Winter Short Breaks in Dorset

REFINE SEARCH

Your search returned 471 cottages.

Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View
  • An exterior view of a multi-story residential building with balconies and large windows at Townbridge Apartment in Weymouth
    34
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      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 Mon 15th Dec €713

    Secure your holiday with a 30% deposit* Book now
  • A glass table with sunglasses fruit bowl champagne bottle and glasses overlooking a beach and sea at 123 On The Sea in Weymouth
    Property has offers
    33
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. (Ref. 1133961)

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

    3 nights from Fri 19th Dec was €574 €556

    Secure your holiday with a 30% deposit* Book now
  • A street view showing the entrance door of Little Gull Cottage with steps and potted plants in Weymouth
    21
    Weymouth, Dorset
    • 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 Wed 17th Dec €612

    Secure your holiday with a 30% deposit* Book now
  • A window seat with two mugs and a muffin on a tray overlooking a carousel and seaside at Shore View in Weymouth
    55
    Weymouth, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    26 Esplanade, a delightful coastal holiday home nestled in the town of Weymouth in Dorset. (Ref. 1118900)

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

    3 nights from Mon 15th Dec €1284

    Secure your holiday with a 30% deposit* Book now
  • A living room with a blue sofa and ottoman near a fireplace and television at Owls Rest in Weymouth
    35
    Weymouth, Dorset
    • 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 Sat 20th Dec €503

    Secure your holiday with a 30% deposit* Book now
  • A wooden deck with a picnic table set with glassware and fruit overlooking a grassy area and the sea at The Wave in Eype
    30
    Eype, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.5★

      Outstanding

    • Dream Cottages rating

    This wave shaped lodge is architect designed and has incredible panoramic sea views from the decking. (Ref. 994765)

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

    3 nights from Mon 15th Dec €1072

    Secure your holiday with a 30% deposit* Book now
  • A stone building with a thatched roof and multiple windows along a street at Farrier's Lodge in Corfe Castle
    27
    Corfe Castle, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    Stylish and contemporary cottage in the heart of Corfe Castle, Dorset. (Ref. 994182)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 15th Dec €635

    Secure your holiday with a 30% deposit* Book now
  • A garden with a shed and a bench overlooking a body of water at Harbour View Mudeford in Christchurch
    Property has offers
    26
    Christchurch, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    Luxury coastal ground floor property, located on Fishermans Bank, Mudeford. (Ref. 1006623)

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

    • €456 off - Tue 30th Dec 2025 to 7th Jan 2026

    3 nights from Sat 20th Dec was €917 €814

    Secure your holiday with a 30% deposit* Book now
  • A bungalow with a tiled roof and gravel front garden with plants at The Willows in Preston Weymouth
    Property has offers
    29
    Preston, Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.8★

      Outstanding

    • Dream Cottages rating

    This delightful, two-bedroom bungalow rests in Preston, Dorset. (Ref. 1126160)

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

    3 nights from Fri 19th Dec €683

    Secure your holiday with a 30% deposit* Book now
  • Exterior view of a brick building with balconies windows and surrounding garden at Ocean Watch 5 in Greenhill
    17
    Greenhill, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Modern, bright apartment with sea views over to Weymouth Bay. (Ref. 1098447)

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

    3 nights from Mon 15th Dec €765

    Secure your holiday with a 30% deposit* Book now
Most relevant
  • Most relevant
  • Price (lowest first)
  • Price (highest first)
  • Sleeps (lowest first)
  • Sleeps (highest first)
  • Rating (lowest first)
  • Rating (highest first)
  • Location (A to Z)
  • Location (Z to A)
  • Property name (A to Z)
  • Property name (Z to A)
10
  • 10
  • 20
  • 50
  • 100
Map View

Quick links

Popular Destinations