Castletown Holiday Cottages

Your search returned 20 cottages.

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
    • 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 £342

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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)

    Great for families

    7 nights from £438

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    • Sykes Rating
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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)

    Great for groups

    7 nights from £531

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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)

    Great for families

    7 nights from £395

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    • Sykes Rating
    • 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)

    Last booked yesterday

    7 nights from £375

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    • Sykes Rating
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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)

    Great for families

    7 nights from £489

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    • Sykes Rating
    • Sleeps4
    • Bedrooms3
    • PetsNo

    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 £303

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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 £357

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    • Sykes Rating
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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 within the last 2 days
    Great for families

    7 nights from £489

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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 £308

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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.