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

Helmsley Holiday Rentals

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Check prices for these dates

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

Our top choices for Helmsley holiday rentals

A sunlit room with large windows, wicker furniture, and a rug.

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is HK$3,629
HK$4,355 total
includes taxes & fees
3 Oct - 4 Oct
Ivy Cottage
A cozy living room with a fireplace, a television, and comfortable seating.

2. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is HK$3,657
HK$4,181 total
includes taxes & fees
23 Sept - 24 Sept
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A modern kitchen with a built-in oven, a sink, and a window overlooking a garden.

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
The price is HK$6,609
HK$7,112 total
includes taxes & fees
28 Sept - 29 Sept
Eighteen Pottergate - Beautiful cottage with garden central location
A modern kitchen with a built-in washing machine, a sink, and a window.

4. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
The price is HK$5,507
HK$6,252 total
includes taxes & fees
27 Sept - 28 Sept
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

5. Cliff House

Cliff House
3.5 star property
York
The price is HK$4,494
HK$5,393 total
includes taxes & fees
1 Oct - 2 Oct
Cliff House
A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

6. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is HK$4,387
HK$5,264 total
includes taxes & fees
9 Oct - 10 Oct
29 Bondgate
A compact kitchen with a washing machine, a sink, and a stove.

7. 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 HK$2,541
HK$3,049 total
includes taxes & fees
2 Oct - 3 Oct
Lilac Cottage
A cozy, wooden-framed room with a built-in bench and a view of a green field.

8. Cosy Rural Cabin with Private Hot Tub

Cosy Rural Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (8 reviews)
"Lovely pods, great area, nice and safe for the kids, everything provided, owners took us to feed the animals, bbq a great bonus"
United States
Alex
The price is HK$1,875
HK$1,875 total
includes taxes & fees
23 Sept - 24 Sept
Cosy Rural Cabin with Private Hot Tub
A cozy living room with a fireplace, a leather sofa, a red throw pillow, a vase with flowers, and a wine glass on a wooden table.

9. 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 HK$2,490
HK$2,490 total
includes taxes & fees
27 Sept - 28 Sept
Keldholme Cottage 1 - UK10992
A wooden hot tub with a bench and a glass of wine, surrounded by a wooden fence and foliage.

10. Ensuite Family Cabin with Private Hot Tub

Ensuite Family Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (4 reviews)
"This was such a fun experience. "
United States
Chantel
The price is HK$1,861
HK$1,861 total
includes taxes & fees
23 Sept - 24 Sept
Ensuite Family Cabin with Private Hot Tub
A campsite with two cabins, each with a wooden deck and outdoor seating.

11. The Little Hide - Adult Only Camping Pods

The Little Hide - Adult Only Camping Pods
2.0 star property
York
9.2 out of 10, Wonderful, (157 reviews)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
The price is HK$498
HK$598 total
includes taxes & fees
4 Oct - 5 Oct
The Little Hide - Adult Only Camping Pods
Two wooden pod-style cabins with large windows and seating areas, surrounded by a well-maintained lawn and trees.

12. Daisy Family Glamping Pod | sleeps 4 - Gold Award winning

Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
Pickering
10.0 out of 10, Exceptional, (3 reviews)
"A great location. We stayed in a glamping pod and had a lovely time. Clean and all you need for a few days. Local shop 5 mins drive away to get anything you need"
United Kingdom
James E.
The price is HK$2,714
HK$2,714 total
includes taxes & fees
23 Sept - 24 Sept
Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
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
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 HK$797
HK$1,164 total
includes taxes & fees
28 Sept - 29 Sept
Heather Cottage - a beautiful cosy cottage
A modern living room with a brown sofa, a wall-mounted light, and a sliding glass door leading to an outdoor area.

14. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Pickering
10.0 out of 10, Exceptional, (9 reviews)
"The pods have everything you need it’s clean modern, outside is kept neat and tidy, so relaxing, would definitely recommend and would come back again"
United Kingdom
Joy
The price is HK$2,169
HK$2,169 total
includes taxes & fees
23 Sept - 24 Sept
Foxtail Glamping Pod - sleeps 2 | Gold Award winning
A patio with a table and chairs, surrounded by lush greenery and a wooden fence.

15. 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 HK$3,895
HK$3,895 total
includes taxes & fees
8 Oct - 9 Oct
1 bedroom accommodation in Slingsby, near Malton
A brick house with a garden, a white fence, and a clear sky.

16. Ceilidh Cottage

Ceilidh Cottage
3.5 star property
York
10.0 out of 10, Exceptional, (14 reviews)
"Lovely property in a lovely village - central to visit lots of interesting places."
United Kingdom
Barbara
The price is HK$1,740
HK$2,088 total
includes taxes & fees
24 Sept - 25 Sept
Ceilidh Cottage
A modern kitchen with a built-in dishwasher, a microwave, and a stove. There is a window providing a view of the outdoors.

17. 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 HK$5,448
HK$6,538 total
includes taxes & fees
27 Sept - 28 Sept
Temple Hill View
A picnic table and benches in a grassy outdoor area with trees and a clear sky.

18. Shepherds Rest - Shepherds hut - New for 2026

Shepherds Rest - Shepherds hut - New for 2026
3.0 star property
Saltburn-by-the-Sea
The price is HK$1,116
HK$1,339 total
includes taxes & fees
24 Sept - 25 Sept
Shepherds Rest - Shepherds hut - New for 2026
A modern living room with a wooden staircase, a sofa, a table with a lamp, and a TV mounted on the wall.

19. 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 HK$2,654
HK$2,654 total
includes taxes & fees
26 Sept - 27 Sept
Little Pythorn - UK45253
A kitchen with light green cabinets, a tiled backsplash, a stove, a toaster, and a window with a view of greenery.

20. 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 HK$3,064
HK$3,064 total
includes taxes & fees
4 Oct - 5 Oct
Keldholme Cottages 2 - UK11488
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
"Friendly, good rooms, good staff, good bar and good food"
Nicola 4-night trip
Posted 6 hours ago
Burn Hall Hotel

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia! You can easily find your home rentals, villas, holiday apartments in Helmsley using one of the methods below:

  • View our selection of featured holiday rentals in Helmsley
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  • Enter your travel dates to view the best deals on holiday rentals in Helmsley while they last

Look no further and take a look at our great range of rental properties in Helmsley!

Frequently asked questions

Can I find holiday rentals in Helmsley?

Yes, there are holiday rentals in Helmsley close to Helmsley Arts Centre, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and spas in Helmsley. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Helmsley has to offer?

Vas's York House: This holiday home rental outside of Helmsley is equipped with a garden, daily housekeeping and free WiFi to help you feel comfortable during your stay.

How many holiday rentals will I find in Helmsley?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Helmsley stay.

What can I see and do in Helmsley?

Hemsley Walled Garden and Howardian Hills are a couple of scenic spots to enjoy the outdoors, whereas Helmsley Arts Centre is one of the cultural attractions. Other places in town to visit include North York Moors National Park and Duncombe Park.

What are holiday rentals like in Helmsley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Helmsley. Holiday rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.