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Our top choices for Helmsley vacation 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 ¥73,770
¥80,119 total
includes taxes & fees
Nov 12 - Nov 13
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 ¥388,140
¥388,140 total
includes taxes & fees
Nov 10 - Nov 11
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 ¥10,500
¥24,028 total
includes taxes & fees
Dec 6 - Dec 7
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 ¥32,166
¥85,705 total
includes taxes & fees
Nov 10 - Nov 11
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 ¥87,694
¥105,233 total
includes taxes & fees
Nov 30 - Dec 1
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 ¥11,463
¥13,756 total
includes taxes & fees
Nov 11 - Nov 12
Vas's York House

8. Home and Away

Home and Away
Eaglescliffe
The price is ¥22,855
¥24,971 total
includes taxes & fees
Nov 10 - Nov 11
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 ¥75,759
¥94,805 total
includes taxes & fees
Nov 10 - Nov 11
Host & Stay | Finch House

10. Roman Cottage - Hot Tub, sleeps 12

Roman Cottage - Hot Tub, sleeps 12
York
The price is ¥143,265
¥151,730 total
includes taxes & fees
Nov 11 - Nov 12
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 ¥13,747
¥26,444 total
includes taxes & fees
Nov 30 - Dec 1
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 ¥31,806
¥34,557 total
includes taxes & fees
Nov 24 - Nov 25
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 ¥21,162
¥23,278 total
includes taxes & fees
Nov 10 - Nov 11
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 ¥8,841
¥18,228 total
includes taxes & fees
Dec 6 - Dec 7
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 ¥16,951
¥24,146 total
includes taxes & fees
Nov 10 - Nov 11
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
The price is ¥21,902
¥34,747 total
includes taxes & fees
Nov 11 - Nov 12
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 ¥21,697
¥41,801 total
includes taxes & fees
Nov 11 - Nov 12
The Hill - 3-Bed Home with Garden and Parking

18. Portman House

Portman House
Middlesbrough
The price is ¥13,332
¥19,681 total
includes taxes & fees
Dec 7 - Dec 8
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 ¥15,236
¥17,352 total
includes taxes & fees
Nov 15 - Nov 16
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 ¥32,851
¥39,421 total
includes taxes & fees
Nov 15 - Nov 16
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.
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Top Helmsley Hotel Reviews

Find out more about Helmsley

Helmsley Vacation Homes information

Number of reviews
96
Accommodation
827 Vacation Homes
Lowest Price
¥13,756
Highest Price
¥388,140