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

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Our top choices for Helmsley holiday rentals

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is £415
includes taxes & fees
3 Oct - 4 Oct
Ivy Cottage

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 £397
includes taxes & fees
23 Sept - 24 Sept
Beautiful stone cottage in the heart of Helmsley - sleeps 2

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
The price is £689
includes taxes & fees
28 Sept - 29 Sept
Eighteen Pottergate - Beautiful cottage with garden central location

4. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
The price is £605
includes taxes & fees
27 Sept - 28 Sept
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

5. Cliff House

Cliff House
3.5 star property
York
The price is £514
includes taxes & fees
1 Oct - 2 Oct
Cliff House

6. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is £502
includes taxes & fees
9 Oct - 10 Oct
29 Bondgate

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 £291
includes taxes & fees
2 Oct - 3 Oct
Lilac Cottage

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 £179
includes taxes & fees
23 Sept - 24 Sept
Cosy Rural Cabin with Private Hot Tub

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 £237
includes taxes & fees
27 Sept - 28 Sept
Keldholme Cottage 1 - UK10992

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 £177
includes taxes & fees
23 Sept - 24 Sept
Ensuite Family Cabin with Private Hot Tub

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 £57
includes taxes & fees
4 Oct - 5 Oct
The Little Hide - Adult Only Camping Pods

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 £259
includes taxes & fees
23 Sept - 24 Sept
Daisy Family Glamping Pod | sleeps 4 - Gold Award winning

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 £111
includes taxes & fees
28 Sept - 29 Sept
Heather Cottage - a beautiful cosy cottage

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 £207
includes taxes & fees
23 Sept - 24 Sept
Foxtail Glamping Pod - sleeps 2 | Gold Award winning

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 £371
includes taxes & fees
8 Oct - 9 Oct
1 bedroom accommodation in Slingsby, near Malton

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 £199
includes taxes & fees
24 Sept - 25 Sept
Ceilidh Cottage

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 £623
includes taxes & fees
27 Sept - 28 Sept
Temple Hill View

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 £123
includes taxes & fees
24 Sept - 25 Sept
Shepherds Rest - Shepherds hut - New for 2026

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 £253
includes taxes & fees
26 Sept - 27 Sept
Little Pythorn - UK45253

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 £292
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

Find out more about Helmsley

Everything you need to know about Helmsley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Helmsley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Helmsley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Helmsley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Helmsley. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Helmsley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Helmsley holiday rentals we have selected for you start as low as £43 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Helmsley rentals

At Expedia, we put the best Helmsley holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Helmsley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Helmsley holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Helmsley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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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.