Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 423 cottages

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A wooden hut with an open door and small stairs on a grassy lawn with a picnic table at Acres Meadow in Maiden Newton
21
Maiden Newton, Dorset, DT2
  • Sleeps4
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming shepherd's hut located in the village of Maiden Newton, Dorset. Ideal for a small family. Private meadow. Wood burning stoves. West Bay 13.5 miles; Weymouth 17.1 miles. (Ref. 1157420)

  • Off-road parking
  • Ground floor bedroom


for 7 nights $484

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A balcony with two chairs and a table overlooking a rocky shoreline and the sea at Sunset Lodge in Fortuneswell
27
Fortuneswell, Dorset, DT5
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Sunset Lodge is a lovely retreat on Portland, moments from Chesil beach in Fortuneswell, Dorset, enjoying wonderful coastal views from the a balcony. Weymouth 5.3 miles. (Ref. 1173296)

  • Wi-fi
  • Washing machine
  • Baby-friendly


for 7 nights $1199

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A window view of a coastal town with a sculpture of three whales on the windowsill at Octopus in West Bay
17
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.0★

    Good

  • Sykes rating

A stylish second-floor apartment in the heart of West Bay in Dorset. Great location. Sea views. Open-plan. WiFi. West Bay 0.1 miles; Charmouth 8.5 miles; Lyme Regis 11.3 miles; Seaton 19.9 miles. (Ref. 1106456)

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


for 7 nights $859

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Stone buildings with blue doors and windows beside a grassy field under a clear sky at The Linhay in Bridport
24
Bridport, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4★

    Good

  • Sykes rating

This lovely semi-detached cottage can be found nestled on the outskirts of Bridport, Dorset. Pet-friendly. Open-plan living. Private patio. West Bay 5.3 miles; Lyme Regis 14.4 miles. (Ref. 1102965)

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


for 7 nights $573

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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 7 nights $736

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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 7 nights $2027

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A large apartment building with green-tinted glass balconies and cylindrical glass elevator shafts along a street at Manhattan Beach in Castletown Portland
27
Castletown, Portland, Dorset, DT5
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Manhattan Beach is an apartment with a balcony with sunning sea and marina vistas, on the edge of the village of Castletown, Isle of Portland, in Dorset. Portland 2.2 miles; Weymouth 5.5 miles; Dorchester 12.5 miles. (Ref. 1161472)

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


for 7 nights $796

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A front view of a brick house with a white door and blue garage door and a palm tree in the garden at Milton House in Weymouth
29
Weymouth, Dorset, DT4
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.3★

    Good

  • Sykes rating

A homely, mid-terraced holiday property resting in Weymouth, Dorset. Off-road parking. Pet-free. Close to a beach and amenities. Dorchester 6.6 miles; Bridport 18.2 miles. (Ref. 1116564)

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


for 7 nights $801

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A living room with a small wooden dining table and chairs a round wooden coffee table a fireplace with a mirror above a television on a stand and beige sofas at Seagulls Nest in West Bay
20
West Bay, Dorset, DT6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.0★

    Good

  • Sykes rating

Seagulls Nest is a charming ground-floor apartment situated in the heart of West Bay in Dorset, enjoying an electric fire and close proximity to a beach. Bridport 1.6 miles; Lyme Regis 11.4 miles. (Ref. 1169211)

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


for 7 nights $651

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A patio area with a yellow barbecue grill a dining table with chairs and a wooden fence at Mellstock in Nottington near Weymouth
40
Nottington near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.0★

    Good

  • Sykes rating

Mellstock is a charming property resting in Nottington near Weymouth, Dorset. Dog-friendly. Off-road parking. Shared garden. Barbecue. Family-friendly. Weymouth 3.4 miles; Dorchester 6.4 miles; Fortuneswell 7.1 miles. (Ref. 1105443)

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


for 7 nights $728

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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 7 nights $597

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A corner with two purple chairs and a round glass table by windows with shutters overlooking the beach at High Tide in Weymouth
31
Weymouth, Dorset, DT4
  • Sleeps10
  • Bedrooms5
  • PetsNo

    3.7★

    Good

  • Sykes rating

Beautiful, Georgian seafront house, nestled in the lively town of Weymouth. Sea views. En-suite bedrooms. WiFi. Beach less than 50 metres away. (Ref. 1006583)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights $2027

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A residential building with multiple windows and an entrance on a street with a wooden signpost in front at Flat 30 West Bay
15
West Bay, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2★

    Good

  • Sykes rating

This contemporary, studio-style, fourth-floor apartment sits in West Bay, Dorset. Sea views. Designated parking. Washing machine. Close to amenities and beach. Bridport 1.6 miles; Lyme Regis 11 miles. (Ref. 1058017)

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


for 7 nights $424

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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 7 nights $828

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An outdoor area with a table, bottle and glasses at Sea Spray in Bowleaze
22
Bowleaze, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.2★

    Good

  • Sykes rating

Sea Spray is a pleasant, open-plan holiday home perched on the edge of Bowleaze, Dorset, enjoying sea views and a short walk to a beach and a pub. Weymouth 2.1 miles; Dorchester 6.8 miles; Yeovil 27.5 miles. (Ref. 1174075)

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


for 7 nights $735

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A brick semi detached house with a driveway garage and stairs leading to a gate at Dotties Retreat in Weymouth
46
Weymouth, Dorset, DT4
  • Sleeps6
  • Bedrooms3
  • PetsYes

    3.8★

    Good

  • Sykes rating

Dotties Retreat, a lovely, three-storey abode located in the seaside town of Weymouth, Dorset. Near beach. Off-road parking. Enclosed garden. Pet-friendly. Dorchester 8.7 miles; Bridport 18.8 miles. (Ref. 1157026)

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


for 7 nights $934

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A red brick building with blue doors and white framed windows at Old Malthouse Apartment in Weymouth
18
Weymouth, Dorset, DT4
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.3★

    Good

  • Sykes rating

Old Malthouse Apartment, a practical apartment in the town of Weymouth, Dorset, with a Smart TV and is a short stroll to the beach, harbour, pub and shop. Dorchester 8.1 miles; Bridport 19.3 miles. (Ref. 1175711)

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


for 7 nights $848

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A small white building with a shingled roof and two small trees in pots on either side of the door at Roundham Cottage in West Bay
15
West Bay, Dorset, DT6
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.6★

    Outstanding

  • Sykes rating

A warm and restful converted annex in West Bay, Dorset. Off-road parking. Close to the coast. Bridport 1.5 miles; Lyme Regis 10.9 miles. (Ref. 1067413)

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


for 7 nights $754

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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 7 nights $738

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A wooden house with a gray slate roof and patio furniture in a garden at Bramshurst in Upwey near Weymouth
32
Upwey near Weymouth, Dorset, DT3
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A beautiful terraced holiday home, one of five set around a courtyard, on the edge of Upwey, near Weymouth. Attractive, well-appointed and modern holiday cottage. Many attractions and activities within reach. Weymouth 3.5 miles. (Ref. 932159)

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


for 7 nights $816

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