Chesil Cottage Holidays
British Travel Award Winners!
We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.
24/7 “On Holiday” Support
Our friendly UK team are here to help, in case of any emergency.
Award Winning Holiday Experts
Over 30 years of experience in UK self-catering holidays.
B Corp Certified Business
Committed to making a positive social and environmental impact.
Safe & Secure Payments
Flexible payment options for peace of mind.
Your Chesil Beach, Dorset search returned 436 cottages
- Sleeps4
- Bedrooms2
- PetsYes
A characterful, thatched cottage resting in Langton Herring near Chickerell, Dorset. Original features. Close to amenities. Dorset AONB. Pet-friendly. Abbotsbury 4.5 miles; Weymouth 5.8 miles; Portland 9.3 miles; Dorchester 9.7 miles. (Ref. 1123272)
- Wi-fi
- Baby-friendly
7 nights from £560
- Sleeps5
- Bedrooms2
- PetsYes
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
-
£421 off - Fri 20th Dec to 27th Dec 2024
-
£1073 off - Fri 27th Dec 2024 to 3rd Jan 2025
7 nights from £591
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps9
- Bedrooms5
- PetsYes
A charming cottage situated on a working farm within the hamlet of Rodden near Abbotsbury. Outstanding scenery. Woodburning stove. Weymouth 7.4 miles; Dorchester 9.4 miles; West Bay 11.7miles. (Ref. 1050484)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £1029
- Sleeps6
- Bedrooms3
- PetsNo
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 £636
- Sleeps4
- Bedrooms2
- PetsNo
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 £627
- Sleeps4
- Bedrooms2
- PetsNo
123 On The Sea is a lovely, two-bedroom apartment residing in Weymouth, Dorset. Near Dorset AONB. Sea views. Close to amenities and a beach. Private balcony. Off road parking. Dorchester 7.3 miles; Bridport 18.9 miles. (Ref. 1133961)
- Wi-fi
- Off-road parking
- Dishwasher
7 nights from £562
- Sleeps6
- Bedrooms3
- PetsYes
A stylish and contemporary period home near Brewers Quay, Weymouth. Stylish. Close to beach. Courtyard with furniture. Close to local amenities. Dorchester 8.4 miles; Bridport 22.1 miles. (Ref. 1109892)
- Wi-fi
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £650
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps4
- Bedrooms2
- PetsYes
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 £613
- Sleeps2
- Bedrooms1
- PetsNo
A beautiful, second-floor apartment overlooking the harbour in Weymouth, Dorset. Romantic. Sea views. Close to beach. Close to local amenities. Dorchester 8.3 miles; Bridport 19.1 miles. (Ref. 1107011)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £472
- Sleeps4
- Bedrooms2
- PetsYes
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
7 nights from £613
- Sleeps6
- Bedrooms3
- PetsYes
Superb, modern semi-detached holiday cottage, one of five on-site, on the edge of the Dorset village of Upwey, near Weymouth. Tastefully furnished. En-suite, Smart TVs. Dog-friendly. Short drive to Weymouth beach. Weymouth 3.5 miles. (Ref. 932161)
- Wi-fi
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £691
- Sleeps4
- Bedrooms2
- PetsYes
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 £613
- Sleeps6
- Bedrooms3
- PetsNo
A beautifully presented property just moments from Weymouth harbour and Netwon's Cove in Dorset. Near amenities. WiFi. Off-road parking. En-suite. Isle of Portland 6.1 miles; Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1056258)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
7 nights from £722
- Sleeps2
- Bedrooms1
- PetsNo
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
-
£200 off - Fri 26th Jul to 30th Aug 2024
7 nights from £521
Book your 2024 holiday with peace of mind by adding Flexible Cancellation
- Sleeps6
- Bedrooms3
- PetsNo
Situated in the beautiful Bowleaze Cove area of Weymouth, just seconds from a beach is this enchanting holiday home. (Ref. 994020)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £1142
- Sleeps4
- Bedrooms1
- PetsNo
Centrally located, near to Weymouth harbour. Sleeps 4. Patio and off road parking. Close to bars and restaurants. (Ref. 994563)
- Wi-fi
- Off-road parking
- Washing machine
7 nights from £413
- Sleeps4
- Bedrooms2
- PetsNo
A superb two-bedroom apartment resting in Weymouth, Dorset. Opposite beach. Sea views. Close to amenities. Dorchester 7.4 miles; Bridport 18.8 miles. (Ref. 1053562)
- Wi-fi
- Ground floor bedroom
- Washing machine
7 nights from £631
- Sleeps4
- Bedrooms2
- PetsNo
Charming Edwardian terraced cottage located close to Sansfoot castle in Weymouth. Near to shops and town centre. Beach 10 minutes away. WiFi. Dorchester 8.5 miles. (Ref. 994072)
- Wi-fi
- Dishwasher
- Washing machine
7 nights from £506
- Sleeps8
- Bedrooms4
- PetsYes
Detached chalet bungalow in West Bexington, Dorset. Large garden with sea views. Close to beach. WiFi. Abbotsbury 4.8 miles; Bridport 6.8 miles. (Ref. 1017936)
- Wi-fi
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
7 nights from £1240
- Sleeps2
- Bedrooms1
- PetsNo
A lovely one-bedroom holiday home perched on the outskirts of Weymouth, Dorset. Romantic. Near a beach. Pet-free. Close to amenities. Dorchester 8.8 miles; Bridport 19.6 miles. (Ref. 1114655)
- Wi-fi
7 nights from £518
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!