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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 1,709
AED 1,856 total
includes taxes & fees
11 Dec - 12 Dec

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 9,055
AED 9,055 total
includes taxes & fees
12 Nov - 13 Nov

4. 2-bed House Sleeps 4 - Private Garden - Pets Ok
2-bed House Sleeps 4 - Private Garden - Pets OkMiddlesbrough
The price is AED 239
AED 551 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 750
AED 1,999 total
includes taxes & fees
9 Dec - 10 Dec

6. 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 593 total
includes taxes & fees
12 Nov - 13 Nov

7. Home and Away
Home and AwayEaglescliffe
The price is AED 529
AED 579 total
includes taxes & fees
12 Nov - 13 Nov

8. Manor Cottage
Manor CottagePickering
The price is AED 2,032
AED 2,438 total
includes taxes & fees
30 Nov - 1 Dec

9. 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

10. 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
7 Dec - 8 Dec

11. Blossom Cottage, sleeps 5
Blossom Cottage, sleeps 5York
The price is AED 1,407
AED 1,604 total
includes taxes & fees
12 Nov - 13 Nov

12. Host & Stay | Finch House
Host & Stay | Finch HouseStokesley
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 1,755
AED 2,196 total
includes taxes & fees
12 Nov - 13 Nov

13. 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 806 total
includes taxes & fees
24 Nov - 25 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. The Bungalow, Lingdale
The Bungalow, LingdaleLingdale
6.0 out of 10, (2 reviews)
The price is AED 490
AED 539 total
includes taxes & fees
12 Nov - 13 Nov

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

17. 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 353
AED 402 total
includes taxes & fees
23 Nov - 24 Nov

18. 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 968 total
includes taxes & fees
19 Nov - 20 Nov

20. Modern Stockton Retreat Sleeps 6 by Stay With Us
Modern Stockton Retreat Sleeps 6 by Stay With UsStockton-on-Tees
The price is AED 676
AED 1,536 total
includes taxes & fees
13 Nov - 14 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

































































