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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 2Helmsley
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,710
AED 1,857 total
includes taxes & fees
12 Nov - 13 Nov

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

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 AwardPickering
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 8,996
AED 8,996 total
includes taxes & fees
11 Nov - 12 Nov

4. 2-bed House Sleeps 4 - Private Garden - Pets Ok
2-bed House Sleeps 4 - Private Garden - Pets OkMiddlesbrough
The price is AED 243
AED 557 total
includes taxes & fees
6 Dec - 7 Dec

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 MoorsGlaisdale
10.0 out of 10, Exceptional, (44 reviews)
The price is AED 745
AED 1,986 total
includes taxes & fees
11 Nov - 12 Nov

6. Manor Cottage
Manor CottagePickering
The price is AED 2,032
AED 2,439 total
includes taxes & fees
30 Nov - 1 Dec

7. Vas's York House
Vas's York HouseClifton
7.6 out of 10, Good, (7 reviews)
The price is AED 266
AED 319 total
includes taxes & fees
11 Nov - 12 Nov

8. Home and Away
Home and AwayEaglescliffe
The price is AED 530
AED 579 total
includes taxes & fees
12 Nov - 13 Nov

9. Host & Stay | Finch House
Host & Stay | Finch HouseStokesley
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 1,767
AED 2,212 total
includes taxes & fees
11 Nov - 12 Nov

10. Roman Cottage - Hot Tub, sleeps 12
Roman Cottage - Hot Tub, sleeps 12York
The price is AED 3,322
AED 3,520 total
includes taxes & fees
12 Nov - 13 Nov

11. The Great Ayton Hideaway
The Great Ayton HideawayGreat Ayton
8.0 out of 10, Very good, (1 review)
The price is AED 321
AED 617 total
includes taxes & fees
30 Nov - 1 Dec

12. Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work StaysRainton
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 742
AED 772 total
includes taxes & fees
25 Nov - 26 Nov

13. The Bungalow, Lingdale
The Bungalow, LingdaleLingdale
6.0 out of 10, (2 reviews)
The price is AED 494
AED 543 total
includes taxes & fees
11 Nov - 12 Nov

14. 1 Bed Flat Sleeps 2 - Pets Welcome - Tv & Wifi
1 Bed Flat Sleeps 2 - Pets Welcome - Tv & WifiMiddlesbrough
The price is AED 203
AED 420 total
includes taxes & fees
6 Dec - 7 Dec

15. Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFiHolgate
8.6 out of 10, Excellent, (17 reviews)
The price is AED 395
AED 563 total
includes taxes & fees
11 Nov - 12 Nov

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)

17. The Hill - 3-Bed Home with Garden and Parking
The Hill - 3-Bed Home with Garden and ParkingStockton-on-Tees
The price is AED 503
AED 969 total
includes taxes & fees
11 Nov - 12 Nov

18. Portman House
Portman HouseMiddlesbrough
The price is AED 309
AED 456 total
includes taxes & fees
7 Dec - 8 Dec

19. 2 Bedroom House with Garden next to the River Tees
2 Bedroom House with Garden next to the River TeesStockton on Tees
10.0 out of 10, Exceptional, (4 reviews)
The price is AED 355
AED 405 total
includes taxes & fees
15 Nov - 16 Nov

20. 18 Horner Street York
18 Horner Street YorkClifton
9.2 out of 10, Wonderful, (9 reviews)
The price is AED 766
AED 920 total
includes taxes & fees
15 Nov - 16 Nov
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.

Photo by Paul Lakin
Open Photo by Paul Lakin
































































