Helmsley Cottages from ₩552,731 | Expedia

A historic castle ruin with two towers on a grassy hill.

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Nov 20 - Nov 22

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Nov 27 - Nov 29

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Dec 11 - Dec 13

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Map of Helmsley

Our top choices for Helmsley cottages

A stone building with a gabled roof, a green door, and a window with white shutters.

1. 29 Bondgate

York

₩977,053 total

includes taxes & fees

Nov 18 - Nov 19

A stone house with a red-tiled roof, a blue door, and a narrow stone pathway leading to the entrance.

2. Cliff House

York

₩1,000,884 total

includes taxes & fees

Nov 18 - Nov 19

A two-story stone house with a red-tiled roof, a wooden fence, and a paved driveway.

3. Lilac Cottage

York

United States

Kevin

₩663,284 total

includes taxes & fees

Nov 23 - Nov 24

A traditional thatched-roof cottage with a green door, white walls, and a small garden with pink flowers.

4. Holly Cottage

York

₩1,306,710 total

includes taxes & fees

Nov 26 - Nov 27

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Learn more about Helmsley

Nestled in North Yorkshire, this charming market town invites exploration of its medieval castle ruins and the National Centre for Birds of Prey. Wander cobblestone streets lined with independent shops before hiking scenic trails through the surrounding North York Moors.

See all hotels in Helmsley

A historic castle ruin with two towers on a grassy hill.