Holiday Cottages for October Half term

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Your search returned 464 cottages.

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  • A row of terraced houses with flowers and bushes in front and a view of the sea at Langham Cottage in Portland
    35
    Portland, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Situated in the Isle of Portland, Langham Cottage is very comfortable and spacious holiday home. (Ref. 994321)

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

    3 nights from Sun 26th Oct $536

    Secure your holiday with a 30% deposit* Book now
  • A paved driveway with flower pots alongside a single story house with green doors and stone accents at Bumble Bee Retreat in Tytherleigh
    26
    Tytherleigh, Devon
    • Sleeps4
    • Bedrooms1
    • PetsYes

      5.0★

      Perfect

    • Dream Cottages rating

    This charming, single-storey cottage rests in the beautiful countryside of Tytherleigh, Devon. (Ref. 1134052)

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

    3 nights from Mon 27th Oct $817

    Secure your holiday with a 30% deposit* Book now
  • The front exterior of a brick house with several windows a wooden door and a white garage door at Mariners Rest in Weymouth
    15
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Set in a lovely and quiet residential area of Weymouth, the house is a comfortable getaway for a family. (Ref. 994377)

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

    3 nights from Sun 26th Oct $752

    Secure your holiday with a 30% deposit* Book now
  • A two story house with chimneys surrounded by a garden with grass bushes and small trees at West Ridge in Boscombe
    62
    Boscombe, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.7★

      Outstanding

    • Dream Cottages rating

    A substantial, detached property built in the 1900s, situated in the Boscombe region near Bournemouth. (Ref. 923145)

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

    3 nights from Tue 28th Oct $952

    Secure your holiday with a 30% deposit* Book now
  • A row of attached houses with brick and beige facades on a street with sidewalks at Globe Cottage in Weymouth
    27
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms3
    • PetsNo

      4.4★

      Good

    • Dream Cottages rating

    Three bedroom terraced property in central Weymouth. (Ref. 1095056)

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

    3 nights from Fri 24th Oct $961

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

      4.5★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Fri 31st Oct $1058

    Secure your holiday with a 30% deposit* Book now
  • Stone cottages with gravel courtyard and greenery at Coombe Orchard in Swanage
    17
    Swanage, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

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

    • Off-road parking
    • Ground floor bedroom
    • Baby-friendly

    3 nights from Sun 26th Oct $553

    Secure your holiday with a 30% deposit* Book now
  • A harbor with boats docked near buildings and a raised drawbridge at Harbours Edge in Brewers Quay Harbour
    27
    Brewers Quay Harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.1★

      Good

    • Dream Cottages rating

    Perfectly located on the harbour side in the heart of Weymouth. (Ref. 994172)

    • Wi-fi
    • Washing machine

    3 nights from Sun 2nd Nov $578

    Secure your holiday with a 30% deposit* Book now
  • A stone house with green garage doors and white windows next to a building with a boarded-up window at Swanage Driftwood in Swanage
    37
    Swanage, Dorset
    • Sleeps10
    • Bedrooms5
    • PetsYes

      4.7★

      Outstanding

    • Dream Cottages rating

    Sleeps 10, large open plan living kitchen dining room. (Ref. 994706)

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

    3 nights from Sun 26th Oct $1224

    Secure your holiday with a 30% deposit* Book now
  • A street corner with rows of attached houses and a blue building in the background at Shrimp Cottage in Brewers Quay Harbour
    Property has offers
    49
    Brewers Quay Harbour, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes

    • Dream Cottages rating

    Shrimp Cottage is a tasteful house in Brewers Quay Harbour, Dorset, this pet-friendly abode boasts Smart TVs and is near the beach and other amenities. (Ref. 1173548)

    • Wi-fi
    • Dishwasher
    • Washing machine

    • 15% off - Fri 25th Jul to 22nd Aug 2025

    3 nights from Fri 31st Oct $852

    Secure your holiday with a 30% deposit* Book now
Most relevant
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