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
The price is NT$18,706
NT$22,447 total
includes taxes & fees
Aug 11 - Aug 12
Cliff House
Cottage | Interior

2. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is NT$18,261
NT$21,913 total
includes taxes & fees
Aug 9 - Aug 10
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
The price is NT$10,578
NT$12,693 total
includes taxes & fees
Aug 9 - Aug 10
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
The price is NT$2,420
NT$2,904 total
includes taxes & fees
Aug 16 - Aug 17
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
The price is NT$1,917
NT$2,300 total
includes taxes & fees
Aug 20 - Aug 21
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
The price is NT$4,964
NT$4,964 total
includes taxes & fees
Aug 10 - Aug 11
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
The price is NT$2,915
NT$3,498 total
includes taxes & fees
Aug 16 - Aug 17
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
The price is NT$5,559
NT$6,671 total
includes taxes & fees
Aug 6 - Aug 7
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
The price is NT$2,241
NT$2,690 total
includes taxes & fees
Sep 4 - Sep 5
CoStays Aparthotel - Middlesbrough
View from property

10. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (303 reviews)
"Great place to stay and great location"
Canada
Christian
The price is NT$4,603
NT$5,524 total
includes taxes & fees
Aug 16 - Aug 17
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
The price is NT$3,420
NT$4,104 total
includes taxes & fees
Aug 8 - Aug 9
Costays Apartment Standard Double Studio
Cottage | Exterior

12. Walnut Cottage

Walnut Cottage
2.5 star property
York
The price is NT$11,859
NT$14,231 total
includes taxes & fees
Aug 17 - Aug 18
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
The price is NT$4,756
NT$8,323 total
includes taxes & fees
Aug 6 - Aug 7
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)
The price is NT$3,502
NT$7,723 total
includes taxes & fees
Aug 9 - Aug 10
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
The price is NT$1,917
NT$2,300 total
includes taxes & fees
Aug 6 - Aug 7
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
The price is NT$6,619
NT$7,943 total
includes taxes & fees
Aug 23 - Aug 24
18 Horner Street York
Interior

17. St. Anthonys

St. Anthonys
3.0 star property
York
The price is NT$24,052
NT$28,863 total
includes taxes & fees
Aug 26 - Aug 27
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
The price is NT$2,365
NT$2,838 total
includes taxes & fees
Aug 9 - Aug 10
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
The price is NT$8,160
NT$13,973 total
includes taxes & fees
Aug 13 - Aug 14
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
The price is NT$2,300
NT$2,300 total
includes taxes & fees
Aug 16 - Aug 17
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

The Minster Hotel York

The Minster Hotel York

8/10 Good
"N/A"
Lisa 1-night trip
Posted less than an hour ago
The Minster Hotel York

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia! You can easily find your home rentals, villas, holiday apartments in Helmsley using one of the methods below:

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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.