Castletown Holiday Cottages

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All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

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    • Sykes Rating
    • Sleeps3
    • Bedrooms1
    • PetsYes

    A welcoming cottage based on the outskirts of Osmington in Dorset. Open-plan. Dorset AONB. Near Dorchester. (Ref. 987459)

    Last booked today

    7 nights from £249

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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)

    Last booked yesterday

    7 nights from £347

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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)

    Last booked today

    7 nights from £403

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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 £489

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    • Sykes Rating
    • 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)

    7 nights from £315

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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)

    7 nights from £394

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    • Sykes Rating
    • 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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    • 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 £438

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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

    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 today

    7 nights from £557

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All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

*Applicable to holidays commencing at least 6 weeks in the future. Full balance due 6 weeks prior to departure. Please refer to Book Now Pay Later Terms and Conditions for further information.

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