dorset, with open-plan living, a balcony with garden views and is close to the beach. (Ref. 1175111)

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

    7 nights from €1087

    Secure your holiday with a 30% deposit* Book now
  • A garden with a deck, table, and chairs overlooking the sea at Hoppapill House in Bournemouth
    48
    Bournemouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    A fantastic ground-floor apartment located in West Cliff near Bournemouth, Dorset. (Ref. 1083610)

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

    7 nights from €1780

    Secure your holiday with a 30% deposit* Book now
  • A large stone manor house with bay windows and ivy on the walls with a garden and small pond in front at Milton Manor in Milton On Stour
    Property has offers
    82
    Milton On Stour, Dorset
    • Sleeps33
    • Bedrooms14
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    This stunning historic manor nestles in the heart of Milton on Stour, Dorset. (Ref. 1026929)

    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room

    • 5% off - Fri 7th Mar 2025 to 30th Apr 2026

    7 nights from €6407

    Secure your holiday with a 30% deposit* Book now
  • An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
    51
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.3★

      Good

    • Dream Cottages rating

    Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. (Ref. 932158)

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

    7 nights from €710

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of three adjacent terraced houses with bay windows and chimneys at Harbourside House in Brewers Quay Harbour
    50
    Brewers Quay Harbour, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Beautiful holiday cottage over three floors beside Old Harbour in Weymouth. (Ref. 994256)

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

    7 nights from €1557

    Secure your holiday with a 30% deposit* Book now
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