Weekend Breaks in Weymouth

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Your Weymouth, Dorset search returned 303 cottages

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A brick house exterior with two white garage doors two upper windows and two front doors with canopies at Sea Pebbles in Weymouth
34
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsNo

    3.8★

    Good

  • Sykes rating

Close to the harbour in Weymouth, Semi detached house, access to South West Coast path, WIFI, Close to shops, restaurants and café’s, suitable for families. (Ref. 994639)

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


for 3 nights £714

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A house with windows and a garden at Tithe Barn Cottage in Litton Cheney near Burton Bradstock
40
Litton Cheney near Burton Bradstock, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

Tithe Barn Cottage is a beautifully presented, dog-friendly 2-bedroom detached cottage at Litton Cheney, a village in the heart of the Dorset countryside. Bridport 6.5 miles; Dorchester 13.1 miles; Weymouth 16.4 miles; Yeovil 21.4 miles (Ref. 1174942)

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


for 3 nights £552

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A living room with a blue sofa orange cushions a floral armchair green curtains a black fireplace and a wooden TV cabinet at Georgian Hideaway in Weymouth
32
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsYes

  • Sykes rating

Georgian Hideaway, a quirky abode situated in the seaside town of Weymouth in Dorset. Near beach. Near shop. Near pub. Enclosed garden. Pet-friendly. Dorchester 7 miles; Bridport 17 miles. (Ref. 1154207)

  • Wi-fi
  • Dishwasher
  • Washing machine

  • 5% off - Fri 21st Feb to 31st Dec 2025


for 3 nights £533

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Front of a thatched cottage with green door flowers and stone wall at Cajun Cottage in West Lulworth
44
West Lulworth, Dorset, Bh20
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.4★

    Good

  • Sykes rating

A pretty thatched cottage located just a short walk from the beach at Lulworth Cove in Dorset. Sea-views. Woodburning stove. Parking. Wi-Fi. Dorchester 13 miles. (Ref. 1095869)

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

  • £769 off - Fri 19th Dec to 26th Dec 2025


for 3 nights £780

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An outdoor view of a cottage with a thatched roof and stone wall at Bracken Cottage in
11
Osmington, Dorset, DT3
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Bracken Cottage is a romantic property resting in the village of Osmington, Dorset, boasting an open-plan living area, is close to the beach and amenities. Weymouth 5.4 miles. (Ref. 1173628)

  • Wi-fi
  • Off-road parking


for 3 nights £450

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A brick cottage with a paved driveway a wooden door and a small lawn at Frome Lodge House in Frome Whitfield
22
Frome Whitfield, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.1★

    Good

  • Sykes rating

A charming, two-bedroom holiday home resting in Frome Whitfield, Dorset. Close to amenities. Pet-friendly. Families. Dorchester 2.5 miles; Yeovil 22.4 miles; Bournemouth 29.7 miles (Ref. 1132783)

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


for 3 nights £464

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A living room with sofas and a pool table next to large windows with red curtains at Waterson in Osmington
30
Osmington, Dorset, DT3
  • Sleeps7
  • Bedrooms3
  • PetsYes

    4.2★

    Good

  • Sykes rating

Semi-detached lovely holiday home perfect for families. Situated in Osmington Mills village. Garden. Welcomes two dogs. Shop 3 miles. Pub 2 miles. Beach 5 min. Weymouth 6 miles. (Ref. 994764)

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


for 3 nights £881

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Sunny Croft - 977681 - photo 1
28
Broadmayne near Dorchester, Dorset, DT2
  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

Sunny Croft is a delightful 1930s bungalow in Broadmayne, near Dorchester, Dorset. Stunning countryside views. Hot tub. Large garden. Private parking. Dorchester 4 miles; Weymouth 7.5 miles. (Ref. 977681)

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


for 3 nights £652

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A red brick residential building with multiple windows and a paved driveway near a tree at Flat 6 Thornlow Heights in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

A well-appointed, first-floor apartment resting in Weymouth, Dorset. Sea glimpses. Close to amenities, attractions and beach. Stylish. Off-road parking. Open-plan living. Near AONB. Dorchester 8.6 miles; Bridport 18.6 miles. (Ref. 1123245)

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

  • 5% off - Mon 22nd Dec 2025 to 5th Jan 2026


for 3 nights £449

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A balcony overlooking a city street at a property
27
Dorchester, Dorset, DT1
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Tourist Board rating

30 Princes House is a stylish apartment in Dorchester, Dorset, with superfast WiFi and off-road parking. Weymouth 8.3 miles. (Ref. 1190849)

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


for 3 nights £393

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A living room with a sofa, coffee table, and dining area at Beachcomb in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Beachcomb is a fine third-floor apartment located close to a beach in the town of Weymouth in Dorset, well-positioned to nearby attractions and amenities. Dorchester 7.7 miles; Bridport 21.2 miles; Poole 31.2 miles. (Ref. 1083686)

  • Wi-fi
  • Washing machine


for 3 nights £449

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A patio with wooden chairs and a table outside a brick building with open double doors at Hide-A-Way in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps2
  • Bedrooms1
  • PetsNo

  • Sykes rating

Hideaway is a fine, single-storey annex situated in Weymouth, Dorset, with open-plan living, Smart TV, and well-positioned to nearby beaches and amenities. Dorchester 8.8 miles; Bridport 19.5 miles; Bournemouth 38.4 miles. (Ref. 1169910)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly


for 3 nights £338

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A row of brick houses with blue and turquoise front doors and white windows on a street at Chapelhay Cottage in Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms3
  • PetsYes

    3.3★

  • Sykes rating

Chapelhay Cottage is a lovely, terraced cottage nestled into the seaside town of Weymouth, Dorset. Close shop and a pub. Close to a beach. Jurassic Coast. Portland 5.9 miles; Dorchester 8.4 miles; Lyme Regis 28.3 miles. (Ref. 1131030)

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


for 3 nights £614

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A row of terraced houses with different colored facades on a paved street at Cove Street Cottage in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A well-positioned, three-storey home resting in Weymouth, Dorset. Close to amenities, harbour, and the beach. Family-friendly. Stylish. Elevated terrace. Central. Dorchester 8.4 miles; Bridport 18.5 miles. (Ref. 1122030)

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


for 3 nights £627

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A house with ivy on one side a paved driveway and a porch with wooden furniture at Deer Leap House in Moreton
82
Moreton, Dorset, DT2
  • Sleeps15
  • Bedrooms7
  • PetsYes

    4.2★

    Good

  • Sykes rating

A spacious holiday home resting in Moreton, Dorset. Woodburning stove. Ground-floor living. Shared outdoor pool and tennis court. Terrace with furniture. Dorchester 6 miles; Weymouth 10.5 miles; Blandford Forum 14.9 miles. (Ref. 1060785)

  • Wi-fi
  • Off-road parking
  • Swimming pool
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 3 nights £1494

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A sitting area with two chairs a footstool and plantation shutters by a bay window overlooking a waterfront at Low Tide Weymouth
40
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsNo

    3.9★

    Good

  • Sykes rating

Sleeps 10, fully renovated 5 storey Georgian sea front house, Large TV, sea views, 3 en-suite bedrooms, less than 50m to the beach. WiFi. (Ref. 1001820)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 3 nights £1478

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A backyard with a hot tub, a table with chairs, an umbrella, grass, trees, and a wooden fence at Cliffwalk Cottage in Southwell
26
Southwell, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

This contemporary holiday home rests in Portland, Dorset. Hot tub. Barbecue. Near amenities. Pet-friendly. Easton 1.5 miles; Chiswell 3 miles; Weymouth 7.5 miles. (Ref. 1122555)

  • Wi-fi
  • Hot Tub
  • Dishwasher
  • Washing machine


for 3 nights £384

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A living room with a sofa, green armchair, round mirrors, dining table with dishes and wine bottle at The Cottage in Weymouth
28
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.1★

    Good

  • Sykes rating

The Cottage is a charming, two-bedroom townhouse resting in Weymouth, Dorset. Close to amenities. Smart TV. Enclosed balcony. Dorchester 8.5 miles; Bridport 20.6 miles. (Ref. 1137088)

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


for 3 nights £562

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The exterior corner of a building with blue beams a glass door partially open and a sign that reads Groves House at Groves House Castletown near Fortuneswell
17
Castletown near Fortuneswell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.2★

    Good

  • Sykes rating

Groves House is a lavish, reverse-level abode located in Castletown near Fortuneswell in Dorset, with an open-plan layout and only a short walk from a pub. Weymouth 5.6 miles. (Ref. 1166808)

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


for 3 nights £464

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A house with solar panels on the roof and a gravel driveway with plants in the foreground at The Old School Cottage in Tincleton near Dorchester
61
Tincleton, Dorset, DT2
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Well-presented barn conversion, close to the rural Dorset hamlet of Tincleton. Country views, underfloor heating, woodburner, Frome Valley walks close by. Dorchester 5 miles. (Ref. 20691)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Dishwasher
  • Washing machine


for 3 nights £305

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