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Helmsley Vacation Rentals

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    Upfront pricing

    We're not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Helmsley

Our top choices for Helmsley vacation rentals

The Little Hide - Adult Only Camping Pods
Room, Shared Bathroom (Posh Pod) | 1 bedroom

The Little Hide - Adult Only Camping Pods

2.0 star property
9.2 out of 10, Wonderful, (143)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
$78 nightly
The price is $94
Sep 7 - Sep 8
Total with taxes and fees
The Little Hide - Adult Only Camping Pods
Malton Central Apartments
Superior Apartment, Ensuite (Yorkersgate) | Interior

Malton Central Apartments

3.0 star property
8.8 out of 10, Excellent, (31)
"Again, another great stay and would highly recommend"
Malton Central Apartments
Morndyke Shepherds' Huts
1 bedroom, premium bedding, individually decorated

Morndyke Shepherds' Huts

3.5 star property
9.8 out of 10, Exceptional, (19)
"Lovely place to stay, very relaxing"
Morndyke Shepherds' Huts
Luxury Studio Cottage at Foot of Yorkshire Wolds
Studio | Property grounds

Luxury Studio Cottage at Foot of Yorkshire Wolds

3.0 star property
10.0 out of 10, Exceptional, (2)
"This is a lovely place to stay.."
$268 nightly
The price is $321
Sep 2 - Sep 3
Total with taxes and fees
Luxury Studio Cottage at Foot of Yorkshire Wolds
Holtby Grange Cottages
Courtyard

Holtby Grange Cottages

4.0 star property
9.6 out of 10, Exceptional, (7)
"needed a well needed rest after a busy year.After a long search of hotels around york we found this beautiful cottage just outside york,and needless to say it was just what we needed.lovely cottaged estate.we booked the 3 bedroomed cottage,fairview i think it was called.beautiful inside and out.no expense spared on the inside,very relaxing.we are already thinking about booking next year.would highly recommend."
Holtby Grange Cottages
18 Horner Street York
House | Private kitchen

18 Horner Street York

3.0 star property
9.2 out of 10, Wonderful, (9)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
18 Horner Street York
Holiday Cottages and North Star Apartment
Apartment, 1 Bedroom (North Star) | Private kitchen | Fridge, microwave, coffee/tea maker

Holiday Cottages and North Star Apartment

3.5 star property
7.6 out of 10, Good, (9)
"The road to the property is rough and stoney ,Steep metal steps up to apartment , not good with luggage ,Cramped mezanine bedroom with 1 bannister rail missing ,no fire exit instructions ,bathroom has a sloping ceiling and was not good for a tall person. View from kitchen window of old tyre'sand a sink thrown in the I am not sure how this passed any fire and building control regs .Would not return and was not worth the price "
Holiday Cottages and North Star Apartment
The Penthouse
Cottage | 2 bedrooms, individually decorated, individually furnished, free WiFi

The Penthouse

3.0 star property
$580 nightly
The price is $695
Sep 26 - Sep 27
Total with taxes and fees
The Penthouse
Welbury Studio Retreat
Studio | Outdoor dining

Welbury Studio Retreat

3.0 star property
9.0 out of 10, Wonderful, (2)
"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."
$80 nightly
The price is $97
Sep 2 - Sep 3
Total with taxes and fees
Welbury Studio Retreat
Church House Farm
Cottage, Private Bathroom (Bluebell - 3 bedrooms) | Garden

Church House Farm

4.0 star property
10.0 out of 10, Exceptional, (94)
"Absolutely amazing. Wish we could have stayed longer. Accommodations were perfect with a lot of little extras and Rachel, our was very pleasant and extremely helpful. "
Church House Farm
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
7 bedrooms, iron/ironing board, travel crib, free WiFi

Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

9.8 out of 10, Exceptional, (29)
"We had a fantastic time at this property! The owners were incredibly helpful and the facilities and location were superb. Would highly recommend for a large group looking for a fun country escape!"
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
Willow Cottage 4 bedroom Cosy stopover, dogs welcome
Exterior

Willow Cottage 4 bedroom Cosy stopover, dogs welcome

10.0 out of 10, Exceptional, (4)
"A most comfortable bungalow in a delightful village. Host kind & welcoming & the bungalow is kept to a good standard. Recommend the Crosby Inn for a meal too. "
$287 nightly
The price is $287
Sep 1 - Sep 2
Total with taxes and fees
Willow Cottage 4 bedroom Cosy stopover, dogs welcome
The Edge. Modern loft apartment in Yorkshire market town.
Smart TV

The Edge. Modern loft apartment in Yorkshire market town.

10.0 out of 10, Exceptional, (42)
"Excellent accommodation and the hosts were very helpful throughout. Would definitely recommend! "
$170 nightly
The price is $170
Sep 8 - Sep 9
Total with taxes and fees
The Edge. Modern loft apartment in Yorkshire market town.
Craven Garth Cottages
Standard Cottage, 2 Bedrooms (Trevena Star) | Iron/ironing board, free WiFi, bed sheets

Craven Garth Cottages

3.0 star property
9.4 out of 10, Exceptional, (45)
"Phenomenal experience from arriving to going home, nothing was to much to ask, the cottage and amenities are amazing, we got engaged here and it was the perfect setting for it."
Craven Garth Cottages
Middlehead Cottages at Cropton Forest
BBQ/picnic area

Middlehead Cottages at Cropton Forest

3.0 star property
10.0 out of 10, Exceptional, (35)
"Lovely cottage which was well equipped for two very young children. Fantastic scenery all around and the hot tub at night is an absolute bonus! "
Middlehead Cottages at Cropton Forest
Middlehead Huts at Cropton Forest
Front of property

Middlehead Huts at Cropton Forest

3.0 star property
10.0 out of 10, Exceptional, (9)
"We had a lovely time thank you "
Middlehead Huts at Cropton Forest
The Gables
Cottage | Interior

The Gables

3.5 star property
$578 nightly
The price is $694
Sep 3 - Sep 4
Total with taxes and fees
The Gables
Stone-built Cottage In A Tranquil Setting With Views Over Rosedale
Beach

Stone-built Cottage In A Tranquil Setting With Views Over Rosedale

9.8 out of 10, Exceptional, (131)
"Been a few times now. We enjoy visiting evertime . The house is really nice and the area is a delight to visit. Will definitely be visiting again."
Stone-built Cottage In A Tranquil Setting With Views Over Rosedale
Courtyard Rooms - Studio - Double Bed - Wifi
Studio | Dining

Courtyard Rooms - Studio - Double Bed - Wifi

3.0 star property
8.0 out of 10, Very Good, (2)
"Very friendly reception from the landlord Gareth who provided a most enlivening atmosphere in the Duke of Wellington ie a darts match for the men and Easter wreath making for the ladies. No food unfortunately but we found an excellent Italian restaurant in nearby Northallerton. The courtyard room was clean and comfortable, marred only by a very awkward shower - not easy to enter, due to lack of space."
$96 nightly
The price is $96
Sep 4 - Sep 5
Total with taxes and fees
Courtyard Rooms - Studio - Double Bed - Wifi
Wellington Studio Retreat in Northallerton
Studio | Outdoor dining

Wellington Studio Retreat in Northallerton

3.0 star property
$80 nightly
The price is $97
Sep 2 - Sep 3
Total with taxes and fees
Wellington Studio Retreat in Northallerton
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

Find out more about Helmsley

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 $94 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

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 close to well known local attractions in Helmsley, or you can select a secluded option if you want a relaxing place to stay. 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?

18 Horner Street York: You might want to consider this vacation home rental near Helmsley, which has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Helmsley is Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly, .

How many vacation rentals will I find in Helmsley?

With 4 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.