Upwey Cottages

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  • Boats docked in a harbor in front of buildings including Old Coastguard Apartment 2 in Weymouth
    Property has offers
    30
    Weymouth, Dorset
    • Sleeps8
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    On Weymouth Harbourside this is an extraordinarily spacious apartment, sleeps 8, tastefully renovated, Large en-suite showers to all rooms, harbour views, WiFi. (Ref. 994463)

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

    • 16% off - Thu 30th Oct 2025 to 5th Jan 2026

    7 nights from $1294

    Secure your holiday with a 30% deposit* Book now
  • A two-story brick house with a white entrance porch and cobblestone driveway at The Chocolate Box in Weymouth
    37
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely three-storey house resting in Weymouth, Dorset. (Ref. 1092302)

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

    7 nights from $1048

    Secure your holiday with a 30% deposit* Book now
  • A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth
    18
    Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon

    Beautiful seafront apartment within the popular resort of Weymouth in Dorset. (Ref. 1003083)

    • Wi-fi
    • Dishwasher

    7 nights from $653

    Secure your holiday with a 30% deposit* Book now
  • The exterior of a house with white walls and wooden paneling a patio area with a table umbrella and chairs at Whitegates Lodge in Osmington
    15
    Osmington, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Link detached modern annex lodge in the Dorset Coastal village of Osmington. (Ref. 994794)

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

    7 nights from $687

    Secure your holiday with a 30% deposit* Book now
  • An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey
    21
    Upwey, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A pretty village lodge, close to the seaside town of Weymouth in Dorset. (Ref. 1017591)

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

    7 nights from $598

    Secure your holiday with a 30% deposit* Book now
  • 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 $835

    Secure your holiday with a 30% deposit* Book now
  • A two-story corner house with a pink brick exterior and a bay window at Mermaid House in Brewers Quay Harbour
    41
    Brewers Quay Harbour, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This stylish and neat holiday home rests in Brewers Quay Harbour in Weymouth, Dorset. (Ref. 1093760)

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

    7 nights from $880

    Secure your holiday with a 30% deposit* Book now
  • A brick exterior of a cottage with white doors and windows at Rupert Cottage Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping 4 cosy cottage in Weymouth. (Ref. 994605)

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

    7 nights from $801

    Secure your holiday with a 30% deposit* Book now
  • A living room with leather sofas glass coffee table and a television near large windows overlooking boats at Harbourside Haven Apartment 4 in Weymouth
    20
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A stylish and contemporary apartment overlooking Weymouth Harbour in Dorset. (Ref. 1059265)

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

    7 nights from $835

    Secure your holiday with a 30% deposit* Book now
  • A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
    22
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Village pubs and tea rooms. (Ref. 994358)

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

    7 nights from $647

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
Most relevant
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