Weymouth Holiday Cottages

Your search returned 21 cottages.

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    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A house with outdoor seating area at Budmouth Upwey near Weymouth
    42
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.4★

      Good

    • Helpful Holidays 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)

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

    7 nights from From £604

    Book now
  • A house with stone and wooden exterior at Everdene Upwey near Weymouth
    46
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Helpful Holidays rating

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

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

    7 nights from From £673

    Book now
  • A barn style house with gravel driveway and green field at Shepherd's Barn Between Milborne St Andrew and Winterborne Whitechurch
    Property has offers
    24
    Between Milborne St Andrew and Winterborne Whitechurch, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      5.0★

      Perfect

    • Helpful Holidays rating

    A superb, detached barn conversion set in the countryside near Winterborne Whitechurch. (Ref. 5188)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    • 5% off - Wed 1st Jul to 31st Aug 2026

    7 nights from From £646

    Book now
  • An exterior view of Shepherd Oak near Weymouth with plants and a wooden wall
    51
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.3★

      Good

    • Helpful Holidays rating

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

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

    7 nights from From £604

    Last booked yesterday
    Book now
  • The exterior wall of a yellow building with a white door and window and potted plants along the wall at Cuckoo Cottage in Bridport
    19
    Bridport, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyNo

      4.9★

      Outstanding

    • Helpful Holidays rating

    A romantic pied-a-terre in the bustling market town of Bridport. (Ref. 1004940)

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

    7 nights from From £400

    Last booked yesterday
    Book now
  • A wooden house with a gray slate roof and patio furniture in a garden at Bramshurst in Upwey near Weymouth
    32
    Upwey near Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. (Ref. 932159)

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

    7 nights from From £593

    Book now
  • A brick house with a sunroom and patio furniture in a garden at South Lodge in Hazelbury Bryan
    30
    Hazelbury Bryan, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      5.0★

      Perfect

    • Helpful Holidays rating

    A beautifully furnished annexe cottage on the edge of the little hamlet of Hazelbury Bryan in Dorset. (Ref. 969185)

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

    7 nights from From £432

    Book now
  • Exterior view of a building with black doors and windows a wooden picnic table and umbrella on a patio at Rowdens Barn in Winterborne Stickland
    Property has offers
    36
    Winterborne Stickland, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Beamed, single-storey holiday cottage near Winterborne Stickland. (Ref. 905898)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Electric car charging
    • Ground floor bedroom
    • Dishwasher
    • Washing machine
    • Baby-friendly

    • 5% off - Wed 1st Jul to 31st Aug 2026

    7 nights from From £457

    Last booked yesterday
    Book now
  • A stone pathway leads to a white house with a slate roof surrounded by trees and garden at Marles Farmhouse in Salwayash
    43
    Salwayash, Dorset
    • Sleeps12
    • Bedrooms6
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Helpful Holidays rating

    Beautiful converted farmhouse. (Ref. 976544)

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

    7 nights from From £1520

    Book now
  • A stone house with a green front door four windows a grass lawn and a paved pathway at West Bay Holiday Home in West Bay
    42
    West Bay, Dorset
    • Sleeps8
    • Bedrooms4
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Helpful Holidays rating

    A superb, detached property nestled on a quiet residential estate in West Bay. (Ref. 1075057)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine

    7 nights from From £907

    Last booked yesterday
    Book now
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Why book a cottage in Weymouth?

Weymouth is a bustling seaside town with a lovely,sandy beach nestled in a sheltered bay. The gentle, shallow waters make it a great destination for families with young children and there are also many family-friendly attractions close by, such as the sealife centre and sandworld sculpture park. Weymouth Harbour is often packed full of boats and just off the tip of the coast, reached by a causeway, is the Isle of Portland. It's great for outdoor adventurers as you can try rock climbing, abseiling and sailing. It is also a paradise for wildlife, with many rare birds choosing to stop here on their migratory path.

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