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

Helmsley Vacation Rentals

  • 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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Helmsley vacation rentals

A dining area with a wooden table set for four, surrounded by chairs. A vase with flowers is on the table, and there is a fireplace with a mantel to the left.

1. Cliff House

Cliff House
3.5 star property
York
The price is NT$18,499
NT$22,198 total
includes taxes & fees
Nov 19 - Nov 20
Cliff House
A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

2. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is NT$18,058
NT$21,670 total
includes taxes & fees
Nov 9 - Nov 10
29 Bondgate
A compact kitchen with a washing machine, a sink, and a stove.

3. 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 NT$12,809
NT$15,371 total
includes taxes & fees
Nov 16 - Nov 17
Lilac Cottage
A campsite with two cabins, each with a wooden deck and outdoor seating.

4. 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 NT$1,944
NT$2,333 total
includes taxes & fees
Nov 8 - Nov 9
The Little Hide - Adult Only Camping Pods
A compact hotel room with a kitchenette, a dining area, and a bed with a blue headboard.

5. Station Suites

Station Suites
4.0 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 NT$3,244
NT$3,893 total
includes taxes & fees
Nov 6 - Nov 7
Station Suites
A historic stone archway with a sign for 'Monk Bar' visible in the background.

6. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (316 reviews)
"Great place to stay and great location"
Canada
Christian
The price is NT$3,615
NT$4,338 total
includes taxes & fees
Nov 5 - Nov 6
Goodramgate Apartments
A two-story stone house with a brick facade, surrounded by a garden with various plants and flowers.

7. 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 NT$23,784
NT$28,540 total
includes taxes & fees
Nov 7 - Nov 8
Auburn House
A brick building with a sign for 'The Duke Of Wellington COURTYARD ROOMS.' There are picnic tables with umbrellas, a gravel courtyard, and a staircase leading to the entrance.

8. 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 NT$2,327
NT$2,792 total
includes taxes & fees
Nov 9 - Nov 10
Welbury Studio, Sleeps 2, Pet Friendly & Parking
A staircase with white balusters, a door with a circular glass window, and a wall-mounted light fixture.

9. 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 NT$1,639
NT$2,228 total
includes taxes & fees
Nov 6 - Nov 7
Middlesbrough Lodge
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

The Minster Hotel York

The Minster Hotel York

8/10 Good
"Very good stay at this hotel great location to York Centre everything within easy walking distance. Very good breakfast with plenty of options for £12 a day and on site parking for £10 a day plus good wifi . They are gradually refurbishing the rooms so some minor attention needed to repairs and bit more attention to cleaning and be full 5 stars. That said I would still stay here as it is now due to its location and excellent staff the small issues mentioned would not spoil your stay."
Paul 2-night trip
Posted 13 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:

  • View our selection of featured holiday rentals in Helmsley
  • Use the map to find apartments and other holiday homes in the Helmsley neighbourhood you prefer
  • 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 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.