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Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 441 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A quaint, white-washed cottage resting in Weymouth, Dorset. Off-road parking. Smart TV. Open-plan living. Xbox. Close to beach. Dorchester 5.2 miles; Bridport 17 miles; Lyme Regis 26.3 miles. (Ref. 1113457)

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

7 nights from $681

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Victorian Semi located in Weymouth, Short walk to Brewers Quay and the Harbour. (Ref. 993971)

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

7 nights from $684

  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

This wonderful renovated cottage is situated in the village of Abbotsbury, near the coastal town of Weymouth, Dorset. Rustic, cosy interior. stove, Weymouth 8.8 miles. (Ref. 992021)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from $786

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Contemporary barn conversion, close to the Dorset coast. Secluded garden. Solid oak flooring. Five minute drive to Weymouth. (Ref. 994207)

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

7 nights from $772

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Dairy Cottage is a delightful, three-bedroom thatched cottage resting on a working farm on the outskirts of Abbotsbury, Dorset. Rural views. Pet-friendly. Stylish. Woodburning stove. Weymouth 12.3 miles. (Ref. 1123043)

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

7 nights from $781

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

This picturesque cottage, situated in the village of Upwey, with parking. Short drive to Weymouth. Close to pub and tea rooms. Lovely walks nearby. (Ref. 994658)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $584

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A wonderful stone cottage set in Langton Herring within the beautiful county of Dorset. Close to the coast. Open fire. Pet friendly. Weymouth 5.7 miles; Isle of Portland 9.6 miles; Dorchester 10 miles. (Ref. 1061319)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Baby-friendly
  • Games room
  • $526 off - Fri 20th Dec to 27th Dec 2024

  • $1341 off - Fri 27th Dec 2024 to 3rd Jan 2025

7 nights from $730

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

Melanie's Cottage is a lovely mews-style holiday home located in Brewers Quay Harbour, Weymouth. Allocated parking. WiFi. Close to beach and amenities. Dorchester 8.5 miles; West Lulworth 17.4 miles. (Ref. 1146011)

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

7 nights from $629

Last booked yesterday
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  • Sleeps6
  • Bedrooms4
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

Spindrift is a characterful, home resting upon Brewers Quay Harbour in Dorset. Original features. Close to amenities, attractions and the harbour. Balcony. Dorchester 8.5 miles; West Lulworth 15.3 miles. (Ref. 1137640)

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

7 nights from $914

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.5

    Outstanding

  • Sykes rating

Lovingly decorated one bedroom property ideal for couples. Wi-Fi. King-size bed in spacious bedroom. Located a short walk away from the beautiful Dorset coast. (Ref. 994630)

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

7 nights from $534

Last booked 2 hours ago
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A stylish property resting in the resort of Weymouth, Dorset. Enclosed garden. Pet free. Beach nearby. Dorchester 10.1 miles; Bridport 18.8 miles. (Ref. 1100742)

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

7 nights from $756

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Beautiful 1 bedroom stable conversion in the heart of the harbour area in Weymouth. WIFI, Close to town centre and beach. Parking for one car. (Ref. 1096825)

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

7 nights from $600

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Tucked in a quiet location in Weymouth, The Pines is a modern holiday home for families or couples. Welcomes two dogs. Pub and shop 10 mins. Beach 1 mile. Dorchester 9 miles. (Ref. 994549)

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

7 nights from $772

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.5

    Outstanding

  • Sykes rating

Delightful terraced cottage. Central Weymouth location. Close to Harbour and beach . sleeping 4. Enclosed garden. WiFi. Weymouth beach just 10 minutes away. (Ref. 998253)

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

7 nights from $681

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    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

7 nights from $757

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.6

    Outstanding

  • Sykes rating

Beautiful and spacious cottage over three floors in Weymouth. Next to the Old Harbour and close to town centre. Beach 1 mile. Pub and shop 5 min. Beach 1 mile. Dorchester 8.5 miles. (Ref. 994354)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $616

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.3

    Good

  • Sykes rating

Tranquil Tides is a well-positioned, ground-floor apartment resting in Weymouth, Dorset. Romantic. Near the beach and amenities. Enclosed courtyard. Pet friendly. Central. Dorchester 7.7 miles; Bridport 20.3 miles. (Ref. 1132772)

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

7 nights from $600

Last booked yesterday
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  • Sleeps6
  • Bedrooms4
  • PetsYes

    4.4

    Good

  • Sykes rating

Lovely 4 bedroom house in gated area. Close to Weymouth harbour. Secure gated parking for one car. Welcomes two dogs. WiFi. (Ref. 994213)

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

7 nights from $963

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

A superb barn conversion resting in Puncknowle near Burton Bradstock, Dorset. WiFi. Balcony. Rural location. Bridport 6.5 miles; Weymouth 12.9 miles; Swanage 38.7 miles. (Ref. 1098014)

  • Wi-fi
  • Washing machine
  • Baby-friendly

7 nights from $757

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.7

    Outstanding

  • Sykes rating

A beautiful and contemporary first-floor apartment overlooking the harbour in Weymouth, Dorset. Balcony with harbour views. Master with en-suite. Allocated parking space. Dorchester 8.4 miles; Bridport 20.5 miles. (Ref. 1059263)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Sat 1st Jun to 31st Aug 2024

7 nights from $851

This collection of Chesil Beach holiday cottages places you by one of Dorset's most iconic landmarks. Forming part of the Jurassic Coast, a UNESCO World Heritage Site, this 18-mile-long shingle barrier beach stretches from West Bay to Portland. Couples and families seeking the great outdoors will delight in this wild and unique natural landscape.

Why Chesil Beach?

The bustling Chesil Beach is lined with cafés, bars and plenty of family-friendly attractions. Head to the Fine Foundation Chesil Beach Centre to learn more about marine life through interactive displays, alongside booking boat trips and wildlife activities! From your Chesil Beach accommodation, you'll have the Fleet Lagoon nature reserve within easy reach to spot birdlife and rare species below the surface. Looking to plan a fishing trip? West Bexington is one of the most popular spots along Chesil Beach for catching mackerel! If beachcombing and swimming are top of your list, visit West Bay and Chesil Cove, two more sheltered and idyllic spots to spend a leisurely day. You are guaranteed unforgettable sunsets and views along the Jurassic Coast, and maybe even dolphins and whales in the distance! For more unmissable things to do at Chesil Beach, visit our Weymouth travel guide.

Places to Visit near Chesil Beach

If you fancy exploring further afield, Chesil Beach holiday cottages make a wonderful base for Dorset! Plenty of activities await in the seaside town of Weymouth, from SEA Life to Weymouth's vibrant harbour, whereas West Bay is a much smaller harbour with spectacular cliffs to behold. You'll also find the nearby Bridport for plenty of cultural attractions in a delightful market town. History lovers can wander through a Roman Town House and Dorset Museum in Dorchester, as well as the former home of Victorian novelist, Thomas Hardy. Alternatively, visit the Isle of Portland for sweeping sea views from the villages of Castletown and Easton.

Types of Holiday

Whether it's a Chesil Beach lodge or luxury apartment, there are a variety of properties to suit all preferences. For seafarers and sandcastle makers, browse this selection of Dorset coastal cottages for easy access to the beach. Country cottages in Dorset are a wonderful alternative if you'd prefer to be nestled in the heathland, forests and rolling hills. Hoping to bring your furry friends along to the dog-friendly Chesil Beach? Explore a variety of dog-friendly cottages in Dorset, whilst these luxury cottages in Dorset are extra-special retreats. If your holiday date is looming, don't worry, there are a range of last minute cottages in Dorset to choose from!