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

Helmsley Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Helmsley vacation rentals

A stone house with a red-tiled roof, multiple windows, and a well-maintained garden with various plants and a stone wall.

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is AED 1,846
AED 2,215 total
includes taxes & fees
12 Dec - 13 Dec
Ivy Cottage
A stone cottage with a tiled roof, a wooden gate, and a sign indicating CCTV operation.

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

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
10.0 out of 10, Exceptional, (1 review)
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is AED 1,694
AED 1,840 total
includes taxes & fees
14 Nov - 15 Nov
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A bedroom with a bed, a window with a view, a wardrobe with louvered doors, and a hanging light fixture.

3. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A stone cottage with a tiled roof, a wooden door, and a small garden with a paved path.

4. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
Eighteen Pottergate - Beautiful cottage with garden central location
A room with a window, curtains, a bed, and two vases with flowers.

5. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Hyland Cottage - sleeps 6 guests in 3 bedrooms
Helmsley
Hyland Cottage - sleeps 6 guests in 3 bedrooms
A rustic stone building with a tiled roof, surrounded by lush greenery and a gravel path leading to the entrance.

6. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is AED 2,231
AED 2,678 total
includes taxes & fees
18 Nov - 19 Nov
29 Bondgate
A stone house with a red-tiled roof, a blue door, and a narrow stone pathway leading to the entrance.

7. Cliff House

Cliff House
3.5 star property
York
The price is AED 2,286
AED 2,743 total
includes taxes & fees
18 Nov - 19 Nov
Cliff House
A stone cottage with a wooden door and a sign reading "LILAC COTTAGE".

8. 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 AED 1,515
AED 1,818 total
includes taxes & fees
17 Nov - 18 Nov
Lilac Cottage
A small, single-story cabin with a sloped roof and a wooden door. It is surrounded by a well-maintained lawn and a gravel area with a fire pit.

9. Cosy Wigwam Holidays Cabin with Private Hot Tub

Cosy Wigwam Holidays 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 AED 748
AED 748 total
includes taxes & fees
15 Nov - 16 Nov
Cosy Wigwam Holidays Cabin with Private Hot Tub
A campsite with two cabins, each with a wooden deck and outdoor seating.

10. 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, (161 reviews)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
The price is AED 216
AED 259 total
includes taxes & fees
15 Nov - 16 Nov
The Little Hide - Adult Only Camping Pods
A stone house with a tiled roof, surrounded by a well-maintained lawn and dense greenery.

11. 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 AED 986
AED 986 total
includes taxes & fees
17 Nov - 18 Nov
Keldholme Cottage 1 - UK10992
A stone building with a red door, a stone wall, and a hedge.

12. 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 AED 1,686
AED 1,686 total
includes taxes & fees
14 Nov - 15 Nov
1 bedroom accommodation in Slingsby, near Malton
A spacious room with a large sliding glass door leading to an outdoor patio area.

13. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (317 reviews)
"Great place to stay and great location"
Canada
Christian
The price is AED 403
AED 484 total
includes taxes & fees
15 Nov - 16 Nov
Goodramgate Apartments
Two wooden pod-style cabins with large windows and seating areas, surrounded by a well-maintained lawn and trees.

14. 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 AED 1,005
AED 1,005 total
includes taxes & fees
15 Nov - 16 Nov
Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
A modern restaurant with high tables and blue chairs, a bar area, and a seating section with a sofa and tables.

15. Station Suites

Station Suites
3.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (72 reviews)
"good parking, good breakfast, perfect for the train station, good size rooms"
United Kingdom
Alan
The price is AED 299
AED 359 total
includes taxes & fees
20 Nov - 21 Nov
Station Suites
A bar area with a fireplace, stools, and a television screen displaying an outdoor scene.

16. Welbury Studio, Sleeps 2, Pet Friendly & Parking

Welbury Studio, Sleeps 2, Pet Friendly & Parking
3.0 star property
Northallerton
9.6 out of 10, Exceptional, (5 reviews)
"Very helpful, we were going to be later than anticipated arriving, phoned to let them know, they reassured us it was no problem, everything was ready for our stay. Check-in at the bar was easy, staff showed us to our studio, staff very cheerful. Food in the pub was great, not just pub grub. Only downside, studio was small."
United Kingdom
Gillian
The price is AED 225
AED 270 total
includes taxes & fees
15 Nov - 16 Nov
Welbury Studio, Sleeps 2, Pet Friendly & Parking
A modern living room with a brown sofa, a wall-mounted light, and a sliding glass door leading to an outdoor area.

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

Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Pickering
9.8 out of 10, Exceptional, (10 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 AED 806
AED 806 total
includes taxes & fees
15 Nov - 16 Nov
Foxtail Glamping Pod - sleeps 2 | Gold Award winning
A wooden cabin with a patio, surrounded by lush greenery and trees.

18. Ryedale Country Lodges - Willow Lodge

Ryedale Country Lodges - Willow Lodge
3.0 star property
York
10.0 out of 10, Exceptional, (2 reviews)
"A very cute lodge in a tranquil setting. Comfortable beds, great shower facilities and a great welcome pack was provided. We enjoyed watching the wide variety of birds including pheasants and red kites. "
United Kingdom
Erika
The price is AED 1,955
AED 2,346 total
includes taxes & fees
17 Nov - 18 Nov
Ryedale Country Lodges - Willow Lodge
A cozy wooden cabin with a hot tub, a fire pit, and a dining area.

19. Wigwam Holidays Cabin with Hot Tub and Pergola

Wigwam Holidays Cabin with Hot Tub and Pergola
Northallerton
The price is AED 967
AED 1,064 total
includes taxes & fees
16 Nov - 17 Nov
Wigwam Holidays Cabin with Hot Tub and Pergola
A modern hotel room with two beds, a TV, a desk, and a large mirror.

20. Costays Apartment Standard Double Studio

Costays Apartment Standard Double Studio
2.0 star property
Middlesbrough
The price is AED 340
AED 408 total
includes taxes & fees
15 Nov - 16 Nov
Costays Apartment Standard Double Studio
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

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

10/10 Excellent
"I always enjoy my visits. Staff is always welcoming and the location is perfect for all the trips I like to take Can’t wait to go back"
chiara 1-night trip
Posted less than an hour ago
Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

Frequently asked questions

Can I find vacation rentals in Helmsley?

Yes, we give you a choice of vacation rentals in Helmsley close to Helmsley Arts Centre, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation home rentals that Helmsley has to offer?

Vas's York House: You might want to consider this vacation home rental near Helmsley, which is equipped with a garden, daily housekeeping, and free WiFi to help you feel comfortable during your stay.

How many vacation rentals will I find in Helmsley?

With 7 Expedia vacation rentals, you're sure 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 Helmsley Castle and North York Moors National Park.

What are vacation rentals like in Helmsley?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Helmsley. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family gatherings.