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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 P28,762
P34,515 total
includes taxes & fees
Oct 22 - Oct 23
Ivy Cottage
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 P34,769
P41,723 total
includes taxes & fees
Oct 22 - Oct 23
29 Bondgate
A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

3. Cliff House

Cliff House
3.5 star property
York
The price is P35,644
P42,772 total
includes taxes & fees
Oct 18 - Oct 19
Cliff House
A compact kitchen with a washing machine, a sink, and a stove.

4. 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 P24,664
P29,596 total
includes taxes & fees
Oct 14 - Oct 15
Lilac Cottage
A modern hotel lobby with a large digital display, seating areas, and a view of the interior.

5. 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 P6,173
P7,408 total
includes taxes & fees
Oct 16 - Oct 17
Station Suites
A campsite with two cabins, each with a wooden deck and outdoor seating.

6. 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 P4,157
P4,988 total
includes taxes & fees
Oct 18 - Oct 19
The Little Hide - Adult Only Camping Pods
A historic stone archway with a sign for 'Monk Bar' visible in the background.

7. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (312 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 P6,516
P7,819 total
includes taxes & fees
Oct 11 - Oct 12
Goodramgate Apartments
A modern kitchen with a built-in dishwasher, a microwave, and a stove. There is a window providing a view of the outdoors.

8. 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 P43,179
P51,815 total
includes taxes & fees
Oct 14 - Oct 15
Temple Hill View
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 P2,806
P3,866 total
includes taxes & fees
Oct 12 - Oct 13
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.
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Top Helmsley Hotel Reviews

The Crown Hotel, Boroughbridge, North Yorkshire

The Crown Hotel, Boroughbridge, North Yorkshire

8/10 Good
"Have stayed several times. Good value and well located near the A1. Staff helpful and pleasant. Cleanliness top notch. Will continue to stay there. Easy reach of York."
richard 2-night trip
Posted 1 hour ago
The Crown Hotel, Boroughbridge, North Yorkshire

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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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.