Search results; Over 1,000 places in Helmsley

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Guest favorite
Vacation home in Helmsley
Honeysuckle Cottage
4 guests2 bedrooms3 beds1 bath
Aug 25 – 30
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Aug 25 – 30
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R19,697 ZAR for 5 nights
for 5 nights

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Top guest favorite
Cottage in Helmsley
Clothes Prop Cottage, a Helmsley hideaway
Free cancellation
Jun 23 – 28
R14,377 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 260 reviews
Top guest favorite
Apartment in Helmsley
The Flat @ 2 Castlegate
Free cancellation
Aug 18 – 23
R12,221 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 184 reviews
Top guest favorite
Tiny home in Helmsley
Luxury Studio Haven in Helmsley
1 double bed
Jun 8 – 13
R16,966 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 34 reviews
Shepherd’s hut in Helmsley
The Helmsley Hut
1 double bed
Jun 9 – 14
R11,071 ZAR for 5 nights
for 5 nights
New place to stay
Top guest favorite
Cottage in Helmsley
Sunshine Cottage
3 king beds
Jun 6 – 11
R35,253 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Superhost
Vacation home in Helmsley
Garden Cottage - Peaceful in the Heart of Helmsley
1 double bed
Jun 15 – 20
R17,685 ZAR for 5 nights
for 5 nights
4.8 out of 5 average rating, 81 reviews
Guest favorite
Home in Helmsley
Idyllic 300 year old bijoux stone country cottage
1 double bed
Jul 21 – 26
R15,816 ZAR for 5 nights
for 5 nights
4.85 out of 5 average rating, 193 reviews
Top guest favorite
Cottage in Helmsley
Romantic Cottage with Hot Tub & Countryside Views
Free cancellation
Jul 20 – 25
R34,982 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 24 reviews
Superhost
Cottage in Helmsley
Holiday cottage in lovely Helmsley
Free cancellation
Jul 12 – 17
R16,966 ZAR for 5 nights
for 5 nights
4.79 out of 5 average rating, 19 reviews
Top guest favorite
Home in Helmsley
Central Fully Ensuite house sleeps 6 dog friendly
Free cancellation
Sep 15 – 20
R22,429 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 94 reviews
Guest favorite
Cottage in Helmsley
The Byre
1 double bed
Sep 27 – Oct 2
R9,556 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Superhost
Train in Helmsley
Unique Railway Carriage - In the Heart of Helmsley
3 beds
Jun 3 – 8
R21,997 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 195 reviews
Barn in Helmsley
Little Barn Helmsley
1 king bed
Jun 22 – 27
R17,397 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 4 reviews
Top guest favorite
Home in Harome
Petite cosy Cottage in beautiful village location
3 beds
Jun 8 – 13
R16,102 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Helmsley
31 Bridge Street
4 beds
Sep 4 – 9
R24,010 ZAR for 5 nights
for 5 nights
4.9 out of 5 average rating, 145 reviews
Home in Helmsley
Host & Stay | Willow Cottage
3 beds
Jun 16 – 21
R22,548 ZAR for 5 nights
for 5 nights
4.78 out of 5 average rating, 68 reviews
Guest favorite
Cottage in Helmsley
Pretty Yorkshire Stone Cottage Harome
3 beds
Jun 8 – 13
R20,992 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 94 reviews
Guest favorite
Cottage in Helmsley
3 Bed in Helmsley (82891)
4 beds
Jun 13 – 18
R19,378 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 6 reviews