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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Helmsley cottages

A stone house with a red-tiled roof, a blue door, and a narrow stone pathway leading to the entrance.

1. Cliff House

Cliff House
3.5 star property
York
The price is AU$980
includes taxes & fees
7 Sept - 8 Sept
Cliff House

2. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
The price is AU$1,301
includes taxes & fees
11 Sept - 12 Sept
Eighteen Pottergate - Beautiful cottage with garden central location
A stone building with a gabled roof, a green door, and a window with white shutters.

3. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is AU$957
includes taxes & fees
12 Sept - 13 Sept
29 Bondgate
A stone house with a tiled roof, a front porch, and a small garden.

4. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is AU$1,317
includes taxes & fees
12 Sept - 13 Sept
Ivy Cottage
A two-story stone house with a red-tiled roof, a wooden fence, and a paved driveway.

5. Lilac Cottage

Lilac Cottage
3.0 star property
York
10.0 out of 10, Exceptional, (1 review)
"Lovely cottage in a quiet village."
United States
Kevin
The price is AU$554
includes taxes & fees
18 Sept - 19 Sept
Lilac Cottage
A stone-built two-story house with a tiled roof, multiple windows, and doors.

6. 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 AU$501
includes taxes & fees
31 Aug - 1 Sept
Keldholme Cottage 1 - UK10992
A stone house with a tiled roof, a wooden door, and a garden area with a hose and plants.

7. 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)
"Fantastic cosy cottage well equipped and lovely welcome pack provided.Stayed at a few cottages in Slingsby and this one is by far the best.Lovely quaint village with amazing pub only 100 meters away.Highly recommended and I will surely return again soon"
United States
Jonathan Stewart
The price is AU$661
includes taxes & fees
24 Sept - 25 Sept
1 bedroom accommodation in Slingsby, near Malton
A stone house with a tiled roof, multiple windows, and a well-maintained lawn.

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
The price is AU$596
includes taxes & fees
6 Sept - 7 Sept
Keldholme Cottages 2 - UK11488
A stone house with a sloped roof, two windows, and a well-maintained lawn.

9. Willow Cottage 4 bedroom Cosy stopover, dogs welcome

Willow Cottage 4 bedroom Cosy stopover, dogs welcome
Thornton-le-Beans
10.0 out of 10, Exceptional, (5 reviews)
"Immaculate and cosy home. Quiet village, friendly pub, ideal jumping-off point for exploring the area."
United Kingdom
James C.
The price is AU$443
includes taxes & fees
1 Sept - 2 Sept
Willow Cottage 4 bedroom Cosy stopover, dogs welcome
A stone building with a white door, windows, and outdoor seating.

10. 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
The price is AU$439
includes taxes & fees
12 Sept - 13 Sept
Between Coast & Moors • Pickering 2BR • Sleeps 4
A stone building with three windows and a sign reading "Little Fyther."

11. Little Pythorn - UK45253

Little Pythorn - UK45253
Westerdale, near Castleton
9.8 out of 10, Exceptional, (6 reviews)
"A wonderful stay in a beautiful cottage. A really good relaxing break. Some excellent places to eat but remember you’re in the North YorkshireMoors. Lots of lovely walks around and places to visit.We will be back!"
United States
Kath W.
The price is AU$482
includes taxes & fees
24 Sept - 25 Sept
Little Pythorn - UK45253
A traditional brick building with a reception area, a parked vehicle, and outdoor seating.

12. 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)
"Angie is a lovely warm welcoming lady , nothing was a bother , only staid one night as was having a meal in the Fox Covert next door which is really great place , The cottage was a propped cottage feel , and could sleep upto 6 but was only the two of us , proper kitchen and shower n toilet was compact but everything you needed , lovely place to stay and will be back , also location is good for all local amenities and local attractions, Thank you "
United States
Martin B.
The price is AU$176
includes taxes & fees
3 Sept - 4 Sept
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

13. Heather Cottage - a beautiful cosy cottage

Heather Cottage - a beautiful cosy cottage
Snainton
The price is AU$212
includes taxes & fees
22 Sept - 23 Sept
Heather Cottage - a beautiful cosy cottage
A stone building with a bay window, a door, and a small shop sign.

14. 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 AU$171
includes taxes & fees
7 Sept - 8 Sept
Stoney Nook Cottage
A brick building with multiple windows, a door, and a gravel driveway.

15. Tuft House

Tuft House
2.0 star property
York
The price is AU$4,687
includes taxes & fees
31 Aug - 1 Sept
Tuft House
A traditional house with a tiled roof, a well-maintained lawn, and a stone wall.

16. 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 AU$501
includes taxes & fees
4 Sept - 5 Sept
2 bedroom accommodation in Pickering
A brick building with a tiled roof, outdoor seating, and potted plants.

17. The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite

The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite
High Leven
7.8 out of 10, Good, (8 reviews)
"Quirky. Most comfortable bed we've ever slept in."
United Kingdom
Leigh
The price is AU$397
includes taxes & fees
4 Sept - 5 Sept
The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite
A modern kitchen with dark cabinets, a microwave, a sink, and a window above the sink.

18. Little Esklets - UK45252

Little Esklets - UK45252
Westerdale, near Castleton
10.0 out of 10, Exceptional, (2 reviews)
"This is a little gem hidden away in the Yorkshire moors. In a fabulous location with stunning views of the surrounding fields and moors.The cottage has everything you would need and more."
United States
Maria Godby
The price is AU$556
includes taxes & fees
9 Sept - 10 Sept
Little Esklets - UK45252

19. Dove Lodge - UK51935

Dove Lodge - UK51935
Yarm
The price is AU$579
includes taxes & fees
7 Sept - 8 Sept
Dove Lodge - UK51935
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
"Excellent family-run hotel; fantastic location right near the Minster and in the heart of the Old Town. Stumbling distance from every pub in town Staff were very nice throughout - in fact I wondered if they were for real - they were. Our rooms were brand new. No AC but that's a British thing, I think. Plumbing worked though! The fried breakfasts are huge but there are plenty of other healthy options. The breakfast room itself is in the older part and needs a little TLC but that is a minor observation. A perfect hotel for families and couples.PS. I often felt I was in the middle of an Alan Bennett play because the place felt so nostalgic, in a good way."
richard gwyn 2-night trip
Posted 2 hours ago
The Minster Hotel York

Find out more about Helmsley

Helmsley Cottages information

Number of reviews
86
Accommodation
1669 Cottages
Lowest Price
AU$171
Highest Price
AU$4,687