May Half-Term Breaks

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Your search returned 389 cottages.

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    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.4

      Good

    • 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

    3 nights from Tue 26th May €580

    Secure your holiday with a 30% deposit* Book now
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.9

      Outstanding

    • Dream Cottages rating

    Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. (Ref. 1144645)

    • Wi-fi
    • Baby-friendly

    3 nights from Mon 25th May €641

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    A homely, mid-terrace cottage based in Weymouth. (Ref. 1094925)

    • Wi-fi
    • Off-road parking
    • Baby-friendly

    3 nights from Sun 31st May €519

    Secure your holiday with a 30% deposit*
    Last booked yesterday
    Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.7

      Outstanding

    • Dream Cottages rating

    Old Harbour Townhouse, a delightful, three-storey abode set in the seaside town of Weymouth in Dorset. (Ref. 1159836)

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

    3 nights from Wed 27th May €879

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.4

      Good

    • Dream Cottages rating

    Lovely and comfortable cottage next to the harbour in Weymouth. (Ref. 994351)

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

    3 nights from Sun 31st May €572

    Secure your holiday with a 30% deposit* Book now
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Cosy property located in the coastal village of West Bexington. (Ref. 994761)

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

    3 nights from Sat 30th May €506

    Secure your holiday with a 30% deposit* Book now
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.4

      Good

    • Dream Cottages rating

    Beautiful and spacious cottage over three floors in Weymouth. (Ref. 994354)

    • Wi-fi
    • Washing machine
    • Baby-friendly

    3 nights from Sun 31st May €585

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    • Sleeps6
    • Bedrooms3
    • PetsNo

      5.0

      Perfect

    • Dream Cottages rating

    Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. (Ref. 1140944)

    • Wi-fi
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • 5% off - Fri 3rd Apr to 2nd May 2026

    3 nights from Sun 31st May €659

    Secure your holiday with a 30% deposit* Book now
    • Sleeps6
    • Bedrooms3
    • PetsYes

      4.6

      Outstanding

    • Dream Cottages rating

    This cosy lodge on a peaceful15 acre site, is resting near village of Milton on Stour in Dorset. (Ref. 967741)

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

    3 nights from Tue 26th May €519

    Secure your holiday with a 30% deposit* Book now
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5

      Outstanding

    • Dream Cottages rating

    Delightful terraced cottage. (Ref. 998253)

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

    3 nights from Sun 31st May €688

    Secure your holiday with a 30% deposit* Book now
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