Castletown Holiday Cottages

Your search returned 19 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
    • Sleeps2
    • Bedrooms1
    • PetsNo

    Cosy, detached stone cottage, in Dorset village of Upwey. Elevated site, lovely rural views. Eaves bedroom, conservatory... (Ref. 943806)

    7 nights from £299

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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 b... (Ref. 940157)

    Last booked yesterday

    7 nights from £303

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    • Sykes Rating
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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 pr... (Ref. 938132)

    7 nights from £359

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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, ... (Ref. 932159)

    7 nights from £365

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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 ... (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 Weym... (Ref. 932157)

    7 nights from £438

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    • Sykes Rating
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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Gorgeous, semi-detached, Grade II listed 17th century thatched cottage in the Dorset village of Upwey. Quality accommoda... (Ref. 916915)

    Last booked yesterday
    • 20% off - Sat 31st Mar to 7th Apr 2018

    7 nights from £403

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    • Sykes Rating
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    • Sleeps4
    • Bedrooms2
    • PetsNo

    Charming detached Grade II listed lighthouse cottage at Portland Bill on Dorset's Jurassic Coast. Upside down accommodat... (Ref. 12497)

    Last booked within the last 2 days

    7 nights from £567

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    • Sykes Rating
    • Sleeps4
    • Bedrooms2
    • PetsNo

    Delightful, single-storey, Grade II listed cottage linked to Old Higher Lighthouse at Portland Bill on Dorset's Jurassic... (Ref. 12494)

    Last booked yesterday

    7 nights from £550

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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)

    7 nights from £350

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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 £20 deposit offer terms & conditions for further information.

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