Helmsley Vacation Rentals from $71: Search Short-Term Rentals

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Our top choices for Helmsley vacation rentals

A bedroom with a bed, a window with a view, a wardrobe with louvered doors, and a hanging light fixture.

1. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY

$667 nightly

Nov 24 - Nov 25

Total with taxes and fees

A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

2. 29 Bondgate

York

$613 nightly

Nov 13 - Nov 14

Total with taxes and fees

A stone building with a patio area featuring a table and chairs.

3. Hyland Cottage - sleeps 6 guests in 3 bedrooms

Helmsley

$1,480 nightly

Nov 15 - Nov 16

Total with taxes and fees

A cozy living room with a fireplace, a television, and comfortable seating.

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

Helmsley

Helen H.

$492 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bathroom with a window, a sink, a mirror, a vase with flowers, and a towel rack.

5. Eighteen Pottergate - Beautiful cottage with garden central location

HELMSLEY

$888 nightly

Nov 16 - Nov 17

Total with taxes and fees

A sunlit room with large windows, wicker furniture, and a rug.

6. Ivy Cottage

York

$507 nightly

Dec 5 - Dec 6

Total with taxes and fees

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.

7. Cliff House

York

$628 nightly

Nov 18 - Nov 19

Total with taxes and fees

A glass on a hot tub with a view of a green field and mountains in the background.

8. Cosy Rural Cabin with Private Hot Tub

Thirsk

Alex

$206 nightly

Nov 10 - Nov 11

Total with taxes and fees

A two-story stone house with a brick facade, surrounded by a garden with various plants and flowers.

9. Auburn House

York

Stephen

$808 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden structure with a curved roof and a hot tub on a wooden deck.

10. Ensuite Family Cabin with Private Hot Tub

Thirsk

Chantel

$232 nightly

Nov 10 - Nov 11

Total with taxes and fees

A compact kitchen with white cabinets, a microwave, a toaster, and a sink.

11. Keldholme Cottage 1 - UK10992

Keldholme, near Kirkbymoorside

John Kelly

$271 nightly

Nov 17 - Nov 18

Total with taxes and fees

A patio with a table and chairs, surrounded by lush greenery and a wooden fence.

12. 1 bedroom accommodation in Slingsby, near Malton

Slingsby, near Malton

Carol Horne

$463 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

Pickering

James E.

$276 nightly

Nov 10 - Nov 11

Total with taxes and fees

A campsite with two cabins, each with a wooden deck and outdoor seating.

14. The Little Hide - Adult Only Camping Pods

York

Steve

$59 nightly

Nov 15 - Nov 16

Total with taxes and fees

A two-story stone house with a red-tiled roof, multiple windows, and doors.

15. Keldholme Cottages 2 - UK11488

Keldholme, near Kirkbymoorside

Kevin Jones

$324 nightly

Nov 11 - Nov 12

Total with taxes and fees

A compact hotel room with a kitchenette, a dining area, and a bed with a blue headboard.

16. Station Suites

Middlesbrough

Alan

$81 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Pickering

Joy

$221 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern hotel room with two beds, a TV, a desk, and a large mirror.

18. Costays Apartment Standard Double Studio

Middlesbrough

$93 nightly

Nov 15 - Nov 16

Total with taxes and fees

A compact kitchen with a washing machine, a sink, and a stove.

19. Lilac Cottage

York

Kevin

$435 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern hotel room with a large bed, a balcony, and a view of the city at dusk.

20. CoStays Aparthotel - Middlesbrough

Middlesbrough

emma

$73 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Find vacation rentals that suit your style

Top Helmsley Hotel Reviews

A bedroom with a large bed, a nightstand with a lamp, and framed artwork on the wall.

The Feathers Hotel, Helmsley, North Yorkshire

York

10/10 Excellent

christina

A neatly made bed with a grey blanket, two bedside tables with lamps, and a wooden ceiling beam.

The Stapylton Arms

York

10/10 Excellent

Kimberlee

A bedroom with a large bed, a sofa, a TV, and a view of the outdoors.

Brickfields Farm

York

10/10 Excellent

Anonymous traveler

A room with a large arched window, a bench, two chairs, and a table with a vase.

Grays Court

City Centre

10/10 Excellent

Timothy

A covered outdoor seating area with wicker furniture, a ceiling projector, and a view of a green landscape.

Newsham Grange Farm Bed and Breakfast

Thirsk

10/10 Excellent

This B&B excelled in every way. As grandparents traveling with a twelve-year old, we praise Sue and staff in making us feel beyond welcome. The pool and the outdoor heated tub absorbed much of our granddaughter's excess energy, as did playing with the resident Rottweiler Axel. The grounds are lovely-lots of holly and ivy- and the rooms, immaculate and full of charm. The traditional Yorkshire breakfast is a plus for hardy appetites.

Noney

A stone house with a tiled roof, a white door with the number 9, and a window with curtains.

The Horseshoe Inn

Pickering

10/10 Excellent

gabe

A bedroom with a bed, two wall-mounted paintings, bedside lamps, and a neatly made bed with folded towels.

The Union Inn & Restaurant

Malton

10/10 Excellent

We decide to stay at Molton, not York due to the relatively higher price of the York hotel and our trip plan. It proves to be a good choice. The property located in a small and quiet town with about 10-15 minutes walk to the railway station. It may look normal from outside but when you step in, you would be impressed by the warm and cozy atmosphere. The first floor is the restaurant and a bar, with so many selections. The room was super clean and you can tell everything was so well maintained. ...

qiang

A hallway with a checkered floor, a chandelier, a radiator, and a door with a stained glass window.

MonkBridge House

The Groves

10/10 Excellent

Stephanie

A building with a sign reading "EN SUITE ACCOMMODATION" and flower baskets on the wall.

The Royal Oak Inn

York

10/10 Excellent

Robert

A bedroom with two single beds, a nightstand with a lamp, and a window with curtains.

Fourways Guest House

Thirsk

10/10 Excellent

Karen

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Helmsley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $71 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.