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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Helmsley vacation rentals

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

1. Cliff House

Cliff House
3.5 star property
York
$576 nightly
The price is $692
Aug 23 - Aug 24
Total with taxes and fees
Cliff House
Cottage | Interior

2. 29 Bondgate

29 Bondgate
3.5 star property
York
$563 nightly
The price is $675
Aug 26 - Aug 27
Total with taxes and fees
29 Bondgate
Fridge, dishwasher, electric kettle, toaster

3. Lilac Cottage

Lilac Cottage
3.0 star property
York
10.0 out of 10, Exceptional, (1 review)
"Lovely cottage in a quiet village."
United States
Kevin
$326 nightly
The price is $391
Aug 13 - Aug 14
Total with taxes and fees
Lilac Cottage
Room, Shared Bathroom (Dog Pod) | Exterior

4. 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)
"Everything was wonderful and amazing ill definetly be coming back "
United Kingdom
steffan
$75 nightly
The price is $90
Aug 16 - Aug 17
Total with taxes and fees
The Little Hide - Adult Only Camping Pods
Studio | Dining

5. Welbury Studio Retreat

Welbury Studio Retreat
3.0 star property
Northallerton
9.4 out of 10, Exceptional, (3 reviews)
"Very helpful, we were going to be later than anticipated arriving, phoned to let them know, they reassured us it was no problem, everything was ready for our stay. Check-in at the bar was easy, staff showed us to our studio, staff very cheerful. Food in the pub was great, not just pub grub. Only downside, studio was small."
United Kingdom
Gillian
$57 nightly
The price is $68
Aug 20 - Aug 21
Total with taxes and fees
Welbury Studio Retreat
Exterior

6. Baby Moon

Baby Moon
2.0 star property
Guisborough
9.6 out of 10, Exceptional, (10 reviews)
"Really good customer service, the yurt was very comfortable. Good sites nearby to drive to (not walking distance)."
United Kingdom
Anonymous traveler
$153 nightly
The price is $153
Aug 9 - Aug 10
Total with taxes and fees
Baby Moon
Bar (on property)

7. Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (44 reviews)
"The property was really clean and the staff really friendly and helpful and a credit to the comoany"
United Kingdom
Sharon
$79 nightly
The price is $95
Aug 14 - Aug 15
Total with taxes and fees
Station Suites
Exterior

8. Old Mill Tiny Homes

Old Mill Tiny Homes
2.0 star property
Yarm
10.0 out of 10, Exceptional, (1 review)
"Spotlessly clean and so cosy Brilliant stay Lovely pub within walking distance "
United Kingdom
Caroline
$160 nightly
The price is $191
Aug 10 - Aug 11
Total with taxes and fees
Old Mill Tiny Homes
Superior Room, 1 Double Bed (Double Studio) | 1 bedroom, in-room safe, desk, iron/ironing board

9. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.8 out of 10, Excellent, (10 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
$69 nightly
The price is $83
Aug 21 - Aug 22
Total with taxes and fees
CoStays Aparthotel - Middlesbrough
View from property

10. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (304 reviews)
"Great place to stay and great location"
Canada
Christian
$135 nightly
The price is $162
Aug 9 - Aug 10
Total with taxes and fees
Goodramgate Apartments
House | 1 bedroom, laptop workspace, iron/ironing board

11. Costays Apartment Standard Double Studio

Costays Apartment Standard Double Studio
2.0 star property
Middlesbrough
$105 nightly
The price is $127
Aug 9 - Aug 10
Total with taxes and fees
Costays Apartment Standard Double Studio
Cottage | Exterior

12. Walnut Cottage

Walnut Cottage
2.5 star property
York
$366 nightly
The price is $439
Aug 17 - Aug 18
Total with taxes and fees
Walnut Cottage
Luxury Apartment, Ensuite (23) | Lounge

13. King's 23

King's 23
3.5 star property
City Centre
10.0 out of 10, Exceptional, (28 reviews)
"NA"
United Kingdom
Graham
$229 nightly
The price is $258
Aug 9 - Aug 10
Total with taxes and fees
King's 23
House | 2 bedrooms, high-speed internet

14. Host Stay The Surfer s Loft Apartment

Host Stay The Surfer s Loft Apartment
2.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1 review)
$193 nightly
The price is $231
Aug 9 - Aug 10
Total with taxes and fees
Host Stay The Surfer s Loft Apartment
Studio | Dining

15. Wellington Studio Retreat in Northallerton

Wellington Studio Retreat in Northallerton
3.0 star property
Northallerton
$58 nightly
The price is $70
Aug 9 - Aug 10
Total with taxes and fees
Wellington Studio Retreat in Northallerton
Interior

16. 18 Horner Street York

18 Horner Street York
3.0 star property
Clifton
9.2 out of 10, Wonderful, (9 reviews)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
Australia
Christina
$204 nightly
The price is $245
Aug 23 - Aug 24
Total with taxes and fees
18 Horner Street York
Interior

17. St. Anthonys

St. Anthonys
3.0 star property
York
$742 nightly
The price is $890
Aug 27 - Aug 28
Total with taxes and fees
St. Anthonys
Exterior

18. Vas's York House

Vas's York House
2.0 star property
Clifton
6.8 out of 10, (5 reviews)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
$73 nightly
The price is $87
Aug 9 - Aug 10
Total with taxes and fees
Vas's York House
House | 1 bedroom

19. Eldon Terrace - Luxury 1 Bedroom Property

Eldon Terrace - Luxury 1 Bedroom Property
2.0 star property
The Groves
$347 nightly
The price is $417
Aug 13 - Aug 14
Total with taxes and fees
Eldon Terrace - Luxury 1 Bedroom Property
Studio | Dining

20. Courtyard Rooms - Studio - Double Bed - Wifi

Courtyard Rooms - Studio - Double Bed - Wifi
3.0 star property
Northallerton
8.0 out of 10, Very Good, (2 reviews)
"Very friendly reception from the landlord Gareth who provided a most enlivening atmosphere in the Duke of Wellington ie a darts match for the men and Easter wreath making for the ladies. No food unfortunately but we found an excellent Italian restaurant in nearby Northallerton. The courtyard room was clean and comfortable, marred only by a very awkward shower - not easy to enter, due to lack of space."
United Kingdom
Alison
$65 nightly
The price is $65
Aug 17 - Aug 18
Total with taxes and fees
Courtyard Rooms - Studio - Double Bed - Wifi
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

Mercure York Fairfield Manor Hotel

Mercure York Fairfield Manor Hotel

8/10 Good
"What made our stay really great was the fact it was dog friendly, so we could take our dog with us."
Craig 3-night trip
Posted less than an hour 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 $83 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: Visitors like this Helmsley vacation home rental. It 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?

Howardian Hills and North York Moors National Park 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 Hemsley Walled Garden.

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.