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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Helmsley vacation 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 ￥72,588
￥87,106 total
includes taxes & fees
Oct 22 - Oct 23
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
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 ￥73,144
￥83,635 total
includes taxes & fees
Oct 22 - Oct 23
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A modern kitchen with white cabinetry, a Bosch oven, and a coffee machine.

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
The price is ￥132,187
￥143,517 total
includes taxes & fees
Nov 4 - Nov 5
Eighteen Pottergate - Beautiful cottage with garden central location
A modern living room with a fireplace, a television, a coffee table, and a sofa.

4. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
The price is ￥110,156
￥125,893 total
includes taxes & fees
Nov 3 - Nov 4
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A bedroom with a bed, a desk, a chair, a television, and a window.

5. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Hyland Cottage - sleeps 6 guests in 3 bedrooms
Helmsley
The price is ￥220,312
￥244,441 total
includes taxes & fees
Nov 8 - Nov 9
Hyland Cottage - sleeps 6 guests in 3 bedrooms
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 ￥87,747
￥105,296 total
includes taxes & fees
Oct 21 - Oct 22
29 Bondgate
A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

7. Cliff House

Cliff House
3.5 star property
York
The price is ￥89,887
￥107,864 total
includes taxes & fees
Oct 25 - Oct 26
Cliff House
A two-story stone house with a brick facade, surrounded by a garden with various plants and flowers.

8. Auburn House

Auburn House
3.5 star property
York
10.0 out of 10, Exceptional, (2 reviews)
"Lovely house with great facilities- has everything we could have needed to enjoy our stay. Quiet area but easy access to North Yorks Moors and other local attractions. "
United Kingdom
Stephen
The price is ￥115,569
￥138,683 total
includes taxes & fees
Nov 6 - Nov 7
Auburn House
A cozy, wooden interior with a dining area, kitchen, and a sofa by a large window overlooking a grassy landscape.

9. 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 ￥32,312
￥32,312 total
includes taxes & fees
Nov 1 - Nov 2
Cosy Rural Cabin with Private Hot Tub
A cozy living room with exposed wooden beams, a brick fireplace, a leather sofa, and a television.

10. 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 ￥48,888
￥48,888 total
includes taxes & fees
Oct 18 - Oct 19
2 bedroom accommodation in Pickering
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, (159 reviews)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
The price is ￥10,491
￥12,589 total
includes taxes & fees
Oct 18 - Oct 19
The Little Hide - Adult Only Camping Pods
A modern hotel lobby with a large digital display, seating areas, and a view of the interior.

12. Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (69 reviews)
"good parking, good breakfast, perfect for the train station, good size rooms"
United Kingdom
Alan
The price is ￥13,865
￥16,638 total
includes taxes & fees
Nov 5 - Nov 6
Station Suites
Two wooden pod-style cabins with large windows and seating areas, surrounded by a well-maintained lawn and trees.

13. 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 ￥48,211
￥48,211 total
includes taxes & fees
Nov 8 - Nov 9
Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
A staircase with white balusters, a door with a circular glass window, and a wall-mounted light fixture.

14. Middlesbrough Lodge

Middlesbrough Lodge
Middlesbrough
10.0 out of 10, Exceptional, (1 review)
"Nice room and straightforward checking in. Good value if you are on a budget. Small bedroom and bathroom but good well equipped shared kitchen with all facilities including washing machine with line and pegs outside if needed."
United Kingdom
Beatrice
The price is ￥7,081
￥9,756 total
includes taxes & fees
Oct 19 - Oct 20
Middlesbrough Lodge
A cozy, compact room with a loft bed, a small dining table, a bench, and a kitchenette.

15. 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 ￥36,486
￥36,486 total
includes taxes & fees
Nov 3 - Nov 4
Ensuite Family Cabin with Private Hot Tub
A historic stone archway with a sign for 'Monk Bar' visible in the background.

16. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (313 reviews)
"Great stay, was a perfect location in York. Good communication with host, clean and a good amount of room"
Canada
Erika
The price is ￥17,358
￥20,831 total
includes taxes & fees
Oct 18 - Oct 19
Goodramgate Apartments
A modern hotel room with a large bed, a balcony, and a view of the city at dusk.

17. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
7.4 out of 10, Good, (22 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is ￥10,556
￥13,512 total
includes taxes & fees
Oct 18 - Oct 19
CoStays Aparthotel - Middlesbrough
A brick building with a staircase, a door, and a window.

18. Croft Granary

Croft Granary
2.0 star property
York
10.0 out of 10, Exceptional, (5 reviews)
"We had a really good stay. The cottage is beautiful and equipped with absolutely everything you could ever need. Our son really enjoyed the garden, in particular the Wendy House which was also kitted out with toys, which was a lovely bonus. The village is peaceful but perfect for a nice walk. We would thoroughly recommend the property and would stay again. "
United Kingdom
Leslie
The price is ￥56,180
￥67,416 total
includes taxes & fees
Nov 1 - Nov 2
Croft Granary
A bedroom with a wooden bed, a desk, and a brick wall.

19. Preachers Yard

Preachers Yard
2.0 star property
City Centre
10.0 out of 10, Exceptional, (1 review)
"Tolle Wohnung und tolle Lage!"
Germany
Mario
The price is ￥28,326
￥51,406 total
includes taxes & fees
Nov 9 - Nov 10
Preachers Yard
A wooden cabin with a covered porch, a picnic table, and a large tree in the background.

20. Wigwam Holidays Cabin with Hot Tub and Pergola

Wigwam Holidays Cabin with Hot Tub and Pergola
Northallerton
The price is ￥44,062
￥48,258 total
includes taxes & fees
Nov 9 - Nov 10
Wigwam Holidays Cabin with Hot Tub and Pergola
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

10/10 Excellent
"Exceptional breakfast great location friendly staff"
Anne 1-night trip
Posted 8 hours ago
The Minster Hotel York

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:

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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.