Chesil Holiday Cottages

All cottages available for only £25 Deposit!*

For a limited time only, all our cottages can be reserved for only £25 Deposit. Don't miss out!

Your search returned 20 cottages.

    • Sykes Rating
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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 5 hours ago

    7 nights from £394

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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 £412

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    • Sykes Rating
    • 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 £412

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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)

    7 nights from £429

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    • Sykes Rating
    • 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 £429

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    • Sykes Rating
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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 £339

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    • Sykes Rating
    • 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 £269

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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 £359

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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 £337

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

    Well-presented, modern semi-detached Weymouth cottage. Established residential area near Weymouth beach and station. WiFi. Smart TV. Sole use of 5 seater hot tub! Perfect Dorset coastal holiday choice. Dorchester 7 miles. (Ref. 937704)

    7 nights from £360

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All cottages available for only £25 Deposit!*

For a limited time only, all our cottages can be reserved for only £25 Deposit. Don't miss out!

*Please refer to £25 deposit offer terms & conditions for further information.

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