Chesil Holiday Cottages

Your search returned 22 cottages.

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    • 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)

    Last booked yesterday

    7 nights from £365

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    • 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)

    7 nights from £438

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    • Sykes Rating
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    • Sleeps4
    • Bedrooms2
    • PetsNo

    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)

    7 nights from £438

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    • Sleeps6
    • Bedrooms3
    • PetsNo

    A quality semi-detached holiday home, one of five in a courtyard location, close to Weymouth. En-suite, modern features. Dog-friendly. Shop and pub within walking distance. Weymouth 3.5 miles. (Ref. 932160)

    7 nights from £489

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    • 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)

    Last booked yesterday

    7 nights from £489

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    Welcoming detached cottage in Weymouth, just over a mile from the seafront. Cosy accommodation with large enclosed garden. Well placed for exploring the coastline and countryside of Dorset. (Ref. 7688)

    7 nights from £390

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    • Sleeps2
    • Bedrooms1
    • PetsNo

    Cosy, detached stone cottage, in Dorset village of Upwey. Elevated site, lovely rural views. Eaves bedroom, conservatory. Private patio. Tea room and lovely walks nearby. Easy drive to the coast. Dorchester 5 miles. (Ref. 943806)

    7 nights from £308

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Gorgeous, semi-detached, Grade II listed 17th century thatched cottage in the Dorset village of Upwey. Quality accommodation with WiFi. Full of original features. Woodburning stove. Dog-friendly. Weymouth 4 miles. (Ref. 916915)

    7 nights from £403

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    • Sleeps5
    • Bedrooms3
    • PetsYes

    A charm-filled terraced cottage set in the stunning village of Upwey in Dorset. Pet-friendly. Dorset AONB. Weymouth 4 miles. (Ref. 972855)

    7 nights from £350

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    A semi-detached Victorian family house in Weymouth. Well-presented and comfortable holiday accommodation. Enclosed garden. Close to harbour and beaches. Weymouth beaches 15 mins walk. Dorchester 7 miles. (Ref. 912573)

    7 nights from £378

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Stunning detached bungalow, beside Dorset's Chesil Beach and South West Coast Path. Unrivalled sea views. Luxuriously appointed throughout. Private gardens. Conservatory. Eight-seater hot tub. Abbotsbury 3 miles, Bridport 6 miles. (Ref. 933164)

    7 nights from £537

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Spacious modern ground floor apartment, situated a short walk from the beach at Preston on the edge of Weymouth. Well presented, comfortable holiday accommodation. En-suite facilities. Superb coastal base. Weymouth 1 mile. (Ref. 938132)

    Last booked within the last 2 days

    7 nights from £392

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    • Sykes Rating
    • Sleeps5
    • Bedrooms3
    • PetsYes

    Attractive semi detached holiday home, residential area on the edge of Weymouth. Well equipped and furnished. Pet friendly. WiFi. Local facilities nearby. Close to beach. Weymouth 1mile. (Ref. 932957)

    7 nights from £341

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    Fully furnished detached house just 1.5 miles from Weymouth and the coast. Three large bedrooms, a kitchen and living area. Nearby Jurassic Coast, Monkey World and Tank Museum. (Ref. 952891)

    Last booked yesterday

    7 nights from £334

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    • Sykes Rating
    • Sleeps4
    • Bedrooms3
    • PetsYes

    This end-terrace cottage dates back to 1792 and is set in the village of Preston, one mile from Weymouth. Ground floor bedroom, pet-friendly, enclosed garden. (Ref. 940157)

    7 nights from £299

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    • Sleeps5
    • Bedrooms3
    • PetsNo

    Comfortable, detached chalet dormer bungalow within the village of Easton on Portland. Well-appointed with enclosed garden. Near local amenities. Ideal for exploring Dorset's Jurassic Coast. Weymouth 6 miles. (Ref. 28523)

    7 nights from £357

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    • Sleeps8
    • Bedrooms5
    • PetsYes

    Quietly situated down a narrow lane in the hamlet of Wakeham on the Isle of Portland. Sea views from the second floor sitting room and master bedroom. Pet-friendly. Woodburning stoves. Portland 2.3 miles. (Ref. 934291)

    Last booked 9 hours ago

    7 nights from £531

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    A grade II listed converted school near the town of Dorchester in Dorset. En-suite. Exposed wooden beams. Dorchester 3 miles. (Ref. 930956)

    7 nights from £455

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    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)

    Last booked yesterday

    7 nights from £571

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    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)

    Last booked within the last 2 days

    7 nights from £581

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    • Sleeps9
    • Bedrooms5
    • PetsNo

    A fresh, detached cottage based in the village of Burton Bradstock in Dorset. En-suite. Jurassic Coast. Distance sea views. Dorset AONB. (Ref. 963177)

    Last booked yesterday

    7 nights from £731

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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Luxury barn conversion in Charminster. Quality accommodation with beams and en-suites. Adjacent golf course. Excellent walking in heart of Hardy's Wessex. Dorchester 1.5 miles. (Ref. 1440)

    Last booked within the last 2 days

    7 nights from £425

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Please find below a selection of self catering holiday cottages to rent in or near Chesil.