Self-Catering Weymouth Cottages

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Your search returned 289 cottages.

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  • A garden with flowers a wooden arch and a raised deck attached to a brick house at Little Retreat in Upwey
    21
    Upwey, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      5.0★

      Perfect

    • Dream Cottages rating

    Village pubs and tea rooms. (Ref. 994358)

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

    7 nights from £486

    Secure your holiday with a 30% deposit* Book now
  • An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
    33
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    The Old Portland Courthouse is spacious, comfortable luxury holiday home. (Ref. 994487)

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

    7 nights from £1176

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a stone and brick house with multiple windows and blue doors a patio with chairs a table and an umbrella and plants at The Gables in Brewers Quay Harbour
    18
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms4
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    Lovely 4 bedroom house in gated area. (Ref. 994213)

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

    7 nights from £815

    Secure your holiday with a 30% deposit* Book now
  • A blue building with bay windows and two white doors behind a black metal fence at Brewers Quay Harbour
    Property has offers
    23
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    All second floor. (Ref. 994293)

    • Wi-fi

    • 10% off - Fri 6th Jun to 2nd Aug 2025

    7 nights from £641

    Secure your holiday with a 30% deposit* Book now
  • A front view of a three-story end terrace house with a lawn and driveway at The Ferns in Weymouth
    25
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Comfortable family seaside holiday home in Weymouth. (Ref. 994187)

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

    7 nights from £787

    Secure your holiday with a 30% deposit* Book now
  • A street with parked cars stone wall and houses overlooking the sea at Bowleaze View in Weymouth
    Property has offers
    30
    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)

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

    • 10% off - Sat 12th Jul to 26th Jul 2025

    7 nights from £842

    Secure your holiday with a 30% deposit* Book now
  • A balcony with a round table holding a bottle and two wine glasses with two chairs and a sea view at Sunbeach in Weymouth
    24
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    A neat, first-floor apartment set overlooking the Pavillion on Weymouth seafront. (Ref. 1123724)

    • Wi-fi

    7 nights from £557

    Secure your holiday with a 30% deposit* Book now
  • A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
    Property has offers
    18
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. (Ref. 994432)

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

    • 5% off - Sat 6th Sep to 30th Sep 2025

    7 nights from £842

    Secure your holiday with a 30% deposit*
    Last booked 2 days ago
    Book now
  • A balcony with a table and two chairs overlooking a harbor with boats and buildings at Harbourside Penthouse in Brewers Quay Harbour
    21
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    A contemporary and spacious third floor apartment on the Old Harbourside in Weymouth. (Ref. 999829)

    • Wi-fi
    • Off-road parking

    7 nights from £654

    Secure your holiday with a 30% deposit* Book now
  • A rocky shoreline with a small beach a stone wall and garden plants at Weymouth Bay Apartment A in Weymouth
    49
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. (Ref. 1083146)

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

    7 nights from £649

    Secure your holiday with a 30% deposit* Book now
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