Helmsley Vacation Rentals from CA $121: Short-Term Rentals for 2026

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Helmsley vacation rentals

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Helmsley

CA $734 total

includes taxes & fees

Jun 22 - Jun 23

29 Bondgate

York

CA $934 total

includes taxes & fees

Jun 14 - Jun 15

Ivy Cottage, Helmsley

Helmsley

Gillian A.

CA $1,593 total

includes taxes & fees

Jun 27 - Jun 28

8 Pottergate Mews, Helmsley

York

Ian J.

CA $1,630 total

includes taxes & fees

Jun 12 - Jun 13

Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

York

CA $957 total

includes taxes & fees

Jun 28 - Jun 29

Ivy Cottage

York

CA $1,547 total

includes taxes & fees

Jun 27 - Jun 28

Room, Shared Bathroom (Dog Pod) | Exterior

The Little Hide - Adult Only Camping Pods

York

steffan

CA $130 total

includes taxes & fees

Jun 14 - Jun 15

Station Suites

Middlesbrough

Colin

CA $139 total

includes taxes & fees

Jun 27 - Jun 28

Welbury Studio Retreat

Northallerton

Gillian

CA $94 total

includes taxes & fees

Jun 12 - Jun 13

Baby Moon

Guisborough

Anonymous traveller

CA $206 total

includes taxes & fees

Jun 10 - Jun 11

Superior Room, 1 Double Bed (Double Studio)

CoStays Aparthotel - Middlesbrough

Middlesbrough

emma

CA $127 total

includes taxes & fees

Jun 21 - Jun 22

Ensuite Family Cabin with Private Hot Tub

Thirsk

Chantel

CA $330 total

includes taxes & fees

Jun 22 - Jun 23

Old Mill Tiny Homes

Yarm

Caroline

CA $272 total

includes taxes & fees

Jun 30 - Jul 1

Cosy Cabin with Hot Tub in North Yorkshire

Northallerton

Freddie

CA $283 total

includes taxes & fees

Jun 10 - Jun 11

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Holgate

Debbie M.

CA $234 total

includes taxes & fees

Jun 10 - Jun 11

The Byre is in Great Broughton

Middlesbrough

CA $530 total

includes taxes & fees

Jun 29 - Jun 30

Midsummer Cottage, Thornton Dale

Malton

CA $648 total

includes taxes & fees

Jun 11 - Jun 12

Luxury Cosy Cabin with Hot Tub in Rural Yorkshire

Northallerton

Sophie

CA $309 total

includes taxes & fees

Jun 10 - Jun 11

Glamping Pod in Yorkshire Wolds near York

York

Anonymous traveller

CA $538 total

includes taxes & fees

Jun 22 - Jun 23

Chapel Cottage: A Pet-Friendly Retreat

Whitby

CA $516 total

includes taxes & fees

Jul 1 - Jul 2

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Top Helmsley Hotel Reviews

The Minster Hotel York

8/10 Good

"More suited to the older population Im mid 30s so this wasn't really my style. However friendly staff clean room good distance from attractions"

Mercure York Fairfield Manor Hotel

6/10 Okay

"Very tired hotel needs updating, not great state of maintenance - moth holes in curtains, woodwork in bathroom rotten and bleached from damp, loudest extractor fan on the planet in the bathroom, no aircon, radiator with no controls under window (with broken window catch) , tiny tv with faulty screen (white patch about 10cm), 'double bed' two singles put together, empty screw holes on back of door where other chains/locks had been. Hotel restaurant empty on saturday night? No amenities - gym 2.2 miles down the road, no pool, had to wait for bar service as no-one in attendance. Amenities list in hotel room is details of the bus service into York. Overpriced and disappointing."

Gisborough Hall

6/10 Okay

"We were gifted a voucher as a maternity present and chose to spend it on a hotel. We decided on Gisborough Hall because of its promise of a luxury experience. The initial room did not feel luxurious and was more reminiscent of a standard chain hotel room than a premium country house hotel. Our view overlooked an active construction site with workers, building materials, and construction equipment. Upon request we were upgraded to a room with a forest view, which was appreciated. However, it left us wondering why guests who had already booked and paid were not allocated the better rooms in the first place. Were we treated differently because part of our stay had been paid for using a gifted voucher? Another major disappointment was the "king-size" beds, which are actually two separate mattresses pushed together. One of the reasons we chose Gisborough Hall was for the comfort and space a true king-size bed should provide as a family. This felt misleading. The Chaloner dinner service staff were attentive and professional throughout. The food itself was underwhelming. The duck was overcooked, lacking the flavour and quality expected, while the beef shin resembled a fillet rather than the slow-cooked, fall-apart texture one would associate with the dish. We also overheard diners at a neighbouring table making similar comments about their meal, suggesting our experience was not an isolated one. We left feeling that we had paid premium prices for a distinctly average experience."

Burn Hall Hotel

10/10 Excellent

"We had an absolutely fantastic stay at the Burn Hall Hotel from Thursday, 4 June to Sunday, 7 June. The staff were all very friendly and professional, and the service we received in the restaurant was superb. Really great waiters. The bar staff, Tom and Carina, were very good, friendly and welcoming. The room was great, clean and as expected, and the location of the hotel was ideal for our visits to York and a day trip to Whitby. The food was very good, and we enjoyed the breakfast, but especially the evening dinner. The food was great; very generous portions and of high quality. We travel extensively around the world, and our main home is in Florida. We have done many weekend breaks in the UK, and this was one of our favourites. We will definitely return to this hotel, maybe even this year. Thank you."

DoubleTree by Hilton York

2/10 Terrible

"This hotel should definitely not be classed as a 4⭐️ hotel. Was very very basic. We had to exchange rooms as our first room had damp on the coving and wallpaper coming away. Also spiders and cobwebs. We had to pay extra £20 for parking and our price of £169 did not even include breakfast. We had other friends also staying and 2 others couples had to swap rooms also. This hotel I would say is a basic 3⭐️ Avoid this hotel. I really wish we had read the reviews on the hotel before booking. DON’T BE FOOLED WITH THE WORD HILTON INCLUDED IN THE NAME.😡 Very disappointed"

Impossible Motel

8/10 Good

"This is a nice hotel, but not what we were expecting. The room was in the vault. It was atmospheric. But dark. The toilet is next to the head of the bed. And no door….. Even with the lights on it’s not bright. Only one key card per room. Which makes it difficult to go out and get stuff as the lights go off…."

Find out more about Helmsley

Everything you need to know about Helmsley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Helmsley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Helmsley vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Helmsley vacation rentals we have selected for you start as low as CA $121 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 vacation 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 vacation.

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.

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.

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Check prices for these dates

Our top choices for Helmsley vacation rentals

Beautiful stone cottage in the heart of Helmsley - sleeps 2

29 Bondgate

Ivy Cottage, Helmsley

8 Pottergate Mews, Helmsley

Cliff House

Ivy Cottage

The Little Hide - Adult Only Camping Pods

Station Suites

Welbury Studio Retreat

Baby Moon

CoStays Aparthotel - Middlesbrough

Ensuite Family Cabin with Private Hot Tub

Old Mill Tiny Homes

Cosy Cabin with Hot Tub in North Yorkshire

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

The Byre is in Great Broughton

Midsummer Cottage, Thornton Dale

Luxury Cosy Cabin with Hot Tub in Rural Yorkshire

Glamping Pod in Yorkshire Wolds near York

Chapel Cottage: A Pet-Friendly Retreat

Find vacation rentals that suit your style

Top Helmsley Hotel Reviews

The Minster Hotel York

Moxy York

Mercure York Fairfield Manor Hotel

Gisborough Hall

Burn Hall Hotel

The Golden Fleece Hotel, Thirsk, North Yorkshire

DoubleTree by Hilton York

Impossible Motel

The Feathers Hotel, Helmsley, North Yorkshire

Find out more about Helmsley

Frequently asked questions

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