Photo by Ron Jnr

Helmsley Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Helmsley

Our top choices for Helmsley vacation rentals

The Little Hide - Adult Only Camping Pods

2.0 star property
9.2 out of 10, Wonderful, (141)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
The price is ¥10,822
¥12,986 total
includes taxes & fees
Aug 31 - Sep 1
The Little Hide - Adult Only Camping Pods

Malton Central Apartments

3.0 star property
8.8 out of 10, Excellent, (30)
"Again, another great stay and would highly recommend"
Malton Central Apartments

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.."
The price is ¥33,583
¥49,858 total
includes taxes & fees
Sep 20 - Sep 21
Luxury Studio Cottage at Foot of Yorkshire Wolds

Church House Farm

4.0 star property
10.0 out of 10, Exceptional, (93)
"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

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

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

Holiday Cottages and North Star Apartment

3.5 star property
7.6 out of 10, Good, (9)
Holiday Cottages and North Star Apartment

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! "
The price is ¥21,907
¥25,093 total
includes taxes & fees
Sep 20 - Sep 21
The Edge. Modern loft apartment in Yorkshire market town.

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."
The price is ¥12,607
¥15,128 total
includes taxes & fees
Sep 2 - Sep 3
Welbury Studio Retreat

The Penthouse

3.0 star property
The price is ¥85,469
¥102,562 total
includes taxes & fees
Sep 19 - Sep 20
The Penthouse

5 Church View

3.5 star property
10.0 out of 10, Exceptional, (1)
The price is ¥54,434
¥65,322 total
includes taxes & fees
Sep 3 - Sep 4
5 Church View

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

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. "
The price is ¥38,834
¥44,211 total
includes taxes & fees
Sep 2 - Sep 3
Willow Cottage 4 bedroom Cosy stopover, dogs welcome

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

Morndyke Shepherds' Huts

3.5 star property
9.8 out of 10, Exceptional, (19)
"Lovely place to stay, very relaxing"
Morndyke Shepherds' Huts

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

9.8 out of 10, Exceptional, (130)
"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

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."
The price is ¥15,651
¥15,651 total
includes taxes & fees
Sep 8 - Sep 9
Courtyard Rooms - Studio - Double Bed - Wifi

Wellington Studio Retreat in Northallerton

3.0 star property
The price is ¥13,042
¥15,650 total
includes taxes & fees
Aug 21 - Aug 22
Wellington Studio Retreat in Northallerton

Providence Court

3.0 star property
The price is ¥61,239
¥73,487 total
includes taxes & fees
Sep 19 - Sep 20
Providence Court

The Green

3.0 star property
The price is ¥117,831
¥141,396 total
includes taxes & fees
Sep 2 - Sep 3
The Green
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Helmsley Hotel Reviews

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.