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Search results; Over 1,000 places in Helmsley

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Guest favorite
Home in Helmsley
31 Bridge Street
6 guests3 bedrooms4 beds2.5 baths
Mar 18 – 23
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Mar 18 – 23
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$210 per night

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Cottage in Helmsley
Clothes Prop Cottage, a Helmsley hideaway
Free cancellation
Jun 23 – 28
$132 per night
4.94 out of 5 average rating, 253 reviews
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Vacation home in Helmsley
Honeysuckle Cottage
Free cancellation
Mar 23 – 28
$147 per night
4.84 out of 5 average rating, 49 reviews
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Apartment in Helmsley
The Flat @ 2 Castlegate
Free cancellation
Apr 11 – 16
$110 per night
4.98 out of 5 average rating, 175 reviews
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Home in Helmsley
Modern spacious fully ensuite house, dog friendly
Free cancellation
Apr 21 – 26
$212 per night
5.0 out of 5 average rating, 70 reviews
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Cottage in Helmsley
Romantic Cottage with Hot Tub & Countryside Views
Free cancellation
Apr 16 – 21
$426 per night
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Helmsley
Idyllic 300 year old bijoux stone country cottage
1 double bed
Mar 31 – Apr 5
$142 per night
4.84 out of 5 average rating, 187 reviews
Top guest favorite
Tiny home in Helmsley
Luxury Studio Haven in Helmsley
1 double bed
Mar 16 – 21
$149 per night
5.0 out of 5 average rating, 26 reviews
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Vacation home in Helmsley
Garden Cottage - Peaceful in the Heart of Helmsley
1 double bed
Mar 16 – 21
$155 per night
4.82 out of 5 average rating, 76 reviews
Barn in Helmsley
Little Barn, Helmsley
1 bed
Apr 11 – 16
$168 per night
New place to stay
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Cottage in Helmsley
Holiday cottage in lovely Helmsley
Free cancellation
Jul 26 – 31
$149 per night
4.79 out of 5 average rating, 19 reviews
Superhost
Cottage in Helmsley
Sunshine Cottage
3 king beds
Mar 28 – Apr 2
$311 per night
New place to stay
Superhost
Train in Helmsley
Unique Railway Carriage - In the Heart of Helmsley
3 beds
Mar 16 – 21
$194 per night
4.87 out of 5 average rating, 193 reviews
Cottage in Helmsley
Bridge House
3 beds
Apr 26 – May 3
$107 per night
4.77 out of 5 average rating, 13 reviews
Home in Helmsley
Ivy Cottage Helmsley
4 beds
Mar 23 – 28
$128 per night
New place to stay
Guest favorite
Cottage in Helmsley
3 Bed in Helmsley (82891)
4 beds
Apr 25 – 30
$200 per night
5.0 out of 5 average rating, 5 reviews
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Cottage in East End
The Owlets, Ampleforth
2 king beds
Mar 24 – 29
$137 per night
4.99 out of 5 average rating, 284 reviews
Home in Helmsley
Host & Stay | Willow Cottage
2 beds
Apr 16 – 21
$212 per night
4.77 out of 5 average rating, 64 reviews
Guest favorite
Cottage in Helmsley
Rye Cottage
4 beds
May 2 – 7
$316 per night
5.0 out of 5 average rating, 22 reviews