Summer Breaks in Dorset

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Your search returned 505 cottages.

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  • A row of brick terraced houses with bay windows and small front gardens at Covecastle Cottage in Weymouth
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. (Ref. 994072)

    • Wi-fi
    • Dishwasher
    • Washing machine

    7 nights from Mon 1st Jun €828

    Secure your holiday with a 30% deposit* Book now
  • A stone house with a small porch table and chairs next to a gravel driveway surrounded by bushes at Glyde House in Dorchester
    55
    Dorchester, Dorset
    • Sleeps8
    • Bedrooms5
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Glyde House is a detached property situated in Dorchester, Dorset. (Ref. 1150284)

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

    7 nights from Sat 6th Jun €1783

    Secure your holiday with a 30% deposit*
    Last booked today
    Book now
  • A house with large glass windows and a stone path leading to it surrounded by a garden at The Cart Barn in Ridge near Chilmark
    28
    Ridge near Chilmark, Wiltshire
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.9★

      Outstanding

    • Dream Cottages rating

    Fabulous conversion of a former cart shed set in peaceful surroundings and rolling countryside. (Ref. 988879)

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

    7 nights from Fri 28th Aug €1000

    Secure your holiday with a 30% deposit*
    Last booked 7 hours ago
    Book now
  • An old stone building with multiple gables and windows behind a stone wall at The Old Portland Courthouse in Portland
    33
    Portland, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    The Old Portland Courthouse is spacious, comfortable luxury holiday home. (Ref. 994487)

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

    7 nights from Sat 29th Aug €1692

    Secure your holiday with a 30% deposit* Book now
  • A building with balconies and stairs in front with a palm tree on the side at Lookout in Cove Castle
    38
    Cove Castle, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.8★

      Outstanding

    • Dream Cottages rating

    Comfortable Spanish style holiday home in Weymouth. (Ref. 994352)

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

    7 nights from Fri 28th Aug €1093

    Secure your holiday with a 30% deposit* Book now
  • A stone and brick cottage with a thatched roof surrounded by plants and flowers at Forge Cottage in West Lulworth
    30
    West Lulworth, Dorset
    • Sleeps5
    • Bedrooms3
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Short description: Ideal stay for walkers and ramblers to explore the Jurassic Coast. (Ref. 994203)

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

    7 nights from Fri 5th Jun €1304

    Secure your holiday with a 30% deposit* Book now
  • The exterior entrance of a red brick building with blue door and blue trim around windows at Seasides in Weymouth
    Property has offers
    55
    Weymouth, Dorset
    • Sleeps13
    • Bedrooms6
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Lovingly renovated Seasides offers, beach, sea and harbour views, suitable for large family gatherings close to shops and amenities. (Ref. 1056791)

    • Wi-fi
    • Off-road parking
    • Dishwasher
    • Washing machine
    • Baby-friendly
    • Games room
    • Sky TV

    • 20% off - Sun 2nd Nov to 9th Nov 2025

    • 20% off - Sun 9th Nov to 1st Dec 2025

    • 20% off - Mon 1st Dec to 21st Dec 2025

    7 nights from Fri 26th Jun €3854

    Secure your holiday with a 30% deposit* Book now
  • A single-story dark wooden house with multiple windows and a front door on a lawn at Rectory Farm View in Queen Camel near Yeovil
    47
    Queen Camel near Yeovil, Somerset
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Bright, spacious ground floor holiday home on the outskirts of Queen Camel, amongst beautiful Somerset countryside. (Ref. 957130)

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

    7 nights from Mon 1st Jun €1084

    Secure your holiday with a 30% deposit* Book now
  • Front view of a brick house with white framed windows a white door two black chairs and a palm tree at Reaver Brewers Quay harbour
    27
    Brewers Quay harbour, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.6★

      Outstanding

    • Dream Cottages rating

    Sleeping four near harbourside in Weymouth. (Ref. 994584)

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

    7 nights from Fri 19th Jun €1077

    Secure your holiday with a 30% deposit* Book now
  • A street view showing the old boathouse and new boathouse buildings with the inner harbour and boats in the background at New Boathouse in Weymouth
    18
    Weymouth, Dorset
    • Sleeps7
    • Bedrooms4
    • PetsNo

      4.3★

      Good

    • Dream Cottages rating

    Enjoyable holiday home close to the Old Harbour in Weymouth for large groups. (Ref. 994432)

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

    7 nights from Sat 29th Aug €1398

    Secure your holiday with a 30% deposit* Book now
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