Upton 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 21 cottages.

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

    Well-presented barn conversion, close to the rural Dorset hamlet of Tincleton. Country views, underfloor heating, woodburner, Frome Valley walks close by. Dorchester 5 miles. (Ref. 20691)

    Last booked yesterday

    7 nights from £288

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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)

    7 nights from £371

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    • Sleeps6
    • Bedrooms3
    • PetsYes

    A charming, semi-detached cottage, on the edge of the village of Tolpuddle. Character, log burner. Quality, well-equipped accommodation. Excellent walking. Dorchester 8 miles. (Ref. 1594)

    7 nights from £326

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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 £332

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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 yesterday

    7 nights from £493

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    • Sleeps4
    • Bedrooms2
    • PetsYes

    Late Victorian former farm cottage, one of two on site, set into the chalk hillside above Dewlish in AONB. With beams, wood floors, en-suite, woodburning stove. Elevated lawned garden, country views. Dorchester 7 miles. (Ref. 927142)

    7 nights from £335

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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 Upton.