Dorset Holiday Cottages

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    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A street view of a cottage with brick and stone walls with bushes and flowers outside at Apple Tree Cottage in Shillingstone near Sturminster Newton
    26
    Shillingstone near Sturminster Newton, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Helpful Holidays rating

    A cosy brick-and-flint terraced cottage, within the pretty Dorset village of Shillingstone. (Ref. 925256)

    • Pets go free
    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from From $606

    Book now
  • A white door with the number 23 and flowering plants growing on a stone wall at Two Towers Cottage in Montacute
    30
    Montacute, Somerset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Helpful Holidays rating

    23 The Borough is a charming, Grade II listed home resting in a prime position in Montacute, Somerset. (Ref. 1142091)

    • Pets go free
    • Wi-fi
    • Dishwasher

    7 nights from From $731

    Book now
  • A house with a patio and garden at Brooklands in Uplyme
    23
    Uplyme, Devon
    • Sleeps10
    • Bedrooms4
    • Pet FriendlyNo

      4.8★

      Outstanding

    • Helpful Holidays rating

    This fantastic, four-bedroom holiday home rests in Uplyme, Devon. (Ref. 1131036)

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

    7 nights from From $1573

    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 $809

    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 $794

    Book now
  • A brick house with white windows and a tiled roof by a roadside at Oakapple Cottage in Swan Green near Lyndhurst
    Property has offers
    47
    Swan Green near Lyndhurst, Hampshire
    • Sleeps9
    • Bedrooms4
    • Pet FriendlyYes

      4.2★

      Good

    • Helpful Holidays rating

    A detached 18th century property resting in the historic village of Lyndhurst, Hampshire. (Ref. 1067240)

    • Pets go free
    • Wi-fi
    • Off-road parking

    • 20% off - Thu 6th Aug to 30th Sep 2026

    7 nights from From $1717

    Book now
  • An aerial view of a building with a gravel driveway a parked car a fenced garden area and pathways surrounded by trees at Casterbridge Upwey near Weymouth
    33
    Upwey near Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Helpful Holidays rating

    Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. (Ref. 932161)

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

    7 nights from From $903

    Book now
  • A house with solar panels on the roof and a gravel driveway with plants in the foreground at The Old School Cottage in Tincleton near Dorchester
    61
    Tincleton, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.2★

      Good

    • Helpful Holidays rating

    Well-presented barn conversion, close to the rural Dorset hamlet of Tincleton. (Ref. 20691)

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

    7 nights from From $493

    Last booked yesterday
    Book now
  • A garden with furniture and a parasol at Maple Cottage Buckland Newton near Dorchester
    46
    Buckland Newton near Dorchester, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyYes

      4.3★

      Good

    • Helpful Holidays rating

    A tastefully decorated, semi-detached cottage resting near the Dorset town of Sturminster Newton. (Ref. 988550)

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

    7 nights from From $629

    Book now
  • An outdoor hot tub and seating area with wicker furniture in a garden setting at Pound Cottage in Uplyme
    36
    Uplyme, Devon
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyNo

      4.1★

      Good

    • Helpful Holidays rating

    A wonderful detached holiday home in Uplyme, Devon. (Ref. 1102278)

    • Wi-fi
    • Hot Tub
    • Dishwasher
    • Washing machine

    7 nights from From $896

    Book now
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