Photo by Ron Jnr

Search Vacation Homes in Helmsley

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 219 Vacation Homes in Helmsley with updated reviews, rates, and availability.

Cottage in village location with lovely views to the Hambleton Hills and White H

9.8 out of 10, Exceptional, (86)
"The property was lovely, communication was great "
Cottage in village location with lovely views to the Hambleton Hills and White H

Host Stay Park View

2.0 star property
8.0 out of 10, Very Good, (3)
"Excellent in every way possible. Clean warm and beautiful "
Host Stay Park View

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

9.8 out of 10, Exceptional, (29)
"Fabulous properties, comfortable surroundings and excellently stocked with everything you could need. Great walks and only 15 minutes drive into York. Great pub on the corner of the street….enjoyed by all!"
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

10.0 out of 10, Exceptional, (162)
"A very lovely place to stay. Thanks "
Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

Luxury Barn Nr York with Sauna, ideal for families, friends up to 8 guests

10.0 out of 10, Exceptional, (115)
"Beautiful place, and location"
Luxury Barn Nr York with Sauna, ideal for families, friends up to 8 guests

Fern Lea, a cosy bungalow with exceptional country views

9.6 out of 10, Exceptional, (4)
"Fantastic cottage with everything you need. The garden was perfect for relaxing at the end of a long day walking on the moors.Wonderful views from the cottage both front and back.We will def. return and book again"
Fern Lea, a cosy bungalow with exceptional country views

Host Stay Holmlea Cottage

2.0 star property
Host Stay Holmlea Cottage

Host Stay Grange Cottage

2.0 star property
Host Stay Grange Cottage

Spacious period property on historic, private estate with seasonal, outdoor pool

10.0 out of 10, Exceptional, (51)
"We had such a lovely two days celebrating birthdays. The house is beautiful and so are the grounds. We had everything we needed. I have given a good for the area because we could not use the pool. "
Spacious period property on historic, private estate with seasonal, outdoor pool

Luxury retreat for 2 couples/ family in spectacular location in North York Moors

10.0 out of 10, Exceptional, (35)
"Loved the location and the property was lovely. We would return again!"
The price is AEDĀ 726
AEDĀ 1,931 total
includes taxes & fees
27 May - 28 May
Luxury retreat for 2 couples/ family in spectacular location in North York Moors

Host & Stay | Silton Hall

8.4 out of 10, Very Good, (6)
"We loved everything about this property! It was perfect for our large group. The pool was a huge hit. The rooms and bathrooms were brilliant and perfectly stocked with bedding and towels "
Host & Stay | Silton Hall

Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

10.0 out of 10, Exceptional, (7)
"We enjoyed a lot our stay in this "
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

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 "
The price is AEDĀ 1,559
AEDĀ 1,870 total
includes taxes & fees
15 May - 16 May
18 Horner Street York

Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi

9.6 out of 10, Exceptional, (8)
"The beds were comfortable and the place was clean. The location was convenient for taking the bus into town."
Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

10.0 out of 10, Exceptional, (72)
"Comfortable stay with usual visits to local attractions, shops, walks and restaurants!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool

10.0 out of 10, Exceptional, (20)
"Excellent property in a beautiful & peaceful setting. Garden House was very well equipped & very comfortable. Hosts helpful & pleasant . We enjoyed our stay there. "
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool

No. 10 West End Osmotherley

9.6 out of 10, Exceptional, (40)
"Had a very enjoyanle stay."
No. 10 West End Osmotherley

Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI

10.0 out of 10, Exceptional, (20)
"Lovely, clean and tidy property in a good location. Would stay again."
Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI

Upper Helmsley Hall, Upper Helmsley

10.0 out of 10, Exceptional, (2)
"This is an elegant and comfortable country house in a tiny village just outside York. It has two large, elegant sitting rooms and a panelled dining room, perfect for formal dinners. We loved the house, its rambling corridors, comfortable bedrooms and elegant and fascinating objects and furniture. Perfect for a country house weekend."
Upper Helmsley Hall, Upper Helmsley

Host & Stay | Greengate Cottage

9.2 out of 10, Wonderful, (25)
"Super property with all we needed. Comfortable and clean. Domestic essentials were provided, mot the case in many properties, but tea coffee and milk as well as washing up and dish washer kit. One of the prettiest villages in NYNNP with a pub, tea rooms and a great rural museum"
Host & Stay | Greengate Cottage
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.
Don't see what you're looking for?
See all available properties in Helmsley
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Helmsley

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

10.0 out of 10, Exceptional, (72)
"Comfortable stay with usual visits to local attractions, shops, walks and restaurants!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

The Little Hide - Adult Only Camping Pods

2.0 star property
9.2 out of 10, Wonderful, (136)
"We have a fab time "
The price is AEDĀ 260
AEDĀ 312 total
includes taxes & fees
15 May - 16 May
The Little Hide - Adult Only Camping Pods

Middlehead Huts at Cropton Forest

3.0 star property
10.0 out of 10, Exceptional, (6)
"Lovely last minute stay. Hut is furnished to a high standard. Doggies very much welcomed. Would definitely go back. "
Middlehead Huts at Cropton Forest
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.