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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Helmsley vacation rentals

Cottage | Interior

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is NT$14,746
NT$17,695 total
includes taxes & fees
Oct 3 - Oct 4
Ivy Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

2. Cliff House

Cliff House
3.5 star property
York
The price is NT$18,254
NT$21,905 total
includes taxes & fees
Oct 4 - Oct 5
Cliff House
Cottage | Interior

3. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is NT$17,819
NT$21,383 total
includes taxes & fees
Oct 9 - Oct 10
29 Bondgate
Fridge, dishwasher, electric kettle, toaster

4. 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
The price is NT$10,322
NT$12,387 total
includes taxes & fees
Oct 2 - Oct 3
Lilac Cottage
Room, Shared Bathroom (Dog Pod) | 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)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
The price is NT$2,130
NT$2,557 total
includes taxes & fees
Oct 4 - Oct 5
The Little Hide - Adult Only Camping Pods
Interior

6. Middlesbrough Lodge

Middlesbrough Lodge
Middlesbrough
The price is NT$1,439
NT$1,982 total
includes taxes & fees
Oct 1 - Oct 2
Middlesbrough Lodge
Cabin | Exterior

7. 5m xl Bell Tent With log Burner, Near Whitby

5m xl Bell Tent With log Burner, Near Whitby
3.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1 review)
"What a lovely place, we hired a beautiful Bell tent for 2 nights. It was set up with all the essentials on our arrival. The plot had plenty of space around to set up bbq room and room for kids to play. The site, washrooms and kitchen were like new, very well maintained regularly cleaned. I have a pet allergy so the no pets policy was a great bonus here for me too. We had a great time and will book again. Thank you. "
United Kingdom
Jenna
The price is NT$2,622
NT$3,147 total
includes taxes & fees
Sep 20 - Sep 21
5m xl Bell Tent With log Burner, Near Whitby
Exterior

8. 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
The price is NT$7,066
NT$8,479 total
includes taxes & fees
Sep 24 - Sep 25
Ceilidh Cottage
Fridge, dishwasher, electric kettle, toaster

9. 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 NT$22,129
NT$26,555 total
includes taxes & fees
Sep 27 - Sep 28
Temple Hill View
Superior Room, 1 Double Bed (Double Studio) | 1 bedroom, in-room safe, desk, iron/ironing board

10. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.0 out of 10, Very good, (17 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is NT$2,015
NT$2,419 total
includes taxes & fees
Oct 4 - Oct 5
CoStays Aparthotel - Middlesbrough
Bar (on property)

11. Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (66 reviews)
"good parking, good breakfast, perfect for the train station, good size rooms"
United Kingdom
Alan
The price is NT$3,164
NT$3,796 total
includes taxes & fees
Sep 26 - Sep 27
Station Suites
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

Moxy York

Moxy York

10/10 Excellent
"."
Rebecca 1-night trip
Posted 15 hours ago
Moxy 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:

  • View our selection of featured holiday rentals in Helmsley
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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: 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.