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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$715 nightly
The price is $715
Nov 3 - Nov 4
Total with taxes and fees
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A stone house with a tiled roof, a front porch, and a small garden.

2. Ivy Cottage

Ivy Cottage
4.0 star property
York
Ivy Cottage
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
$915 nightly
The price is $915
Nov 7 - Nov 8
Total with taxes and fees
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
$1,575 nightly
The price is $1,575
Nov 15 - Nov 16
Total with taxes and fees
Hyland 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.

5. Cliff House

Cliff House
3.5 star property
York
$573 nightly
The price is $687
Nov 18 - Nov 19
Total with taxes and fees
Cliff House
A stone building with a gabled roof, a green door, and a window with white shutters.

6. 29 Bondgate

29 Bondgate
3.5 star property
York
$559 nightly
The price is $671
Nov 3 - Nov 4
Total with taxes and fees
29 Bondgate
A traditional thatched-roof cottage with a green door, white walls, and a small garden with pink flowers.

7. Holly Cottage

Holly Cottage
3.0 star property
York
$748 nightly
The price is $898
Nov 3 - Nov 4
Total with taxes and fees
Holly Cottage
A stone house with a tiled roof, surrounded by a well-maintained lawn and dense greenery.

8. 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 8 - Nov 9
Total with taxes and fees
Keldholme Cottage 1 - UK10992
A stone house with a tiled roof, a wooden door, and a garden area with a hose and plants.

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
$464 nightly
The price is $464
Nov 3 - Nov 4
Total with taxes and fees
1 bedroom accommodation in Slingsby, near Malton
A stone house with a tiled roof, multiple windows, and a well-maintained lawn.

10. 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
$325 nightly
The price is $325
Nov 11 - Nov 12
Total with taxes and fees
Keldholme Cottages 2 - UK11488
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

11. Heather Cottage - a beautiful cosy cottage

Heather Cottage - a beautiful cosy cottage
Snainton
10.0 out of 10, Exceptional, (1 review)
"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
$147 nightly
The price is $147
Nov 15 - Nov 16
Total with taxes and fees
Heather Cottage - a beautiful cosy cottage
A stone building with a white door, windows, and outdoor seating.

12. Between Coast & Moors | Pickering 2BR | Sleeps 4

Between Coast & Moors | Pickering 2BR | Sleeps 4
Pickering
8.0 out of 10, Very good, (5 reviews)
"We were so pleased with this cottage. It was clean, modern and very well equipped. Would certainly recommend it to my friends. "
United Kingdom
Brenda
$285 nightly
The price is $285
Oct 28 - Oct 29
Total with taxes and fees
Between Coast & Moors | Pickering 2BR | Sleeps 4
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.
$464 nightly
The price is $464
Nov 8 - Nov 9
Total with taxes and fees
2 bedroom accommodation in Pickering
A cozy living room with a sofa, a dining table, and a kitchen in the background.

14. Hungate Garden Cottage

Hungate Garden Cottage
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"Great accommodation as advertised. "
United States
simon g.
$1,265 nightly
The price is $1,265
Nov 12 - Nov 13
Total with taxes and fees
Hungate Garden Cottage
A stone building with a tiled roof, multiple windows, and a bench outside.

15. 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.
$659 nightly
The price is $659
Nov 12 - Nov 13
Total with taxes and fees
3 bedroom accommodation in Pickering
A two-story brick house with a bay window, a black front door, and satellite dishes on the roof.

16. 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
$118 nightly
The price is $118
Oct 26 - Oct 27
Total with taxes and fees
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.

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
$397 nightly
The price is $476
Nov 14 - Nov 15
Total with taxes and fees
Lilac Cottage
A stone building with a bay window, a door, and a small shop sign.

18. 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.
$118 nightly
The price is $118
Oct 25 - Oct 26
Total with taxes and fees
Stoney Nook Cottage
A backyard with a hot tub, a barbecue grill, wicker furniture, and a stone wall.

19. Dalby Cottage | sleeps 6 - Hot Tub, Dog Friendly - 5* Gold

Dalby Cottage | sleeps 6 - Hot Tub, Dog Friendly - 5* Gold
Pickering
10.0 out of 10, Exceptional, (4 reviews)
"Great place and especially good if you have dogs"
United States
Peter W.
$900 nightly
The price is $900
Oct 30 - Oct 31
Total with taxes and fees
Dalby Cottage | sleeps 6 - Hot Tub, Dog Friendly - 5* Gold
A rustic brick building with a reception sign, a parked vehicle, and outdoor seating area.

20. The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave

The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
High Leven
8.0 out of 10, Very good, (14 reviews)
"Clean, well presented "
United Kingdom
Martin E.
$135 nightly
The price is $135
Nov 3 - Nov 4
Total with taxes and fees
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
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

The Minster Hotel York

The Minster Hotel York

8/10 Good
"Location excellent. Car park incredibly useful. Very helpful staff and freshly cooked breakfast was lovely every morning."
Karen 3-night trip
Posted 21 hours ago
The Minster Hotel York

Find out more about Helmsley

Helmsley Cottages information

Number of reviews
75
Accommodation
1671 Cottages
Lowest Price
$118
Highest Price
$1,575