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Helmsley Holiday Rentals

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Holiday Rentals in Helmsley

Ivy Cottage
3.5 star property
The price is AU$817
includes taxes & fees
3 Nov - 4 Nov
Ivy Cottage
Cliff House
3.5 star property
The price is AU$1,010
includes taxes & fees
21 Nov - 22 Nov
Cliff House
29 Bondgate
3.5 star property
The price is AU$994
includes taxes & fees
28 Oct - 29 Oct
29 Bondgate
The Little Hide - Adult Only Camping Pods
2.0 star property
9.2 out of 10, Wonderful, (147)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
United Kingdom
Michael
The price is AU$123
includes taxes & fees
26 Oct - 27 Oct
The Little Hide - Adult Only Camping Pods
Morndyke Shepherds' Huts
3.5 star property
9.8 out of 10, Exceptional, (19)
"Amazing place, thanks so much ! "
United Kingdom
Tom
Morndyke Shepherds' Huts
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.."
United Kingdom
Darren
The price is AU$507
includes taxes & fees
30 Oct - 31 Oct
Luxury Studio Cottage at Foot of Yorkshire Wolds
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 "
Australia
Christina
18 Horner Street York
Keep Cottage
3.5 star property
10.0 out of 10, Exceptional, (2)
"We had a great stay at Keep Cottage. The cottage is in a perfect position for exploring Pickering but at the same in a lovely quiet location a stones throw from the old castle. Parking was on the street but never a problem. The cottage was warm, cosy and well equipped. We would definitely stay again."
United Kingdom
Angus
Keep Cottage
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."
United Kingdom
Gillian
The price is AU$156
includes taxes & fees
23 Oct - 24 Oct
Welbury Studio Retreat
The Stables, Crayke Lodge
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is AU$574
includes taxes & fees
25 Oct - 26 Oct
The Stables, Crayke Lodge
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."
United Kingdom
Alison
The price is AU$153
includes taxes & fees
24 Oct - 25 Oct
Courtyard Rooms - Studio - Double Bed - Wifi
Croft Granary
2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a really good stay. The cottage is beautiful and equipped with absolutely everything you could ever need. Our son really enjoyed the garden, in particular the Wendy House which was also kitted out with toys, which was a lovely bonus. The village is peaceful but perfect for a nice walk. We would thoroughly recommend the property and would stay again. "
United Kingdom
Leslie
The price is AU$631
includes taxes & fees
2 Nov - 3 Nov
Croft Granary
Wellington Studio Retreat in Northallerton
3.0 star property
The price is AU$153
includes taxes & fees
23 Oct - 24 Oct
Wellington Studio Retreat in Northallerton
Lanes Barn
2.0 star property
10.0 out of 10, Exceptional, (1)
"Tardis like quality of feeling a lot bigger than it looks from the outside. Very clean and homely. Made to feel very welcome. The animals in the nearby fields are great to watch. The village is tiny noticed two shops, the butchers and a general store but all this added to the feeling of calmness. The accommodation was just far enough away from Whitby but close enough to not be a burden. Unless you’re a serious walker you will need to use the car. The nearest pub, The Board Inn, is a short...
United Kingdom
Mike
The price is AU$804
includes taxes & fees
14 Nov - 15 Nov
Lanes Barn
5 Church View
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is AU$675
includes taxes & fees
2 Nov - 3 Nov
5 Church View
The Old Dairy
3.0 star property
10.0 out of 10, Exceptional, (1)
"Good experience "
United States
Todd
The price is AU$823
includes taxes & fees
29 Oct - 30 Oct
The Old Dairy
Brook Cottage
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely very very clean lovely owners and very helpful brilliant location and views "
United Kingdom
Laine
The price is AU$897
includes taxes & fees
7 Nov - 8 Nov
Brook Cottage
Chapel Cottage
2.0 star property
9.4 out of 10, Exceptional, (3)
"The property was beautiful and the owner, David, was very welcoming."
United Kingdom
Geraldine
The price is AU$864
includes taxes & fees
27 Oct - 28 Oct
Chapel Cottage
Hogwarts Cottage
3.0 star property
8.0 out of 10, Very good, (2)
"Only concern was parking.apart from thatvspot on"
United Kingdom
Paul
The price is AU$609
includes taxes & fees
7 Nov - 8 Nov
Hogwarts Cottage
Owl's Nest
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is AU$736
includes taxes & fees
25 Oct - 26 Oct
Owl's Nest
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

Everything you need to know about Helmsley holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Helmsley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Helmsley holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Helmsley holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Helmsley holiday rentals we have selected for you start as low as AU$123 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Helmsley rentals

At Expedia, we put the best Helmsley holiday 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 holiday.

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 holiday rentals in Helmsley?

Yes, there are holiday rentals close to the most popular sights in Helmsley, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Helmsley has to offer?

18 Horner Street York: This holiday home rental outside of Helmsley has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Helmsley?

With 4 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Helmsley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Helmsley. Holiday rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.