A view of Helmsley, a market town and civil parish in the Ryedale district of North Yorkshire, England

Helmsley Vacation Rentals

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In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Helmsley vacation rentals

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Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
$516 nightly
The price is $516
Jun 24 - Jun 25
Total with taxes and fees
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Living area

Ivy Cottage, Helmsley

Ivy Cottage, Helmsley
Helmsley
10.0 out of 10, Exceptional, (2 reviews)
"We have been to Helmsley many times as my sister lived there for a few years. Since she moved back south we have been looking for somewhere to stay there. Ivy cottage ticked all the boxes. It is a lovely house in a perfect position with everything you could need. "
United Kingdom
Gillian A.
$688 nightly
The price is $688
Jun 27 - Jun 28
Total with taxes and fees
Ivy Cottage, Helmsley
Cottage | Interior

Ivy Cottage

Ivy Cottage
3.5 star property
York
$557 nightly
The price is $668
Jun 27 - Jun 28
Total with taxes and fees
Ivy Cottage
Outdoor dining

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.
$1,203 nightly
The price is $1,203
Jun 27 - Jun 28
Total with taxes and fees
8 Pottergate Mews, Helmsley
Cottage | Interior

29 Bondgate

29 Bondgate
3.5 star property
York
$553 nightly
The price is $664
Jul 12 - Jul 13
Total with taxes and fees
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
$567 nightly
The price is $680
Jul 12 - Jul 13
Total with taxes and fees
Cliff House
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
$146 nightly
The price is $146
Jun 24 - Jun 25
Total with taxes and fees
Baby Moon
Bar (on property)

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (38 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
$75 nightly
The price is $90
Jun 27 - Jun 28
Total with taxes and fees
Station Suites
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
$235 nightly
The price is $235
Jun 24 - Jun 25
Total with taxes and fees
Ensuite Family Cabin with Private Hot Tub
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
$154 nightly
The price is $185
Jul 9 - Jul 10
Total with taxes and fees
Old Mill Tiny Homes
Outdoor dining

The Byre is in Great Broughton

The Byre is in Great Broughton
Middlesbrough
$377 nightly
The price is $377
Jun 29 - Jun 30
Total with taxes and fees
The Byre is in Great Broughton
Interior

Pippin Cottage

Pippin Cottage
3.0 star property
Ripon
$339 nightly
The price is $406
Jul 4 - Jul 5
Total with taxes and fees
Pippin Cottage
Interior

North Terrace, Loftus

North Terrace, Loftus
Saltburn-by-the-Sea
$399 nightly
The price is $399
Jun 26 - Jun 27
Total with taxes and fees
North Terrace, Loftus
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, (24 reviews)
"It’s was a quiet and enjoyable place to stay, everything was private and provided for you. This made it very enjoyable to stay at."
United States
Freddie
$217 nightly
The price is $217
Jun 24 - Jun 25
Total with taxes and fees
Cosy Cabin with Hot Tub in North Yorkshire
Interior

Manor House Farm Cottage, Staithes

Manor House Farm Cottage, Staithes
Saltburn-by-the-Sea
$449 nightly
The price is $449
Jul 19 - Jul 20
Total with taxes and fees
Manor House Farm Cottage, Staithes
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
$381 nightly
The price is $381
Jul 6 - Jul 7
Total with taxes and fees
Glamping Pod in Yorkshire Wolds near York
Fireplace

Pheasant Cottage, Danby

Pheasant Cottage, Danby
Whitby
$659 nightly
The price is $659
Jun 25 - Jun 26
Total with taxes and fees
Pheasant Cottage, Danby
Outdoor dining

The Loft, Boroughbridge

The Loft, Boroughbridge
York
$352 nightly
The price is $352
Jul 1 - Jul 2
Total with taxes and fees
The Loft, Boroughbridge
Exterior

Glamping Pods in Yorkshire near York & Coast

Glamping Pods in Yorkshire near York & Coast
York
10.0 out of 10, Exceptional, (24 reviews)
"A lovely retreat! The living area was spacious enough for our family, and the modern amenities made our stay enjoyable, The garden was perfect for the kids to play,"
United States
Anonymous traveler
$381 nightly
The price is $381
Jul 6 - Jul 7
Total with taxes and fees
Glamping Pods in Yorkshire near York & Coast
Interior

Chapel Cottage: A Pet-Friendly Retreat

Chapel Cottage: A Pet-Friendly Retreat
Whitby
$367 nightly
The price is $367
Jul 1 - Jul 2
Total with taxes and fees
Chapel Cottage: A Pet-Friendly Retreat
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 Churchill Hotel

The Churchill Hotel

10/10 Excellent
"The staff were friendly and helpful at check-in and whenever we interacted with them. Our room was clean and in good condition. The outdoor beer garden was a great place to enjoy an afternoon drink, and family friendly for our five-year-old to join. The hotel was located a short distance from the Bootham Bar entrance to the city centre and conveniently located near other amenities."
Robert 3-night trip
Posted 4 hours ago
The Churchill Hotel

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 $86 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.

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 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.