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

Search Helmsley Cottage Rentals from CA $164

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Helmsley cottages

A stone house with a tiled roof, a front porch, and a small garden.

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is CA $647
CA $776 total
includes taxes & fees
Oct 3 - Oct 4
Ivy Cottage
A two-story brick house with a tiled roof, a front garage, and a well-maintained lawn.

2. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
The price is CA $981
CA $1,121 total
includes taxes & fees
Sep 29 - Sep 30
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
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
The price is CA $1,178
CA $1,279 total
includes taxes & fees
Sep 29 - Sep 30
Eighteen Pottergate - Beautiful cottage with garden central location
A stone house with a red-tiled roof, a blue door, and a narrow stone pathway leading to the entrance.

4. Cliff House

Cliff House
3.5 star property
York
The price is CA $801
CA $961 total
includes taxes & fees
Oct 6 - Oct 7
Cliff House
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 CA $783
CA $940 total
includes taxes & fees
Oct 9 - Oct 10
29 Bondgate
A two-story stone house with a red-tiled roof, a wooden fence, and a paved driveway.

6. 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 CA $453
CA $543 total
includes taxes & fees
Oct 2 - Oct 3
Lilac Cottage
A stone house with a tiled roof, surrounded by a well-maintained lawn and dense greenery.

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 CA $444
CA $444 total
includes taxes & fees
Sep 27 - Sep 28
Keldholme Cottage 1 - UK10992
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

8. 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
The price is CA $146
CA $212 total
includes taxes & fees
Sep 28 - Sep 29
Heather Cottage - a beautiful cosy cottage
A two-story brick house with a bay window, a black front door, and satellite dishes on the roof.

9. 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 CA $135
CA $164 total
includes taxes & fees
Oct 4 - Oct 5
Cosy, 2 Bedroom Cottage in Guisborough Town Centre
A stone house with a tiled roof, a wooden door, and a garden area with a hose and plants.

10. 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 CA $694
CA $694 total
includes taxes & fees
Oct 9 - Oct 10
1 bedroom accommodation in Slingsby, near Malton
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, (7 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 CA $474
CA $474 total
includes taxes & fees
Sep 27 - Sep 28
Little Pythorn - UK45253
A stone house with a tiled roof, multiple windows, and a well-maintained lawn.

12. 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 CA $547
CA $547 total
includes taxes & fees
Oct 4 - Oct 5
Keldholme Cottages 2 - UK11488
A rustic brick building with a reception sign, a parked vehicle, and outdoor seating area.

13. 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 CA $159
CA $189 total
includes taxes & fees
Sep 28 - Sep 29
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
A traditional house with a tiled roof, a well-maintained lawn, and a stone wall.

14. 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 CA $541
CA $541 total
includes taxes & fees
Oct 1 - Oct 2
2 bedroom accommodation in Pickering
A stone building with a bay window, a door, and a small shop sign.

15. 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 CA $150
CA $179 total
includes taxes & fees
Oct 11 - Oct 12
Stoney Nook Cottage
A backyard with a wooden fence, a brick wall, and a grassy lawn.

16. Temple Hill View

Temple Hill View
3.0 star property
York
10.0 out of 10, Exceptional, (1 review)
"The house was lovely, spacious, clean and well stocked with anything you might need. It is in a tranquil village and has plentiful off-road parking. The garden has an excellent view and is so peaceful to sit in. There is a park 2 minutes down the lane, a football field, and if you continue down the lane, there is a pond and a lovely walk around it. It was perfectly located between all the walking areas I wanted to see and complete. When we arrived there was bread, milk and some treats waiting...
United Kingdom
Jade
The price is CA $971
CA $1,165 total
includes taxes & fees
Oct 2 - Oct 3
Temple Hill View
A brick building with multiple windows, a small garden area with potted plants, and a flag on the roof.

17. 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.
The price is CA $760
CA $760 total
includes taxes & fees
Oct 1 - Oct 2
2 bedroom accommodation in Pickering
A brick building with a tiled roof, outdoor seating, and potted plants.

18. 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
7.2 out of 10, Good, (9 reviews)
"Quirky. Most comfortable bed we've ever slept in."
United Kingdom
Leigh
The price is CA $346
CA $393 total
includes taxes & fees
Sep 28 - Sep 29
The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite

19. Mandarin Lodge - UK51936

Mandarin Lodge - UK51936
Yarm
The price is CA $568
CA $568 total
includes taxes & fees
Sep 28 - Sep 29
Mandarin Lodge - UK51936

20. Dove Lodge - UK51935

Dove Lodge - UK51935
Yarm
The price is CA $568
CA $568 total
includes taxes & fees
Sep 28 - Sep 29
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Helmsley Hotel Reviews

DoubleTree by Hilton York

DoubleTree by Hilton York

8/10 Good
"Parking not enough spaces at hotel charges were too expensive £25 per day stayed Friday 18:00 until 09:00 Sunday charged £50 not happy"
Sandra 2-night trip
Posted 23 hours ago
DoubleTree by Hilton York

Find out more about Helmsley

Helmsley Cottages information

Number of reviews
74
Accommodation
1732 Cottages
Lowest Price
CA $164
Highest Price
CA $1,279