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Search results; Over 1,000 homes in Helmsley

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Top guest favourite
Flat in Helmsley
The Flat @ 2 Castlegate
1 bedroom, 1 bed, 1 private bathroom
7–12 Oct, Individual host
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4.98 out of 5 average rating, 230 reviews
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Top guest favourite
Home in Helmsley
Modern spacious fully ensuite house, dog friendly
Individual host
1–6 May
4.99 out of 5 average rating, 94 reviews
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Townhouse in Helmsley
Hyland Cottage
Business host
21–28 Sept
New place to stay
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Superhost
Home in Helmsley
Abbey Cottage, Rievaulx, Near Helmsley, Yorkshire
Business host
12–18 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Cottage in Helmsley
3 Bed in Helmsley (oc-82891)
Business host
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Gilling East
Fairfax View - delightful annexe cottage, Gilling
Individual host
19–24 Oct
4.97 out of 5 average rating, 214 reviews
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Top guest favourite
Home in Harome
Cosy Primrose Cottage, Harome near Helmsley
Business host
15–20 Nov
4.98 out of 5 average rating, 96 reviews
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Top guest favourite
Home in Keldholme
Highfield Annex with off St Parking in Keldholme
Individual host
3–8 Oct
4.99 out of 5 average rating, 119 reviews
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Top guest favourite
Cottage in Wass
Old Bald Peg, North York Moors, character cottage
Individual host
9–14 Oct
5.0 out of 5 average rating, 73 reviews
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Top guest favourite
Cabin in Helmsley
The Coppice Cabin @ Helmsley Meadows
Business host
14–19 Oct
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Place to stay in Osgodby
Long Shed Cottage
Individual host
28 Sept – 3 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Place to stay in Slingsby
The Garden Room
Individual host
20–25 Sept
4.97 out of 5 average rating, 147 reviews
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Top guest favourite
Home in Ampleforth
Lovely family home with a beautiful view
Individual host
2–7 Oct
4.96 out of 5 average rating, 57 reviews
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Top guest favourite
Barn in North Yorkshire
Cosy and luxurious stable conversion
Individual host
25–30 Sept
5.0 out of 5 average rating, 138 reviews
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Top guest favourite
Guest house in Oldstead
Mill House Annex, Oldstead
Individual host
19–24 Sept
5.0 out of 5 average rating, 133 reviews
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Hotel room in Helmsley
Comfortable Ground Floor Ensuite Twin Room
Individual host
6–11 Oct
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Guest favourite
Cottage in Helmsley
Hot Tub & Sauna, Pet-Friendly Cottage in Helmsley
Individual host
30 Oct – 6 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest house in Nether Silton
The Dog House, double en-suite
Individual host
4–9 Oct
4.98 out of 5 average rating, 115 reviews
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Top guest favourite
Cabin in Old Byland
Beck- Luxury, off grid, woodland cabin-streamside
Individual host
30 Sept – 5 Oct
4.96 out of 5 average rating, 85 reviews