Winter Short Breaks in Dorset

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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
  • An exterior courtyard with stone buildings a staircase and no parking signs at George's House in Brewers Quay Harbour
    28
    Brewers Quay Harbour, Dorset
    • Sleeps7
    • Bedrooms4
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Four bedrooms in Kellaway Court, Weymouth. (Ref. 994219)

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

    3 nights from Mon 4th Jan From £800

    Last booked 1 hour ago
    Book now
  • A garden with a house and patio furniture at The Pebble in Dorchester
    23
    Melbury Osmond near Yetminster, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      5.0★

      Perfect

    • Dream Cottages rating

    The Pebble is a delightful holiday cottage in Melbury Osmond near Yetminster, offering an enclosed garden and private parking. (Ref. 1197188)

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

    3 nights from Sun 29th Nov From £405

    Last booked yesterday
    Book now
  • The driveway and entrance of a house with trees plants a small shed and a black cat at Nuthatch in Honiton
    12
    Honiton, Devon
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    A delightful, single-storey home resting in Stockland near Honiton, Devon. (Ref. 1131012)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Hot Tub

    3 nights from Sun 29th Nov From £492

    Last booked 2 days ago
    Book now
  • A white cottage with a thatched roof and potted plants outside on a roadside at Amy Cottage in West Lulworth
    43
    West Lulworth, Dorset
    • Sleeps6
    • Bedrooms4
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Amy Cottage is a beautiful thatched cottage with a toasty gas fire and accepting pets, located in Dorset's West Lulworth on the Jurassic coastline. (Ref. 1166887)

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

    3 nights from Sat 28th Nov From £731

    Book now
  • A small A-frame house with a wooden deck and stairs surrounded by trees and grass at Apple Tree Lodge in Gillingham
    23
    Gillingham, Dorset
    • Sleeps5
    • Bedrooms3
    • Pet FriendlyYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Unique, A-frame lodge placed near Gillingham in Dorset. (Ref. 970181)

    • Pets go free
    • Wi-fi
    • Off-road parking
    • Ground floor bedroom
    • Dishwasher

    3 nights from Mon 30th Nov From £417

    Book now
  • Exterior view of a brick cottage with green front door and multiple white windows at Millers Cottage in Puddletown
    32
    Puddletown, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Miller’s Cottage is a snug and romantic dwelling located in the village of Puddletown, nearby a river in Dorset, with a woodburning stove and welcoming one pet. (Ref. 1160443)

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

    3 nights from Sat 28th Nov From £368

    Last booked yesterday
    Book now
  • Stone cottages with gravel courtyard and greenery at Coombe Orchard in Swanage
    17
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • Pet FriendlyYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Perfect cottage for 2, close to Swanage, Open plan living area for two people, dog friendly. (Ref. 994113)

    • Pets go free
    • Off-road parking
    • Ground floor bedroom
    • Baby-friendly

    3 nights from Sun 29th Nov From £439

    Book now
  • A stone and brick cottage with a tiled roof and a small garden beside a road at Way's Forge in Piddlehinton
    24
    Piddlehinton, Dorset
    • Sleeps3
    • Bedrooms2
    • Pet FriendlyYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Located in countryside village of Piddlehinton, Way’s Forge is a lovely cosy holiday retreat. (Ref. 994768)

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

    3 nights from Sat 28th Nov From £508

    Book now
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.2★

      Good

    • Dream Cottages rating

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. (Ref. 1111030)

    • Wi-fi
    • Dishwasher

    3 nights from Sun 29th Nov From £642

    Book now
  • An exterior view of a building with a door and windows and flower pots at the entrance at Sandy Haven in Swanage
    37
    Swanage, Dorset
    • Sleeps4
    • Bedrooms2
    • Pet FriendlyNo

      4.7★

      Outstanding

    • Dream Cottages rating

    Sandy Haven is a delightful, ground-floor apartment resting in Swanage, Dorset. (Ref. 1140492)

    • Wi-fi
    • Ground floor bedroom

    3 nights from Sat 28th Nov From £554

    Book now
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