Photo by Paul Lakin

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Our top choices for Helmsley holiday homes

1. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
10.0 out of 10, Exceptional, (1 review)
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is £373
includes taxes & fees
12 Nov - 13 Nov
Beautiful stone cottage in the heart of Helmsley - sleeps 2

2. WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms

WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms
KIRBYMOORSIDE
WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms

3. The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award

The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Pickering
10.0 out of 10, Exceptional, (3 reviews)
"Eight friends (5 of whom were at uni together in the 70s) meet every year. Yorkshire was this year’s choice. We couldn’t have stayed in a better location. We loved everything: the house; the swim spa; the area; the weather. We would love to come back. Thank you!"
United Kingdom
Deborah H.
The price is £1,834
includes taxes & fees
11 Nov - 12 Nov
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award

4. 2-bed House Sleeps 4 - Private Garden - Pets Ok

2-bed House Sleeps 4 - Private Garden - Pets Ok
3.0 star property
Middlesbrough
The price is £114
includes taxes & fees
6 Dec - 7 Dec
2-bed House Sleeps 4 - Private Garden - Pets Ok

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

Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Glaisdale
10.0 out of 10, Exceptional, (44 reviews)
"The property was excellent, beautiful throughout. We enjoyed our stay and the hosts were very welcoming and friendly. We would highly recommend "
United Kingdom
Catherine C.
The price is £408
includes taxes & fees
11 Nov - 12 Nov
Luxury retreat for 2 couples/ family in spectacular location in North York Moors

6. Manor Cottage

Manor Cottage
3.0 star property
Pickering
The price is £497
includes taxes & fees
30 Nov - 1 Dec
Manor Cottage

7. Vas's York House

Vas's York House
2.0 star property
Clifton
7.6 out of 10, Good, (7 reviews)
"Great location (less than 10 minutes from the train station and old town centre). The hosts were kind and overall it was a sufficiently pleasant experience."
United Kingdom
Emilie
The price is £60
includes taxes & fees
11 Nov - 12 Nov
Vas's York House

8. Home and Away

Home and Away
Eaglescliffe
The price is £120
includes taxes & fees
11 Nov - 12 Nov
Home and Away

9. Host & Stay | Finch House

Host & Stay | Finch House
Stokesley
9.0 out of 10, Wonderful, (2 reviews)
"A perfect stay in a beautiful property. I always say you get what you pay for, so while it seemed expensive when I booked it, it was so worth the money. Everything was spot on, the furnishings were sumptuous, furniture and beds were top quality, bedrooms and bathrooms were luxurious. Host was great and left a lovely welcome hamper with wine, chocolate etc. All in all, I couldn't fault Finch House"
United States
jeanette w.
The price is £448
includes taxes & fees
11 Nov - 12 Nov
Host & Stay | Finch House

10. Roman Cottage - Hot Tub, sleeps 12

Roman Cottage - Hot Tub, sleeps 12
York
The price is £713
includes taxes & fees
13 Nov - 14 Nov
Roman Cottage - Hot Tub, sleeps 12

11. The Great Ayton Hideaway

The Great Ayton Hideaway
Great Ayton
8.0 out of 10, Very good, (1 review)
"Did what it said on the tin"
United Kingdom
Nick L.
The price is £125
includes taxes & fees
30 Nov - 1 Dec
The Great Ayton Hideaway

12. Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays

Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
Rainton
9.0 out of 10, Wonderful, (2 reviews)
"Family friendly , just as described on the booking, very clean and spacious we had no complaints, we paid 10 for earlier check in which was fantastic thank you!"
United States
Emily B.
The price is £162
includes taxes & fees
24 Nov - 25 Nov
Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays

13. The Bungalow, Lingdale

The Bungalow, Lingdale
Lingdale
6.0 out of 10, (2 reviews)
"Does the job if you just need a place to sleep in the area but it needs some TLC and the garden is over grown, not sure if the heating is working. I'd hace still rated it as average as lomg as your not taking the family on holiday but communication feom the host was dreadful. I shluld have tp asl a half dozen times for access info, its not necessary and it adds to the stress. No one wants to make a three hour drive without knowing they will be able to get in when they get there "
United Kingdom
Michael
The price is £112
includes taxes & fees
11 Nov - 12 Nov
The Bungalow, Lingdale

14. 1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi

1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi
3.0 star property
Middlesbrough
The price is £86
includes taxes & fees
6 Dec - 7 Dec
1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi

15. Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Holgate
8.6 out of 10, Excellent, (17 reviews)
"Love the place."
United States
Lee Y.
The price is £115
includes taxes & fees
11 Nov - 12 Nov
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

16. Garden Gazebo. Free Parking. 20 mins walk to City and train station.

Garden Gazebo. Free Parking. 20 mins walk to City and train station.
Holgate
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely brulliant property.. a home away from home"
United Kingdom
John
Garden Gazebo. Free Parking. 20 mins walk to City and train station.

17. The Hill - 3-Bed Home with Garden and Parking

The Hill - 3-Bed Home with Garden and Parking
Stockton-on-Tees
The price is £198
includes taxes & fees
12 Nov - 13 Nov
The Hill - 3-Bed Home with Garden and Parking

18. Portman House

Portman House
Middlesbrough
The price is £95
includes taxes & fees
7 Dec - 8 Dec
Portman House

19. 2 Bedroom House with Garden next to the River Tees

2 Bedroom House with Garden next to the River Tees
Stockton on Tees
10.0 out of 10, Exceptional, (4 reviews)
"Good location, host was very responsive, property had everything we needed. Good check-in/out process "
United Kingdom
David R.
The price is £84
includes taxes & fees
15 Nov - 16 Nov
2 Bedroom House with Garden next to the River Tees

20. 18 Horner Street York

18 Horner Street York
3.0 star property
Clifton
9.2 out of 10, Wonderful, (9 reviews)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
Australia
Christina
The price is £209
includes taxes & fees
15 Nov - 16 Nov
18 Horner Street York
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.

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.

A historic castle ruin with two towers on a grassy hill.
Photo by Paul Lakin
Open Photo by Paul Lakin

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