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
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Helmsley vacation rentals

Cottage | Interior

29 Bondgate

29 Bondgate
3.5 star property
York
The price is ₩858,649
₩1,030,379 total
includes taxes & fees
Jul 12 - Jul 13
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
The price is ₩879,592
₩1,055,510 total
includes taxes & fees
Jul 12 - Jul 13
Cliff House
Cottage | Interior

Ivy Cottage

Ivy Cottage
3.5 star property
York
The price is ₩1,022,700
₩1,227,240 total
includes taxes & fees
Jul 12 - Jul 13
Ivy Cottage
Room, Shared Bathroom (Dog Pod) | Exterior

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, (156 reviews)
"Everything was wonderful and amazing ill definetly be coming back "
United Kingdom
steffan
The price is ₩119,770
₩143,724 total
includes taxes & fees
Jul 5 - Jul 6
The Little Hide - Adult Only Camping Pods
Exterior

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 ₩233,757
₩233,757 total
includes taxes & fees
Jul 9 - Jul 10
Baby Moon
Bar (on property)

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.2 out of 10, Wonderful, (40 reviews)
"This was my fourth stay at Station Suites. It's good value and the staff are helpful and friendly. The rooms are great and the beds are really comfortable. "
United Kingdom
Colin
The price is ₩137,051
₩164,461 total
includes taxes & fees
Jul 10 - Jul 11
Station Suites
Superior Room, 1 Double Bed (Double Studio) | 1 bedroom, in-room safe, desk, iron/ironing board

CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.6 out of 10, Excellent, (8 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is ₩113,201
₩143,765 total
includes taxes & fees
Jul 3 - Jul 4
CoStays Aparthotel - Middlesbrough
Exterior

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 ₩261,789
₩314,147 total
includes taxes & fees
Jul 6 - Jul 7
Old Mill Tiny Homes
Studio | Dining

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 ₩90,255
₩108,306 total
includes taxes & fees
Jul 6 - Jul 7
Welbury Studio Retreat
Interior

Pippin Cottage

Pippin Cottage
3.0 star property
Ripon
The price is ₩525,312
₩630,374 total
includes taxes & fees
Jul 5 - Jul 6
Pippin Cottage
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
"I had a great stay at the Moxy York. The property is modern, creative, design-forward, and very clean. For those who prefer a more modern, contemporary hotel while visiting a historic city like York, this is a great choice. The location is excellent, right on the edge of the main old town. It is close enough to easily walk into the historic center, but just removed enough that it felt quiet at night with very little traffic. It is also next door to a very old historic pub, which ended up being a great bonus. The reception staff were very friendly and welcoming, and the free cocktail at check-in was a fun touch. My room was spacious, comfortable, and very clean, with a nice bathroom and plenty of space to settle in. The lobby is also fantastic. It is large, stylish, and full of different seating areas, whether you want to work, relax, or sit with a small group. It made the hotel feel very easy and comfortable to spend time in. The only small note is that the entrance/location can be a little awkward for Uber drop-offs and pickups. Drivers may stop slightly down the street, but there is a small pull-in area nearby that works well once you know where it is. Overall, this was a great hotel in a great area. I would absolutely stay here again. Wish I had stayed longer in York. So much to explore."
Matthew 1-night trip
Posted 3 hours ago
Moxy York

Find out more about Helmsley

Search for Vacation rentals in Helmsley on Expedia.co.uk! You can easily find your home rentals, villas, Vacation 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?

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 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.