May Half-Term Breaks

Your search returned 157 cottages.

REFINE SEARCH
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

    How reviews work

    A property's star rating is the average of the star ratings received from guests that wish for their review to be published
  • A brick house with a round balcony and glass doors at 4 Holt Court in Salisbury
    25
    Salisbury, Wiltshire
    • Sleeps6
    • Bedrooms3
    • PetsNo

      4.9★

      Outstanding

    • Dream Cottages rating

    Outstanding loft-style apartment in the heart of Salisbury. (Ref. 988938)

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

    3 nights from Sat 23rd May £1064

    Book now
  • A row of attached houses with different exterior finishes on a street at Home From Home in Fortuneswell
    57
    Fortuneswell, Dorset
    • Sleeps8
    • Bedrooms4
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    Home From Home is a delightful cottage nestled in the village of Fortuneswell in Dorset, Isle of Portland and is pet-friendly and near the beach. (Ref. 1158103)

    • Wi-fi
    • Washing machine

    3 nights from Thu 28th May £468

    Last booked 2 days ago
    Book now
  • A brick house with white framed windows a white garage door and a paved driveway at Portside Greenhill Weymouth
    24
    Greenhill Weymouth, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.4★

      Good

    • Dream Cottages rating

    This plush, two-storey property is located in the Greenhill suburb of Weymouth, Dorset. (Ref. 1093991)

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

    3 nights from Fri 29th May £559

    Book now
  • A brick house facade with a black door and five windows at Pixie Cottage in Weymouth
    26
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

    A delightful Weymouth terraced cottage, sleeps 4, close to the harbour and walking distance to the beach. (Ref. 1132245)

    • Wi-fi
    • Washing machine

    3 nights from Sun 24th May £535

    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

      4.6★

      Outstanding

    • Dream Cottages rating

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

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

    3 nights from Mon 25th May £1209

    Last booked yesterday
    Book now
  • An outdoor patio with a round metal table and four chairs near a wooden fence and a small brick building at Pops Barn in Downton
    12
    Downton, Wiltshire
    • Sleeps2
    • Bedrooms1
    • PetsYes

      4.2★

      Good

    • Dream Cottages rating

    A perfect hideaway tucked behind the main street in the bustling village of Downton. (Ref. 988934)

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

    3 nights from Tue 26th May £372

    Last booked yesterday
    Book now
  • 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
    • PetsYes

      4.5★

      Outstanding

    • Dream Cottages rating

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

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Mon 25th May £420

    Last booked yesterday
    Book now
  • A living room with a grey sofa pillows an armchair a fireplace with a fire a wall mounted TV a bookshelf and stairs leading to another floor at Old Ropemakers Cottage in Bridport
    Property has offers
    37
    Bridport, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsYes

      3.9★

      Good

    • Dream Cottages rating

    Old Ropemakers Cottage is a characterful cottage with woodburning stove situated near the beach in the town of Bridport, Dorset and a pet friendly policy. (Ref. 1155307)

    • Wi-fi
    • Washing machine

    • 10% off - Sat 30th May to 31st Jul 2026

    3 nights from Sun 24th May was £492 £457

    Last booked 2 days ago
    Book now
  • A brick house with white framed windows and door with two black chairs and a small table outside at Nuke in Weymouth
    Property has offers
    22
    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo

      4.6★

      Outstanding

    • Dream Cottages rating

    This cottage boast style, character, and a fabulously contemporary interior. (Ref. 1005313)

    • Wi-fi
    • Dishwasher
    • Washing machine

    3 nights from Fri 22nd May £1046

    Book now
  • A stone walkway with plants along the side of a stone house at The Apple Loft at Jordan House in Preston
    21
    Preston, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsNo

      4.2★

      Good

    • Dream Cottages rating

    The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. (Ref. 1149531)

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

    3 nights from Fri 22nd May £507

    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