Photo by Ron Jnr

Helmsley Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Vacation Rentals in Helmsley

Private kitchen
29 Bondgate
29 Bondgate
3.5 star property
The price is RM2,284
RM2,740 total
includes taxes & fees
28 Oct - 29 Oct
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cliff House
Cliff House
3.5 star property
Cliff House
Interior
Ivy Cottage
Ivy Cottage
3.5 star property
The price is RM1,877
RM2,252 total
includes taxes & fees
2 Nov - 3 Nov
Ivy Cottage
Property grounds
Luxury Studio Cottage at Foot of Yorkshire Wolds
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 RM1,007
RM1,481 total
includes taxes & fees
22 Oct - 23 Oct
Luxury Studio Cottage at Foot of Yorkshire Wolds
Terrace/patio
The Old Granary - Holiday Cottage
The Old Granary - Holiday Cottage
4.0 star property
9.4 out of 10, Exceptional, (3)
"We really enjoyed our stay here, the property was well equipped with everything you needed for a comfortable stay. I do think the property does need updating a little and it would have been nice if the hot tub had been filled on arrival, the hot tub also needs a cover as unless you like cold feb rain wouldn’t have been enjoyable. "
United Kingdom
lynsey
The price is RM1,023
RM1,228 total
includes taxes & fees
28 Oct - 29 Oct
The Old Granary - Holiday Cottage
Private kitchen
18 Horner Street York
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
Interior
The Stables, Crayke Lodge
The Stables, Crayke Lodge
3.5 star property
10.0 out of 10, Exceptional, (1)
The Stables, Crayke Lodge
Interior
5 Church View
5 Church View
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is RM1,551
RM1,861 total
includes taxes & fees
22 Oct - 23 Oct
5 Church View
Dining
Courtyard Rooms - Studio - Double Bed - Wifi
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 RM449
RM449 total
includes taxes & fees
20 Oct - 21 Oct
Courtyard Rooms - Studio - Double Bed - Wifi
Fridge, dishwasher, electric kettle, toaster
The Old Dairy
The Old Dairy
3.0 star property
10.0 out of 10, Exceptional, (1)
"Good experience "
United States
Todd
The price is RM1,891
RM2,269 total
includes taxes & fees
29 Oct - 30 Oct
The Old Dairy
Outdoor dining
Croft Granary
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 RM1,451
RM1,742 total
includes taxes & fees
1 Nov - 2 Nov
Croft Granary
1 bedroom
The Little Hide - Adult Only Camping Pods
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 RM284
RM340 total
includes taxes & fees
2 Nov - 3 Nov
The Little Hide - Adult Only Camping Pods
Fridge, electric kettle, toaster, cookware/dishes/utensils
Sheep Cote Shepherds Hut
Sheep Cote Shepherds Hut
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very beautiful surroundings, the shepherd’s hut is well situated for travelling around the moors. The hut is perfect, very clean and well designed space. It had everything I needed and more "
United Kingdom
Jennifer
The price is RM1,872
RM2,247 total
includes taxes & fees
22 Oct - 23 Oct
Sheep Cote Shepherds Hut
Garden
Auburn House
Auburn House
3.5 star property
10.0 out of 10, Exceptional, (2)
"Lovely house with great facilities- has everything we could have needed to enjoy our stay. Quiet area but easy access to North Yorks Moors and other local attractions. "
United Kingdom
Stephen
The price is RM2,979
RM3,574 total
includes taxes & fees
16 Nov - 17 Nov
Auburn House
Outdoor dining
Welbury Studio Retreat
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 RM374
RM449 total
includes taxes & fees
20 Oct - 21 Oct
Welbury Studio Retreat
Interior
Hogwarts 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 RM1,400
RM1,679 total
includes taxes & fees
7 Nov - 8 Nov
Hogwarts Cottage
Balcony
Beech View
Beech View
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is RM1,324
RM1,589 total
includes taxes & fees
2 Nov - 3 Nov
Beech View
Interior
Cooper's Cottage
Cooper's Cottage
3.5 star property
8.0 out of 10, Very good, (1)
"Smell of sewage in the lounge, no response from message sent to contact number in info folder. Steps to bathroom are lethal."
United Kingdom
ANGELA
The price is RM1,404
RM1,685 total
includes taxes & fees
30 Oct - 31 Oct
Cooper's Cottage
Interior
Lanes Barn
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 RM3,139
RM3,767 total
includes taxes & fees
1 Nov - 2 Nov
Lanes Barn
Fridge, dishwasher, electric kettle, toaster
Temple Hill View
Temple Hill View
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was lovely, spacious, clean and well stocked with anything you might need. It is in a tranquil village and has plentiful off-road parking. The garden has an excellent view and is so peaceful to sit in. There is a park 2 minutes down the lane, a football field, and if you continue down the lane, there is a pond and a lovely walk around it. It was perfectly located between all the walking areas I wanted to see and complete. When we arrived there was bread, milk and some treats waiting...
United Kingdom
Jade
The price is RM2,340
RM2,808 total
includes taxes & fees
30 Oct - 31 Oct
Temple Hill View
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Helmsley Hotel Reviews

Grantham Arms

Grantham Arms

10/10 Excellent
"What a find in a beautiful area. Short trip off the A1 and absolutely stunning pub with rooms. Rooms were great, comfortable clean and has everything you will need for a good stay. Dinner was really tasty. Didn’t stop for breakfast but can only imagine how nice it would be. Would definitely recommend and would stay next time I am in the area "
lee 1-night trip
Posted 1 day ago
Grantham Arms

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Helmsley using one of the methods below:

  • View our selection of featured holiday rentals in Helmsley
  • Use the map to find apartments and other holiday homes in the Helmsley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Helmsley while they last

Look no further and take a look at our great range of rental properties in Helmsley!

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.