Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 428 cottages

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  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern and well-furnished Hops House is an ideal family holiday home in Weymouth. WiFi. Pub and shop 5 min. Beach 1 mile. Dorchester 9 miles. (Ref. 994277)

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


for 7 nights €895

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.2

    Good

  • Sykes rating

A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1111030)

  • Wi-fi
  • Dishwasher


for 7 nights €739

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Stylish semi-detached holiday cottage, one of five on-site, in Dorset's River Wey Valley, on the edge of Upwey near Weymouth. Open plan living, en-suite facilities, private patio. Furnished and equipped to a very high standard. Weymouth 3.5 miles. (Ref. 932157)

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


for 7 nights €701

  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Anchor Cottage is a delightful, terraced home resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Family-friendly. Dorchester 7.6 miles; West Bay 17.8 miles. (Ref. 1150151)

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


for 7 nights €619

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms4
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

This charming, four-bedroom holiday home rests in Weymouth, Dorset. Over three floors. Open plan. Off-road parking. Dorchester 8.5 miles; Bridport 19.2 miles. (Ref. 1043677)

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


for 7 nights €1570

  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Perfect

  • Sykes rating

The Halt is a delightful, romantic holiday annex situated in the lovely little village of Maiden Newton in Dorset with a studio-style living space. West Bay 12.2 miles; Weymouth 17.2 miles; Lyme Regis 22.7 miles (Ref. 1165359)

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


for 7 nights €411

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.4

    Good

  • Sykes rating

Modern, bright apartment with sea views over to Weymouth Bay. Short walk to the beach and a casual stroll to the town centre. Wifi and off-road parking. Great base for exploring Weymouth and the surrounding areas. (Ref. 1098447)

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


for 7 nights €791

  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Comfortable renovated cottage with rear garden and close to the town centre. Garden with furniture. Pub 5 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994191)

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


for 7 nights €706

Last booked yesterday
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  • Sleeps5
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

Directly on the seafront. First floor period apartment. Bright and comfortable. Breath-taking sea views. En-suite shower room. WiFi. Off road parking with garage. (Ref. 993989)

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


for 7 nights €799

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

Bright contemporary property perfect groups of guests in the Isle of Portland. Sea views. WiFi. Shop 10 min. Pub 5 min. Beach 5 min. Weymouth 4.9 miles. (Ref. 994754)

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


for 7 nights €896

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Footprint a converted stable located in a gated development in Weymouth close to harbour and beach. En-suite master bedroom. Beach 1 mile. Dorchester 9 miles. (Ref. 994201)

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


for 7 nights €809

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

An enchanting refurbished cottage in the centre of the lovely village of Sutton Poyntz. Fully furnished and comfortable. Sunny patio garden. WiFi. Weymouth 4 miles. (Ref. 994009)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €527

  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Beautiful coastal views. Off road parking for 3 cars. Beaches a short walk away. WiFi. Perfect for a group of friends for a getaway from the busy lifestyles. (Ref. 994051)

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


for 7 nights €2656

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

A desirable second-floor apartment close to West Bay in the heart of Dorset. Flexible accommodation. Lift access. WiFi. Open-plan. Harbour Views. West Bay 0.1 miles; Bridport 2 miles; Seatown 5.3 miles; Lyme Regis 11.4 miles. (Ref. 1106615)

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


for 7 nights €905

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Winkle Cottage is a wonderful holiday home, set over three floors, situated in the popular coastal town of Weymouth in Dorset by the historic harbour. Dorchester 8.5 miles; Bridport 19.3 miles. (Ref. 1140944)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 5% off - Fri 3rd Apr to 2nd May 2026


for 7 nights €780

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodation with sensational sea views. Shared access to Lighthouse observatory. Shared use of heated pool and Jacuzzi. (Ref. 12497)

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


for 7 nights €702

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.6

    Outstanding

  • Sykes rating

The Corner House is a delightful terrace home resting in the popular seaside town of Weymouth, Dorset. Close to amenities. Near beach. Enclosed courtyard. Dorchester 7.1 miles; Bridport 19.1 miles. (Ref. 1129331)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights €657

  • Sleeps8
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A charming terraced property resting in Fortuneswell, Dorset. Sea views. WiFi. Terrace garden. Pet-friendly. Weymouth 5.2 miles. (Ref. 1035417)

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


for 7 nights €565

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic Coast. Amazing views. Shared access to lighthouse observatory. Shared use of seasonal outdoor heated pool and Jacuzzi. (Ref. 12494)

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


for 7 nights €779

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

This lovely property rests in the pretty village of Shipton Gorge, Dorset. Countryside views. Ground-floor accommodation. WiFi. Bridport 2.6 miles. West Bay 4.1 miles. (Ref. 1020427)

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


for 7 nights €798