Helmsley Vacation Rentals

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Helmsley vacation rentals

Smart TV, offices

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
$540 nightly
The price is $540
May 9 - May 10
Total with taxes and fees
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
$580 nightly
The price is $696
May 14 - May 15
Total with taxes and fees
Cliff House
Living area

8 Pottergate Mews, Helmsley

8 Pottergate Mews, Helmsley
York
8.0 out of 10, Very Good, (1 review)
"Great location just steps away from the market square, very convenient for exploring North Yorkshire. Property overall is good but having stayed a number of times there a few minor things that now need updating. Overall very good for visiting this area"
United Kingdom
Ian J.
$1,157 nightly
The price is $1,157
May 16 - May 17
Total with taxes and fees
8 Pottergate Mews, Helmsley
Cottage | Interior

29 Bondgate

29 Bondgate
3.5 star property
York
$567 nightly
The price is $680
May 21 - May 22
Total with taxes and fees
29 Bondgate
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, (153 reviews)
"Everything was wonderful and amazing ill definetly be coming back "
United Kingdom
steffan
$79 nightly
The price is $95
May 31 - Jun 1
Total with taxes and fees
The Little Hide - Adult Only Camping Pods
Terrace/patio

Ensuite Family Cabin with Private Hot Tub

Ensuite Family Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (4 reviews)
"This was such a fun experience. "
United States
Chantel
$240 nightly
The price is $240
May 10 - May 11
Total with taxes and fees
Ensuite Family Cabin with Private Hot Tub
Terrace/patio

Cosy Cabin with Hot Tub in North Yorkshire

Cosy Cabin with Hot Tub in North Yorkshire
Northallerton
9.6 out of 10, Exceptional, (23 reviews)
"Really beautiful surroundings and accommodation. Really quiet and peaceful, just what we needed. Attentive hosts to go with it. Thank you so much. "
United Kingdom
James C.
$206 nightly
The price is $206
May 11 - May 12
Total with taxes and fees
Cosy Cabin with Hot Tub in North Yorkshire
Cabin | Exterior

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
$83 nightly
The price is $100
May 10 - May 11
Total with taxes and fees
5m xl Bell Tent With log Burner, Near Whitby
Exterior

Glamping Pod in Yorkshire Wolds near York

Glamping Pod in Yorkshire Wolds near York
York
9.4 out of 10, Exceptional, (48 reviews)
"The kitchen setup was well thought out, We made several meals during our stay and found everything we needed,"
United States
Anonymous traveler
$404 nightly
The price is $404
May 11 - May 12
Total with taxes and fees
Glamping Pod in Yorkshire Wolds near York
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
$151 nightly
The price is $151
Jun 8 - Jun 9
Total with taxes and fees
Baby Moon
LCD TV

Foxtail Glamping Pod - sleeps 2 | Gold Award winning

Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"The pods have everything you need it’s clean modern, outside is kept neat and tidy, so relaxing, would definitely recommend and would come back again"
United Kingdom
Joy
$307 nightly
The price is $307
May 13 - May 14
Total with taxes and fees
Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Interior

Dragonstone Lodge

Dragonstone Lodge
3.0 star property
Northallerton
10.0 out of 10, Exceptional, (1 review)
"We loved this property. The owners obviously have an eye for decor as it is a really stylish place and beautifully finished. We loved how peaceful the property was and the owners had thought of everything . We really appreciated the tea, coffee and milk after a 5 hour drive and the muffins, biscuits and crisps were a lovely touch. All the information you needed was in a folder and we visited lots of the places recommenced in it. It’s a fantastic property and we hope to stay there again."
United Kingdom
Mark
$306 nightly
The price is $368
May 20 - May 21
Total with taxes and fees
Dragonstone Lodge
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
8.0 out of 10, Very Good, (6 reviews)
"Room was lovely and spotless. A staff member also made sure we got into the building and room as we arrived late. Would highly recommend."
United Kingdom
Sam
$77 nightly
The price is $92
May 9 - May 10
Total with taxes and fees
CoStays Aparthotel - Middlesbrough
WiFi

The Loft, Boroughbridge

The Loft, Boroughbridge
York
$367 nightly
The price is $367
May 11 - May 12
Total with taxes and fees
The Loft, Boroughbridge
Fireplace

The Byre is in Great Broughton

The Byre is in Great Broughton
Middlesbrough
$393 nightly
The price is $393
May 12 - May 13
Total with taxes and fees
The Byre is in Great Broughton
WiFi

Charming Cow Byre Cottage Getaway

Charming Cow Byre Cottage Getaway
Pickering
$390 nightly
The price is $390
Jun 6 - Jun 7
Total with taxes and fees
Charming Cow Byre Cottage Getaway
Living area

North Terrace, Loftus

North Terrace, Loftus
Saltburn-by-the-Sea
$475 nightly
The price is $475
May 11 - May 12
Total with taxes and fees
North Terrace, Loftus
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
$59 nightly
The price is $70
May 10 - May 11
Total with taxes and fees
Welbury Studio Retreat
Living area

Midsummer Cottage, Thornton Dale

Midsummer Cottage, Thornton Dale
Malton
$481 nightly
The price is $481
May 18 - May 19
Total with taxes and fees
Midsummer Cottage, Thornton Dale
Outdoor dining

The Cottage, Thornton Dale

The Cottage, Thornton Dale
Pickering
$497 nightly
The price is $497
May 16 - May 17
Total with taxes and fees
The Cottage, Thornton Dale
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

Hampton by Hilton Stockton on Tees

Hampton by Hilton Stockton on Tees

10/10 Excellent
"Excellent location for a local gig, wide range of breakfast items and everything was fresh and hot. The staff were very friendly and helpful, rooms were immaculate and quiet. I thought that £7 parking overnight was a bit steep though. "
Louise 1-night trip
Posted 8 hours ago
Hampton by Hilton Stockton on Tees

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 $88 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.

Explore a world of travel with Expedia

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 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.