A medieval castle surrounded by a lush green landscape and a small village in the background.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Helmsley cottages

A two-story brick house with a tiled roof, a front garage, and a well-maintained lawn.

1. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A stone house with a red-tiled roof, a blue door, and a narrow stone pathway leading to the entrance.

2. Cliff House

Cliff House
3.5 star property
York
The price is €610
includes taxes & fees
5 Nov - 6 Nov
Cliff House
A stone house with a tiled roof, a paved driveway, and a small garden area.

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
Eighteen Pottergate - Beautiful cottage with garden central location
A stone house with a tiled roof, a gated driveway, and a parked car.

4. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Hyland Cottage - sleeps 6 guests in 3 bedrooms
Helmsley
Hyland Cottage - sleeps 6 guests in 3 bedrooms
A stone building with a gabled roof, a green door, and a window with white shutters.

5. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is €595
includes taxes & fees
9 Nov - 10 Nov
29 Bondgate
A traditional thatched-roof cottage with a green door, white walls, and a small garden with pink flowers.

6. Holly Cottage

Holly Cottage
3.0 star property
York
The price is €884
includes taxes & fees
8 Nov - 9 Nov
Holly Cottage
A stone-built two-story house with a tiled roof, multiple windows, and doors.

7. 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
The price is €244
includes taxes & fees
8 Nov - 9 Nov
Keldholme Cottage 1 - UK10992
A stone house with a tiled roof, a wooden door, and a garden area with a hose and plants.

8. 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
The price is €416
includes taxes & fees
2 Nov - 3 Nov
1 bedroom accommodation in Slingsby, near Malton
A two-story stone house with a red-tiled roof, multiple windows, and doors.

9. 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
The price is €292
includes taxes & fees
11 Nov - 12 Nov
Keldholme Cottages 2 - UK11488
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

10. 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
The price is €138
includes taxes & fees
5 Nov - 6 Nov
Heather Cottage - a beautiful cosy cottage
A traditional house with a tiled roof, a well-maintained lawn, and a stone wall.

11. 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.
The price is €268
includes taxes & fees
12 Nov - 13 Nov
2 bedroom accommodation in Pickering
A cozy living room with a sofa, a dining table, and a kitchen in the background.

12. Hungate Garden Cottage

Hungate Garden Cottage
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"Great accommodation as advertised. "
United States
simon g.
Hungate Garden Cottage
A brick building with multiple windows, a small garden area with potted plants, and a flag on the roof.

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.
2 bedroom accommodation in Pickering
A stone building with a tiled roof, multiple windows, and a bench outside.

14. 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.
The price is €592
includes taxes & fees
12 Nov - 13 Nov
3 bedroom accommodation in Pickering
A two-story brick house with a bay window, a black front door, and satellite dishes on the roof.

15. 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
The price is €111
includes taxes & fees
23 Nov - 24 Nov
Cosy, 2 Bedroom Cottage in Guisborough Town Centre
A two-story stone house with a red-tiled roof, a wooden fence, and a paved driveway.

16. 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
The price is €422
includes taxes & fees
14 Nov - 15 Nov
Lilac Cottage
A stone building with a bay window, a door, and a small shop sign.

17. 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.
The price is €111
includes taxes & fees
15 Nov - 16 Nov
Stoney Nook Cottage
Exterior | Lovebird Lodge - Holmewood Lakes, Yarm

18. Lovebird Lodge - UK51939

Lovebird Lodge - UK51939
Yarm
The price is €365
includes taxes & fees
2 Nov - 3 Nov
Lovebird Lodge - UK51939
Exterior | Kingfisher Lodge - Holmewood Lakes, Yarm

19. Kingfisher Lodge - UK51933

Kingfisher Lodge - UK51933
Yarm
The price is €365
includes taxes & fees
2 Nov - 3 Nov
Kingfisher Lodge - UK51933
A green building with large windows, a sliding door, and a wicker sofa with cushions.

20. 2 bedroom accommodation in East Heslerton

2 bedroom accommodation in East Heslerton
East Heslerton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay very clean and modern.Hot tub was great after a day of walking."
United States
Jason Smith
2 bedroom accommodation in East Heslerton
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

Burn Hall Hotel

Burn Hall Hotel

10/10 Excellent
"Great hotel we stayed there at least 3 times, great value hotel, only a bit further out but not much an issue as you need to drive there to get anyway. I would definitely recommend it."
Ilhan 1-night trip
Posted 3 hours ago
Burn Hall Hotel

Find out more about Helmsley

Helmsley Cottages information

Number of reviews
73
Accommodation
1676 Cottages
Lowest Price
€111
Highest Price
€884