Helmsley Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Helmsley vacation rentals

Living area

Ivy Cottage, Helmsley

Ivy Cottage, Helmsley
Helmsley
The price is ￥93,777
￥93,777 total
includes taxes & fees
Apr 23 - Apr 24
Ivy Cottage, Helmsley
Smart TV, offices

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
The price is ￥75,066
￥85,617 total
includes taxes & fees
Apr 16 - Apr 17
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Cottage | Interior

Ivy Cottage

Ivy Cottage
3.5 star property
York
The price is ￥74,560
￥89,472 total
includes taxes & fees
Apr 19 - Apr 20
Ivy Cottage
Living area

8 Pottergate Mews, Helmsley

8 Pottergate Mews, Helmsley
York
The price is ￥178,953
￥178,953 total
includes taxes & fees
May 2 - May 3
8 Pottergate Mews, Helmsley
Cottage | Interior

29 Bondgate

29 Bondgate
3.5 star property
York
The price is ￥90,053
￥108,064 total
includes taxes & fees
Apr 20 - Apr 21
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
The price is ￥92,250
￥110,700 total
includes taxes & fees
Apr 26 - Apr 27
Cliff House
Fridge, electric kettle, toaster, cookware/dishes/utensils

Elm Tree Cottage

Elm Tree Cottage
3.0 star property
Thirsk
10.0 out of 10, Exceptional, (1 review)
"Elm tree cottage was the best stay I’ve had in Yorkshire , I visit often and by far the best place I’ve stayed the hosts were lovely and kind and was great to chat too! The location was perfect in a cute little village on a farm close to Thirsk and an easy drive to York. Providing the essentials for cooking and a cozy little cottage too! Would definitely recommend and look forward to returning in the future! "
United Kingdom
Kira
The price is ￥59,853
￥71,824 total
includes taxes & fees
Apr 18 - Apr 19
Elm Tree Cottage
Premium bedding, individually decorated, individually furnished

Morndyke Shepherds' Huts

Morndyke Shepherds' Huts
3.5 star property
Thirsk
9.8 out of 10, Exceptional, (20 reviews)
"Lovely place to stay, very relaxing"
United Kingdom
John
The price is ￥25,571
￥30,685 total
includes taxes & fees
Apr 16 - Apr 17
Morndyke Shepherds' Huts
Living area

Pheasant Cottage, Danby

Pheasant Cottage, Danby
Whitby
The price is ￥92,394
￥92,394 total
includes taxes & fees
Apr 28 - Apr 29
Pheasant Cottage, Danby
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)
"The property exceeded what we were expecting. Very clean, fully equipped with kitchen cutlery, plates, cups etc. Cannot fault the property, area, or hospitality shown by the owners. We are looking forward to booking again, this time for a little longer. "
United Kingdom
Tara
The price is ￥38,209
￥38,209 total
includes taxes & fees
Apr 26 - Apr 27
Ensuite Family Cabin with Private Hot Tub
Living area

Westonby Lodge, Lealholm

Westonby Lodge, Lealholm
Whitby
The price is ￥190,944
￥190,944 total
includes taxes & fees
Apr 17 - Apr 18
Westonby Lodge, Lealholm
Living area

Woodend, Loftus, North Yorkshire

Woodend, Loftus, North Yorkshire
Saltburn-by-the-Sea
The price is ￥124,191
￥124,191 total
includes taxes & fees
Apr 17 - Apr 18
Woodend, Loftus, North Yorkshire
Living area

Charming Street House Cottage Retreat

Charming Street House Cottage Retreat
Saltburn-by-the-Sea
The price is ￥97,002
￥97,002 total
includes taxes & fees
Apr 17 - Apr 18
Charming Street House Cottage Retreat
Room

Harrington Cottage, Marske-By-The-Sea

Harrington Cottage, Marske-By-The-Sea
Redcar
The price is ￥101,841
￥101,841 total
includes taxes & fees
Apr 20 - Apr 21
Harrington Cottage, Marske-By-The-Sea
Living area

Wayside Cottage, Pickering

Wayside Cottage, Pickering
Pickering
The price is ￥94,007
￥94,007 total
includes taxes & fees
Apr 17 - Apr 18
Wayside Cottage, Pickering
Living area

Meadow Cottage on Working Farm

Meadow Cottage on Working Farm
York
The price is ￥95,159
￥95,159 total
includes taxes & fees
Apr 18 - Apr 19
Meadow Cottage on Working Farm
Interior

Dragonstone Lodge

Dragonstone Lodge
3.0 star property
Northallerton
10.0 out of 10, Exceptional, (1 review)
"We loved this property. The owners obviously have an eye for decor as it is a really stylish place and beautifully finished. We loved how peaceful the property was and the owners had thought of everything . We really appreciated the tea, coffee and milk after a 5 hour drive and the muffins, biscuits and crisps were a lovely touch. All the information you needed was in a folder and we visited lots of the places recommenced in it. It’s a fantastic property and we hope to stay there again."
United Kingdom
Mark
The price is ￥48,687
￥58,424 total
includes taxes & fees
Apr 18 - Apr 19
Dragonstone Lodge
Studio | Dining

Welbury Studio Retreat

Welbury Studio Retreat
3.0 star property
Northallerton
9.0 out of 10, Wonderful, (2 reviews)
"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 ￥11,359
￥13,631 total
includes taxes & fees
Apr 19 - Apr 20
Welbury Studio Retreat
Room

Old Joiners Shop, Staithes

Old Joiners Shop, Staithes
Saltburn-by-the-Sea
The price is ￥83,408
￥83,408 total
includes taxes & fees
Apr 17 - Apr 18
Old Joiners Shop, Staithes
Room

Cornfield Lodge, Northallerton

Cornfield Lodge, Northallerton
Northallerton
The price is ￥128,108
￥128,108 total
includes taxes & fees
Apr 27 - Apr 28
Cornfield Lodge, 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

DoubleTree by Hilton York

DoubleTree by Hilton York

2/10 Terrible
"Room was very dated with broken furniture and dirty windows "
paul 2-night trip
Posted 7 hours ago
DoubleTree by Hilton York

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia! 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
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  • 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 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 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 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.