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Chesil Cottage Holidays

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Your Chesil Beach, Dorset search returned 440 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Garland is a delightful abode 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. 1105442)

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

7 nights from €674

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

Alice's Cottage is a characterful, thatched cottage situated in Burton Bradstock, Dorset. Pet-friendly. Amenities and beach nearby. Lawned garden. Bridport 3.3 miles; Weymouth 15.4 miles. (Ref. 1144638)

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

7 nights from €899

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Little Gull Cottage is a lovely, three-storey holiday home close to Weymouth’s harbour in Dorset. Patio with furniture. Close to amenities. Smart TV. Dorchester 8.2 miles; Bridport 18.7 miles. (Ref. 1144645)

  • Wi-fi
  • Baby-friendly

7 nights from €653

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Chickerell House is a pleasant, detached holiday home resting in the seaside town of Weymouth, Dorset. Ground-floor living. Near to shop and pub. En-suite. Dorchester 8.5 miles; Bridport 17.5 miles. (Ref. 1152691)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • 20% off - Fri 29th Mar to 6th Apr 2024

7 nights from €782

  • Sleeps5
  • Bedrooms3
  • PetsYes
  • Sykes rating

Norden Cottage is a fine, three-bedroom abode resting in Osmington, Dorset. Woodburning stove. Pet-friendly. Enclosed garden. Close to amenities. Weymouth 4.9 miles. (Ref. 1149647)

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

7 nights from €672

Last booked 2 days ago
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  • Sleeps8
  • Bedrooms5
  • PetsYes
  • Sykes rating

Victorian Town House is a large, coastal property resting in the seaside town of Weymouth, Dorset. Close to a shop, a pub, and a beach. Large property. Dorchester 7.5 miles; West Bay 17.5 miles. (Ref. 1035186)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from €842

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes
  • Sykes rating

The Nightingale is a stylish, semi-detached holiday home resting in Weymouth, Dorset. Designated parking. Close to a beach and amenities. Enclosed garden. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1133998)

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

7 nights from €561

  • Sleeps2
  • Bedrooms1
  • PetsNo
  • Sykes rating

The Apple Loft at Jordan House is a contemporary cottage resting in Bowleaze, on the outskirts of Weymouth, Dorset. Off-road parking. Open-plan. Garden. Dorchester 6.1 miles; Abbotsbury 9.8 miles; Bridport 19.3 miles. (Ref. 1149531)

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

7 nights from €638

  • Sleeps8
  • Bedrooms5
  • PetsYes
  • Sykes rating

Glyde House is a detached property situated in Dorchester, Dorset. Close to a shop and a pub. Off-road parking. Garden. Near Dorset AONB. Weymouth 8.6 miles; Isle of Portland 14.7 miles. (Ref. 1150284)

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

7 nights from €1131

  • Sleeps5
  • Bedrooms3
  • PetsNo
  • 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

7 nights from €624

  • Sleeps8
  • Bedrooms4
  • PetsYes
  • Sykes rating

Salt Tides is a stylish, three-storey holiday home resting in Weymouth, Dorset. Enclosed courtyard. Pet-friendly. Close to amenities and the beach. Dorchester 8.1 miles; Bridport 18.8 miles. (Ref. 1141124)

  • Wi-fi
  • Dishwasher

7 nights from €947

  • Sleeps6
  • Bedrooms3
  • PetsYes
  • Sykes rating

Chenies is a traditional cottage in the delightful hamlet of Osmington Mills near Preston, Dorset. Sea views. Near a pub. Characterful. Open fire. Preston 2.8 miles; Weymouth 5.9 miles. (Ref. 1149628)

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

7 nights from €599

  • Sleeps9
  • Bedrooms4
  • PetsNo
  • Sykes rating

Bay Cottage is a well-presented, three-storey detached house situated in the resort of Weymouth, Dorset. Smart TV. Decking with furniture. Near a beach. Dorchester 8.4 miles; Bridport 20.3 miles. (Ref. 1139723)

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

7 nights from €1111

  • Sleeps4
  • Bedrooms2
  • PetsNo
  • Sykes rating

3 Compass Point is a stylish, ground-floor apartment resting in Weymouth, Dorset. Near beach and amenities. Contemporary. Open-plan. Private parking. Dorchester 6.7 miles; Bridport 20.5 miles. (Ref. 1129014)

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

7 nights from €722

Last booked yesterday
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  • 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
  • €493 off - Fri 20th Dec to 27th Dec 2024

  • €1255 off - Fri 27th Dec 2024 to 3rd Jan 2025

7 nights from €678

  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

A charming reverse-level cottage in the village of Upwey, Dorset. Close to amenities. Woodburning stove. In an Area of Outstanding Natural Beauty. Romantic. Walkers & Cyclists. Weymouth 4.5 miles; Dorchester 4.6 miles. (Ref. 1072756)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • €234 off - Fri 26th Jul to 30th Aug 2024

7 nights from €607

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

A lovely two-bedroom, ground-floor apartment resting in Weymouth, Dorset. Near a beach. Close to amenities. Romantic. Ground-floor. Dorchester 7.5 miles; Bridport 20.5 miles. (Ref. 1083146)

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

7 nights from €756

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.8

    Outstanding

  • Sykes rating

2-minute walk to Sandsfoot beach and the South West Coast path. Uninterrupted sea views to Portland and beyond, sleep 5, parking. (Ref. 994582)

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

7 nights from €808

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.4

    Good

  • Sykes rating

Stunning semi-detached holiday cottage in courtyard setting, on the edge of Upwey, near Weymouth. Very high standard of accommodation with en-suite facilities and vaulted ceiling. Dog-friendly, plenty to see and do in the area. Weymouth 3.5 miles. (Ref. 932158)

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

7 nights from €620

Last booked yesterday
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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!