Photo by Paul Lakin

Search Helmsley Cottages

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Helmsley cottages

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
$507 nightly
The price is $609
Dec 5 - Dec 6
Total with taxes and fees
Ivy Cottage

2. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
$667 nightly
The price is $667
Nov 25 - Nov 26
Total with taxes and fees
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
$872 nightly
The price is $872
Nov 18 - Nov 19
Total with taxes and fees
Eighteen Pottergate - Beautiful cottage with garden central location

4. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Hyland Cottage - sleeps 6 guests in 3 bedrooms
Helmsley
$1,451 nightly
The price is $1,451
Nov 18 - Nov 19
Total with taxes and fees
Hyland Cottage - sleeps 6 guests in 3 bedrooms

5. 29 Bondgate

29 Bondgate
3.5 star property
York
$613 nightly
The price is $736
Nov 18 - Nov 19
Total with taxes and fees
29 Bondgate

6. Cliff House

Cliff House
3.5 star property
York
$628 nightly
The price is $754
Nov 18 - Nov 19
Total with taxes and fees
Cliff House

7. Holly Cottage

Holly Cottage
3.0 star property
York
$820 nightly
The price is $984
Nov 13 - Nov 14
Total with taxes and fees
Holly Cottage

8. Keldholme Cottages 2 - UK11488

Keldholme Cottages 2 - UK11488
Keldholme, near Kirkbymoorside
10.0 out of 10, Exceptional, (9 reviews)
"Lovely and cosy cottage. Ideal for holiday stay. We thoroughly enjoyed our stay there."
United States
Kevin Jones
$324 nightly
The price is $324
Dec 8 - Dec 9
Total with taxes and fees
Keldholme Cottages 2 - UK11488

9. 1 bedroom accommodation in Slingsby, near Malton

1 bedroom accommodation in Slingsby, near Malton
Slingsby, near Malton
10.0 out of 10, Exceptional, (9 reviews)
"Lovely cottage. Welcoming and homely with everything provided that we needed. Good place for a relax and good walking for the dog."
United States
Carol Horne
$463 nightly
The price is $463
Nov 13 - Nov 14
Total with taxes and fees
1 bedroom accommodation in Slingsby, near Malton

10. Keldholme Cottage 1 - UK10992

Keldholme Cottage 1 - UK10992
Keldholme, near Kirkbymoorside
9.8 out of 10, Exceptional, (10 reviews)
"Excellent for get away from it all beautiful countryside and walks."
United States
John Kelly
$271 nightly
The price is $271
Nov 18 - Nov 19
Total with taxes and fees
Keldholme Cottage 1 - UK10992

11. Heather Cottage - a beautiful cosy cottage

Heather Cottage - a beautiful cosy cottage
Snainton
9.0 out of 10, Wonderful, (2 reviews)
"Clean, organised flat in a lovely area. The hosts communication was great throughout, and there was a great guest book containing recommendations for the local area."
United Kingdom
Luigi
$132 nightly
The price is $132
Nov 11 - Nov 12
Total with taxes and fees
Heather Cottage - a beautiful cosy cottage

12. Hungate Garden Cottage

Hungate Garden Cottage
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"Great accommodation as advertised. "
United States
simon g.
$1,263 nightly
The price is $1,263
Nov 26 - Nov 27
Total with taxes and fees
Hungate Garden Cottage

13. 2 bedroom accommodation in Pickering

2 bedroom accommodation in Pickering
Pickering
10.0 out of 10, Exceptional, (4 reviews)
"Surprisingly roomy cottage, ideal for solo travellers or families up to four. Great location for exploring wonderful North Yorkshire, lots to see and do. Cottage is cosy with beautiful finishes. I can highly recommend 4 Smiddy Hill for a short break or longer stay."
United States
Jean L.
$463 nightly
The price is $463
Nov 23 - Nov 24
Total with taxes and fees
2 bedroom accommodation in Pickering

14. 4 bedroom accommodation in Pickering

4 bedroom accommodation in Pickering
Pickering
10.0 out of 10, Exceptional, (6 reviews)
"Fabulous location in Pickering and yet so peaceful. Beautifully maintained property and gardens. Warm and cozy with everything that you need for cooking etc. Fabulous places to visit within 30 mins - 1 hour drive - spoilt for choice. Review independently collected and verified by Reevoo"
United States
Maria
$824 nightly
The price is $824
Nov 26 - Nov 27
Total with taxes and fees
4 bedroom accommodation in Pickering

15. 2 bedroom accommodation in Pickering

2 bedroom accommodation in Pickering
Pickering
9.2 out of 10, Wonderful, (12 reviews)
"The location and the fact that it included parking were great. The cottage was warm, comfortable and well thought out."
United States
Peter J.
$298 nightly
The price is $298
Dec 10 - Dec 11
Total with taxes and fees
2 bedroom accommodation in Pickering

16. Stoney Nook Cottage

Stoney Nook Cottage
Guisborough
9.2 out of 10, Wonderful, (5 reviews)
"Beautifully renovated cottage with comfortable bed and modern washroom. Conveniently located for exploring Guisborough and helpful guidebook with suggestions for the kids and adults. The grocery store is a 5-minute block away also. Andy was very helpful and easy to communicate with."
Canada
Shelley & J.
$100 nightly
The price is $100
Nov 23 - Nov 24
Total with taxes and fees
Stoney Nook Cottage

17. Lilac Cottage

Lilac Cottage
3.0 star property
York
9.0 out of 10, Wonderful, (2 reviews)
"Lovely cottage in a quiet village."
United States
Kevin
$435 nightly
The price is $522
Nov 15 - Nov 16
Total with taxes and fees
Lilac Cottage

18. Cosy, 2 Bedroom Cottage in Guisborough Town Centre

Cosy, 2 Bedroom Cottage in Guisborough Town Centre
North Yorkshire
10.0 out of 10, Exceptional, (2 reviews)
"It’s well situated and a nice place to stay. "
United States
jane
$100 nightly
The price is $100
Nov 23 - Nov 24
Total with taxes and fees
Cosy, 2 Bedroom Cottage in Guisborough Town Centre

19. 3 bedroom accommodation in Pickering

3 bedroom accommodation in Pickering
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"Hungate cottages are perfectly placed near to Pickering town centre. Beautiful complex of converted barns and cottages. Our cottage was spacious, well equipped and very comfortable. We had a great week, thank you."
United Kingdom
Elizabeth H.
$658 nightly
The price is $658
Nov 26 - Nov 27
Total with taxes and fees
3 bedroom accommodation in Pickering

20. Lovebird Lodge - UK51939

Lovebird Lodge - UK51939
Yarm
$406 nightly
The price is $406
Nov 18 - Nov 19
Total with taxes and fees
Lovebird Lodge - UK51939
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