Helmsley Vacation Rentals from $55: Search Short-Term Rentals

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

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Our top choices for Helmsley vacation rentals

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

1. Ivy Cottage

York

$458 nightly

Oct 3 - Oct 4

Total with taxes and fees

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

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

Helmsley

Helen H.

$495 nightly

Sep 30 - Oct 1

Total with taxes and fees

A modern living room with a fireplace, a television, a coffee table, and a sofa.

3. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY

$743 nightly

Sep 29 - Sep 30

Total with taxes and fees

A modern kitchen with white cabinetry, a Bosch oven, and a coffee machine.

4. Eighteen Pottergate - Beautiful cottage with garden central location

HELMSLEY

$870 nightly

Sep 29 - Sep 30

Total with taxes and fees

A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

5. Cliff House

York

$567 nightly

Oct 1 - Oct 2

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.

6. 29 Bondgate

York

$554 nightly

Oct 9 - Oct 10

Total with taxes and fees

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

7. Lilac Cottage

York

Kevin

$321 nightly

Oct 2 - Oct 3

Total with taxes and fees

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

8. The Little Hide - Adult Only Camping Pods

York

Steve

$55 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

Thirsk

Alex

$237 nightly

Sep 29 - Sep 30

Total with taxes and fees

A stone house with a tiled roof, surrounded by a well-maintained lawn and dense greenery.

10. Keldholme Cottage 1 - UK10992

Keldholme, near Kirkbymoorside

John Kelly

$344 nightly

Oct 21 - Oct 22

Total with taxes and fees

A bar area with a fireplace, stools, and a television screen displaying an outdoor scene.

11. Welbury Studio, Sleeps 2, Pet Friendly & Parking

Northallerton

Gillian

$60 nightly

Sep 29 - Sep 30

Total with taxes and fees

A staircase with white balusters, a door with a circular glass window, and a wall-mounted light fixture.

12. Middlesbrough Lodge

Middlesbrough

$46 nightly

Oct 1 - Oct 2

Total with taxes and fees

A stone building with a steeply pitched roof, a narrow street, and a clear sky.

13. Heather Cottage - a beautiful cosy cottage

Snainton

Luigi

$146 nightly

Sep 29 - Sep 30

Total with taxes and fees

A cozy, compact room with a loft bed, a small dining table, a bench, and a kitchenette.

14. Ensuite Family Cabin with Private Hot Tub

Thirsk

Chantel

$235 nightly

Sep 29 - Sep 30

Total with taxes and fees

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

15. 1 bedroom accommodation in Slingsby, near Malton

Slingsby, near Malton

Carol Horne

$492 nightly

Oct 8 - Oct 9

Total with taxes and fees

A two-story brick house with a bay window, a black front door, and satellite dishes on the roof.

16. Cosy, 2 Bedroom Cottage in Guisborough Town Centre

North Yorkshire

jane

$117 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern kitchen with a built-in dishwasher, a microwave, and a stove. There is a window providing a view of the outdoors.

17. Temple Hill View

York

"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...

Jade

$688 nightly

Oct 2 - Oct 3

Total with taxes and fees

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

18. CoStays Aparthotel - Middlesbrough

Middlesbrough

emma

$63 nightly

Oct 5 - Oct 6

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.

19. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

Pickering

Joy

$274 nightly

Sep 29 - Sep 30

Total with taxes and fees

A kitchen with light green cabinets, a tiled backsplash, a stove, a toaster, and a window with a view of greenery.

20. Keldholme Cottages 2 - UK11488

Keldholme, near Kirkbymoorside

Kevin Jones

$387 nightly

Oct 4 - Oct 5

Total with taxes and fees

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Top Helmsley Hotel Reviews

Burn Hall Hotel

10/10 Excellent

"The staff were absolutely lovely and very helpful. The room was good and clean, but the shower was a real problem… you couldn’t switch the mixer back to the bath, so had to run a bath from the showerhead. On arrival the bathroom contained 2 scrag-end rolls of toilet tissue and the toiletry bottles were dolls-house size. When we asked for the room to be serviced, they didn’t do the bed, which we had made up neat enough, but room service normally redoes it to immaculate standard! Dinner was nice, but a very limited menu. Breakfast was very good, with two notable exceptions: the coffee was extremely poor and weak. And the fruit juices (both apple and orange) were clearly watered down to half strength."

The Crown Hotel, Boroughbridge, North Yorkshire

8/10 Good

"Old coaching in so plenty of character. Unfortunately this also meant no lift so a bit of a struggle to upstairs rooms with a heavy suitcase. Staff were all friendly and efficient and the included breakfast offered plenty of variety. I ate dinner in the bar lady night and the lamb was really excellent. There is parking but I’m not sure if there is space if every room is filled. There’s also a spa on site but I didn’t have time to try it."

Mercure York Fairfield Manor Hotel

10/10 Excellent

"It's true it is a bit dated if that worries you, certainly didn't worry me, perfectly functional very clean, the only thing that bugged me was the Ruddy lift, second floor going down aagh first floor going up that voice done my head in I'm joking of course great location loads of parking, great staff, I'd stay here again."

Impossible Motel

8/10 Good

"My wife and I stayed in a suite on the second floor with a stand alone bathtub. The bath was a great feature but for the opulence of the room you'd expect a bigger sink (One of the tiny rectangular ones) not really in keeping with the standard and price. The bed was extremely big and comfortable, one of the best hotel beds we've stayed in. Location was extremely central but outside noise could be an issue for some (they do provide earplugs) The wifi was poor but that was a minor complaint. Overall it's an interesting place to stay for a night but it's overpriced for what it is."

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 $55 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.

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 North York Moors National Park and Duncombe 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

1. Ivy Cottage

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

3. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

4. Eighteen Pottergate - Beautiful cottage with garden central location

5. Cliff House

6. 29 Bondgate

7. Lilac Cottage

8. The Little Hide - Adult Only Camping Pods

9. Cosy Rural Cabin with Private Hot Tub

10. Keldholme Cottage 1 - UK10992

11. Welbury Studio, Sleeps 2, Pet Friendly & Parking

12. Middlesbrough Lodge

13. Heather Cottage - a beautiful cosy cottage

14. Ensuite Family Cabin with Private Hot Tub

15. 1 bedroom accommodation in Slingsby, near Malton

16. Cosy, 2 Bedroom Cottage in Guisborough Town Centre

17. Temple Hill View

18. CoStays Aparthotel - Middlesbrough

19. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

20. Keldholme Cottages 2 - UK11488

Find vacation rentals that suit your style

Top Helmsley Hotel Reviews

Burn Hall Hotel

The Crown Hotel, Boroughbridge, North Yorkshire

The Minster Hotel York

DoubleTree by Hilton York

Moxy York

Mercure York Fairfield Manor Hotel

The Feathers Hotel, Helmsley, North Yorkshire

Impossible Motel

Find out more about Helmsley

Frequently asked questions

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