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

Helmsley Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
$463 nightly
The price is $555
Oct 3 - Oct 4
Total with taxes and fees
Ivy Cottage
A cozy living room with a fireplace, a television, and comfortable seating.

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

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
$533 nightly
The price is $533
Sep 27 - Sep 28
Total with taxes and fees
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A modern kitchen with a built-in oven, a sink, and a window overlooking a garden.

3. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
$912 nightly
The price is $912
Sep 29 - Sep 30
Total with taxes and fees
Eighteen Pottergate - Beautiful cottage with garden central location
A modern kitchen with a built-in washing machine, a sink, and a window.

4. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
$797 nightly
The price is $797
Sep 27 - Sep 28
Total with taxes and fees
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

5. Cliff House

Cliff House
3.5 star property
York
$573 nightly
The price is $687
Oct 5 - Oct 6
Total with taxes and fees
Cliff House
A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

6. 29 Bondgate

29 Bondgate
3.5 star property
York
$559 nightly
The price is $671
Oct 21 - Oct 22
Total with taxes and fees
29 Bondgate
A compact kitchen with a washing machine, a sink, and a stove.

7. 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
$324 nightly
The price is $389
Oct 2 - Oct 3
Total with taxes and fees
Lilac Cottage
A cozy, wooden-framed room with a built-in bench and a view of a green field.

8. Cosy Rural Cabin with Private Hot Tub

Cosy Rural Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (8 reviews)
"Lovely pods, great area, nice and safe for the kids, everything provided, owners took us to feed the animals, bbq a great bonus"
United States
Alex
$239 nightly
The price is $239
Sep 27 - Sep 28
Total with taxes and fees
Cosy Rural Cabin with Private Hot Tub
A cozy living room with a fireplace, a leather sofa, a red throw pillow, a vase with flowers, and a wine glass on a wooden table.

9. Keldholme Cottage 1 - UK10992

Keldholme Cottage 1 - UK10992
Keldholme, near Kirkbymoorside
9.8 out of 10, Exceptional, (10 reviews)
"Excellent for get away from it all beautiful countryside and walks."
United States
John Kelly
$317 nightly
The price is $317
Sep 27 - Sep 28
Total with taxes and fees
Keldholme Cottage 1 - UK10992
A wooden hot tub with a bench and a glass of wine, surrounded by a wooden fence and foliage.

10. Ensuite Family Cabin with Private Hot Tub

Ensuite Family Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (4 reviews)
"This was such a fun experience. "
United States
Chantel
$237 nightly
The price is $237
Sep 27 - Sep 28
Total with taxes and fees
Ensuite Family Cabin with Private Hot Tub
A campsite with two cabins, each with a wooden deck and outdoor seating.

11. 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, (157 reviews)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
$64 nightly
The price is $76
Oct 4 - Oct 5
Total with taxes and fees
The Little Hide - Adult Only Camping Pods
Two wooden pod-style cabins with large windows and seating areas, surrounded by a well-maintained lawn and trees.

12. Daisy Family Glamping Pod | sleeps 4 - Gold Award winning

Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
Pickering
10.0 out of 10, Exceptional, (3 reviews)
"A great location. We stayed in a glamping pod and had a lovely time. Clean and all you need for a few days. Local shop 5 mins drive away to get anything you need"
United Kingdom
James E.
$346 nightly
The price is $346
Oct 1 - Oct 2
Total with taxes and fees
Daisy Family Glamping Pod | sleeps 4 - Gold Award winning
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

13. Heather Cottage - a beautiful cosy cottage

Heather Cottage - a beautiful cosy cottage
Snainton
10.0 out of 10, Exceptional, (1 review)
"Clean, organised flat in a lovely area. The hosts communication was great throughout, and there was a great guest book containing recommendations for the local area."
United Kingdom
Luigi
$162 nightly
The price is $162
Sep 28 - Sep 29
Total with taxes and fees
Heather Cottage - a beautiful cosy cottage
A modern living room with a brown sofa, a wall-mounted light, and a sliding glass door leading to an outdoor area.

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

Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Pickering
10.0 out of 10, Exceptional, (9 reviews)
"The pods have everything you need it’s clean modern, outside is kept neat and tidy, so relaxing, would definitely recommend and would come back again"
United Kingdom
Joy
$276 nightly
The price is $276
Oct 1 - Oct 2
Total with taxes and fees
Foxtail Glamping Pod - sleeps 2 | Gold Award winning
A patio with a table and chairs, surrounded by lush greenery and a wooden fence.

15. 1 bedroom accommodation in Slingsby, near Malton

1 bedroom accommodation in Slingsby, near Malton
Slingsby, near Malton
10.0 out of 10, Exceptional, (9 reviews)
"Lovely cottage. Welcoming and homely with everything provided that we needed. Good place for a relax and good walking for the dog."
United States
Carol Horne
$496 nightly
The price is $496
Oct 21 - Oct 22
Total with taxes and fees
1 bedroom accommodation in Slingsby, near Malton
A brick house with a garden, a white fence, and a clear sky.

16. Ceilidh Cottage

Ceilidh Cottage
3.5 star property
York
10.0 out of 10, Exceptional, (14 reviews)
"Lovely property in a lovely village - central to visit lots of interesting places."
United Kingdom
Barbara
$222 nightly
The price is $267
Sep 24 - Sep 25
Total with taxes and fees
Ceilidh Cottage
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

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
$694 nightly
The price is $833
Sep 27 - Sep 28
Total with taxes and fees
Temple Hill View
A picnic table and benches in a grassy outdoor area with trees and a clear sky.

18. Shepherds Rest - Shepherds hut - New for 2026

Shepherds Rest - Shepherds hut - New for 2026
3.0 star property
Saltburn-by-the-Sea
$135 nightly
The price is $162
Oct 19 - Oct 20
Total with taxes and fees
Shepherds Rest - Shepherds hut - New for 2026
A modern living room with a wooden staircase, a sofa, a table with a lamp, and a TV mounted on the wall.

19. Little Pythorn - UK45253

Little Pythorn - UK45253
Westerdale, near Castleton
9.8 out of 10, Exceptional, (7 reviews)
"A wonderful stay in a beautiful cottage. A really good relaxing break. Some excellent places to eat but remember you’re in the North YorkshireMoors. Lots of lovely walks around and places to visit.We will be back!"
United States
Kath W.
$338 nightly
The price is $338
Sep 27 - Sep 28
Total with taxes and fees
Little Pythorn - UK45253
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 Cottages 2 - UK11488
Keldholme, near Kirkbymoorside
10.0 out of 10, Exceptional, (9 reviews)
"Lovely and cosy cottage. Ideal for holiday stay. We thoroughly enjoyed our stay there."
United States
Kevin Jones
$391 nightly
The price is $391
Oct 4 - Oct 5
Total with taxes and fees
Keldholme Cottages 2 - UK11488
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

Mercure York Fairfield Manor Hotel

Mercure York Fairfield Manor Hotel

8/10 Good
"Bedroom and bathroom a bit dated when compared to comparable hotels. There was no USB bed side sockets which as really useful for guests with phones etc. Parking excellent with no charge. Good location for access to bus links to York City center."
John 3-night trip
Posted 11 hours ago
Mercure York Fairfield Manor Hotel

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 $61 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.