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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Browse Select Helmsley Holiday Homes

Host Stay Park View
House

Host Stay Park View

2.0 star property
8.0 out of 10, Very good, (3)
"Excellent in every way possible. Clean warm and beautiful "
Host Stay Park View
Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI
Property grounds

Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI

10.0 out of 10, Exceptional, (21)
"Lovely, clean and tidy property in a good location. Would stay again."
Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI
Host & Stay | Lavender Cottage
Fridge, microwave, oven, electric kettle

Host & Stay | Lavender Cottage

10.0 out of 10, Exceptional, (2)
"My husband, toddler, and greyhound stayed for three nights in this lovely cottage. It was quiet and cozy, with all the amenities we needed. The location was perfect for accessing the train station and pub. Our dog was also very comfortable—the house did not smell of pets. It had been cleaned very well. "
Host & Stay | Lavender Cottage
Host & Stay | Rose Cottage
Fireplace

Host & Stay | Rose Cottage

9.6 out of 10, Exceptional, (4)
"Very enjoyable stay in a surprisingly roomy terraced property. Quiet location yet very close to centre of Stokesley. High standard of cleaning and equipment. Our only issues were directions to the property, key in the wrong place and a microwave problem. We believe all of these points are being addressed."
Host & Stay | Rose Cottage
Host & Stay | Damson Cottage
Fridge, microwave, oven, stovetop

Host & Stay | Damson Cottage

8.0 out of 10, Very good, (1)
Host & Stay | Damson Cottage
Host Stay Grange Cottage
House

Host Stay Grange Cottage

2.0 star property
Host Stay Grange Cottage
18 Horner Street York
House | Private kitchen

18 Horner Street York

3.0 star property
9.2 out of 10, Wonderful, (9)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
The price is £383
includes taxes & fees
6 Aug - 7 Aug
18 Horner Street York
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
7 bedrooms, iron/ironing board, travel cot, free WiFi

Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

9.8 out of 10, Exceptional, (29)
"We had a fantastic time at this property! The owners were incredibly helpful and the facilities and location were superb. Would highly recommend for a large group looking for a fun country escape!"
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
Host Stay Finch House
House

Host Stay Finch House

2.0 star property
The price is £494
includes taxes & fees
12 Aug - 13 Aug
Host Stay Finch House
🌾Luxury Barn Escape with Sauna & Cold Plunge | Sleeps 8 | Near York 🧖‍♀️🦙🌳
Terrace/patio

🌾Luxury Barn Escape with Sauna & Cold Plunge | Sleeps 8 | Near York 🧖‍♀️🦙🌳

10.0 out of 10, Exceptional, (117)
"Fantastic stay"
🌾Luxury Barn Escape with Sauna & Cold Plunge | Sleeps 8 | Near York 🧖‍♀️🦙🌳
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast
Property grounds

Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

10.0 out of 10, Exceptional, (8)
"We enjoyed a lot our stay in this "
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast
Vavasour - a cosy two bedroom historic cottage on the Red House Estate near York
Interior

Vavasour - a cosy two bedroom historic cottage on the Red House Estate near York

Vavasour - a cosy two bedroom historic cottage on the Red House Estate near York
Host Stay Fawcett Cottage
House | Iron/ironing board

Host Stay Fawcett Cottage

3.0 star property
Host Stay Fawcett Cottage
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Fridge, microwave, oven, stovetop

Luxury retreat for 2 couples/ family in spectacular location in North York Moors

10.0 out of 10, Exceptional, (38)
"Loved the location and the property was lovely. We would return again!"
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Spacious period property on historic, private estate with seasonal, outdoor pool
Exterior detail

Spacious period property on historic, private estate with seasonal, outdoor pool

10.0 out of 10, Exceptional, (52)
"We had such a lovely two days celebrating birthdays. The house is beautiful and so are the grounds. We had everything we needed. I have given a good for the area because we could not use the pool. "
Spacious period property on historic, private estate with seasonal, outdoor pool
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool
Interior

SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool

10.0 out of 10, Exceptional, (21)
"Excellent property in a beautiful & peaceful setting. Garden House was very well equipped & very comfortable. Hosts helpful & pleasant . We enjoyed our stay there. "
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool
Host Stay Fieldview Lodge Ashdown Retreat
House | 2 bedrooms

Host Stay Fieldview Lodge Ashdown Retreat

2.0 star property
Host Stay Fieldview Lodge Ashdown Retreat
No. 10 West End Osmotherley
Exterior detail

No. 10 West End Osmotherley

9.6 out of 10, Exceptional, (41)
"Had a very enjoyanle stay."
No. 10 West End Osmotherley
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
Fridge, microwave, oven, stovetop

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

10.0 out of 10, Exceptional, (72)
"We loved the house, clean, spacious and well equipped. Also loved the location, Helmsley is a lovely town and there are many attractions nearby."
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
Host Stay Linden Lodge Ashdown Retreat
House | Desk

Host Stay Linden Lodge Ashdown Retreat

2.0 star property
The price is £256
includes taxes & fees
7 Aug - 8 Aug
Host Stay Linden Lodge Ashdown Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Helmsley Hotel Reviews

The Old Lodge

The Old Lodge

10/10 Excellent
"Staff were friendly and bubbly. All around great service "
abdulhaq 2-night trip
Posted 18 hours ago
The Old Lodge