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

Helmsley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 P36,047
P43,256 total
includes taxes & fees
Sep 7 - Sep 8
Cliff House
Interior

2. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is P35,188
P42,226 total
includes taxes & fees
Sep 12 - Sep 13
29 Bondgate
Interior

3. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is P48,420
P58,104 total
includes taxes & fees
Sep 12 - Sep 13
Ivy Cottage
Exterior

4. Walnut Cottage

Walnut Cottage
2.5 star property
York
Walnut Cottage
Exterior

5. 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 P4,663
P5,595 total
includes taxes & fees
Sep 6 - Sep 7
The Little Hide - Adult Only Camping Pods
1 bedroom, in-room safe, desk, iron/ironing board

6. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
9.0 out of 10, Wonderful, (13 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is P4,627
P5,923 total
includes taxes & fees
Aug 28 - Aug 29
CoStays Aparthotel - Middlesbrough
Bar (on property)

7. Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (51 reviews)
"good parking, good breakfast, perfect for the train station, good size rooms"
United Kingdom
Alan
The price is P5,617
P6,740 total
includes taxes & fees
Sep 5 - Sep 6
Station Suites
Dining

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

Welbury Studio, Sleeps 2, Pet Friendly & Parking
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 P3,699
P4,439 total
includes taxes & fees
Aug 31 - Sep 1
Welbury Studio, Sleeps 2, Pet Friendly & Parking
3 bedrooms

9. Host Stay Finch House

Host Stay Finch House
2.0 star property
Middlesbrough
The price is P40,783
P49,264 total
includes taxes & fees
Sep 21 - Sep 22
Host Stay Finch House
Exterior

10. 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 P9,580
P9,580 total
includes taxes & fees
Aug 26 - Aug 27
Baby Moon
Exterior

11. 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 P10,728
P12,874 total
includes taxes & fees
Sep 8 - Sep 9
Old Mill Tiny Homes
1 bedroom, laptop workspace, iron/ironing board

12. Costays Apartment Standard Double Studio

Costays Apartment Standard Double Studio
2.0 star property
Middlesbrough
The price is P6,589
P7,907 total
includes taxes & fees
Aug 28 - Aug 29
Costays Apartment Standard Double Studio
Fridge, dishwasher, electric kettle, toaster

13. 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
The price is P43,699
P52,439 total
includes taxes & fees
Aug 31 - Sep 1
Temple Hill View
Interior

14. 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 P14,773
P17,727 total
includes taxes & fees
Sep 2 - Sep 3
18 Horner Street York
Miscellaneous

15. Penleys Apartment

Penleys Apartment
3.5 star property
The Groves
10.0 out of 10, Exceptional, (17 reviews)
"Excellent apartment within easy walking to all York attractions and parking spot available."
United Kingdom
Christine
Penleys Apartment
View from property

16. Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (307 reviews)
"Great place to stay and great location"
Canada
Christian
The price is P7,328
P8,794 total
includes taxes & fees
Aug 31 - Sep 1
Goodramgate Apartments
Dishwasher, cookware/dishes/utensils

17. Tuft House

Tuft House
2.0 star property
York
The price is P172,509
P207,010 total
includes taxes & fees
Aug 31 - Sep 1
Tuft House
Dining

18. Wellington Studio, Sleeps 2, Pets Ok, Free Parking

Wellington Studio, Sleeps 2, Pets Ok, Free Parking
3.0 star property
Northallerton
6.0 out of 10, (1 review)
"Location worked well for us. Small room with en-suite. Out the back for a country pub. Ample parking nearby. Room not great at keeping noise out - could hear footsteps overhead from residents upstairs and voices carried across the count yard late at night. As it was warm needed to windows open so more easily disturbed by noise. The bed was super creaky too, which was annoying and disturbing in the dead of night! Convenient and suitable for a location/budget stay. Friendly staff and looked like a...
United Kingdom
Ruth
The price is P3,699
P4,439 total
includes taxes & fees
Aug 31 - Sep 1
Wellington Studio, Sleeps 2, Pets Ok, Free Parking
1 bedroom

19. Eldon Terrace - Luxury 1 Bedroom Property

Eldon Terrace - Luxury 1 Bedroom Property
2.0 star property
The Groves
Eldon Terrace - Luxury 1 Bedroom Property
Living area

20. Riverbank View

Riverbank View
4.0 star property
The Groves
10.0 out of 10, Exceptional, (25 reviews)
"Great location, lovely owners and a lovely place to stay 👍"
United Kingdom
chris
The price is P15,706
P18,848 total
includes taxes & fees
Sep 21 - Sep 22
Riverbank View
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

The Black Swan - The Inn Collection Group

The Black Swan - The Inn Collection Group

10/10 Excellent
"food great too"
keith 1-night trip
Posted 7 hours ago
The Black Swan - The Inn Collection Group

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:

  • View our selection of featured holiday rentals in Helmsley
  • Use the map to find apartments and other holiday homes in the Helmsley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Helmsley while they last

Look no further and take a look at our great range of rental properties in Helmsley!

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 Duncombe Park and Helmsley Castle.

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.