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Compare 158 Vacation Homes in Helmsley with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (80)
"We chose this property because it's location allowed easy reach of York, Harrogate and sightseeing opportunities towards the North Yorks Moors. Lovely house in a quiet village. Generous rooms, great facilities. We were late in the season so didn't get a chance to use the outdoors areas but would be great in the summer. No issues, but where we had questions/requests the host responded almost immediately and came round if necessary. Highly recommended"
The price is SAR 753
SAR 851 total
includes taxes & fees
22 Dec - 23 Dec
Cottage in village location with lovely views to the Hambleton Hills and White H
Host Stay Park View
Room

Host Stay Park View

2.0 star property
8.0 out of 10, Very Good, (3)
"After been there twice the communication is poor both times I questioned if there was an iron and nothing so I had to buy one "
Host Stay Park View
Luxury Barn Nr York with sauna, ideal for families, friends up to 8 guests
View of Barn from our Paddocks

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

10.0 out of 10, Exceptional, (111)
"Beautiful place, and location"
Luxury Barn Nr York with sauna, ideal for families, friends up to 8 guests
Host Stay Fawcett Cottage
Room

Host Stay Fawcett Cottage

3.0 star property
Host Stay Fawcett Cottage
Host Stay Grange Cottage
Room

Host Stay Grange Cottage

2.0 star property
Host Stay Grange Cottage
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
The Red Barn rear view

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

9.8 out of 10, Exceptional, (26)
"The farmhouses were lovely, and our stay there was great. Thank you!!!"
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
Rural, peaceful, beautifully done barn for 2, stunning farm views, woodburner
Sitting room- everything is brand new in June 2016

Rural, peaceful, beautifully done barn for 2, stunning farm views, woodburner

10.0 out of 10, Exceptional, (161)
"Lovely cottage, well appointed. Good base for lots of day trips. "
Rural, peaceful, beautifully done barn for 2, stunning farm views, woodburner
Spacious period property on historic, private estate with seasonal, outdoor pool
West Wing of historic Manor House

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

10.0 out of 10, Exceptional, (50)
"A wonderful weekend, the perfect house, spacious, well equipped, spotless, and a lovely welcome basket of goodies and a birthday balloon-so thoughtful. Perfectly situated for a quiet weekend and easy access to York and local tourist spots. We had a lovely time, thank you."
Spacious period property on historic, private estate with seasonal, outdoor pool
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Exterior

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

10.0 out of 10, Exceptional, (32)
"Loved the location and the property was lovely. We would return again!"
The price is SAR 494
SAR 1,628 total
includes taxes & fees
27 Nov - 28 Nov
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
18 Horner Street York
Room

18 Horner Street York

3.0 star property
9.2 out of 10, Wonderful, (9)
"Last minute booking as decided to stay overnight in York. Communication for check in was quick, property was easy to find, close to town and super clean and tidy. Had a relaxing stay and would definitely consider again next time we were in York. Small supermarket and Mrs Greedy’s at end of road was excellent for supplies and a quick cooked breakfast. "
The price is SAR 900
SAR 1,050 total
includes taxes & fees
25 Nov - 26 Nov
18 Horner Street York
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool
The spacious living area

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

10.0 out of 10, Exceptional, (20)
"Such a historic venue, so peaceful if a bit remote. 5-10 minutes to get to the main road. Easy to find though, postcode satnav takes you right to the property with well signed directions when there. The property and grounds were immaculate, added bonus of an outside plug at parking to trickle charge an electric vehicle. "
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool
Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI
Beautiful 18th Century Listed Stone Cottage front garden.

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

10.0 out of 10, Exceptional, (20)
"Perfect for a couple's stay. Nicely furnished and well equipped. Nice village location with 2 pubs and a chippy. 20 mins drive to Castle Howard."
Gorgeous Thornton-le-Dale 2 Bedroom Cottage & Garden, Cosy Family Friendly, WIFI
New 2021. A well presented holiday home with one double and one twin.
Holiday Home 2 - Cleveland Hills View, Hutton Rudby, Yarm

New 2021. A well presented holiday home with one double and one twin.

10.0 out of 10, Exceptional, (1)
New 2021. A well presented holiday home with one double and one twin.
Maple House - Quaint Victorian Home - Free Parking
Living room, featuring a fireplace and smart tv.

Maple House - Quaint Victorian Home - Free Parking

9.0 out of 10, Wonderful, (2)
"Smaller downstairs than upstairs but the bathroom was nice and bedrooms large enough. However as in York for family funeral and only needed somewhere to sleep, location and facilites were not a real factor, sorry. Pity about the streetlight outside the bedroom window though"
The price is SAR 1,176
SAR 1,482 total
includes taxes & fees
22 Dec - 23 Dec
Maple House - Quaint Victorian Home - Free Parking
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
Feversham Cottages 1 and 2 Stonegarth

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

10.0 out of 10, Exceptional, (70)
"This was just perfect! The house was well stocked including the kitchen and the location could not have been better. It was so lovely just to walk through the church yard to the pub for dinner. I would highly recommend and we will def. be back!!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
High Oaks Grange | The Grange

The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award

10.0 out of 10, Exceptional, (3)
"High Oaks Grange is a beautiful property with a very high standard of fittings. We had everything we needed for a wonderful stay with old friends. There were plenty of things to do locally and we loved the area. One highlight was a meal cooked for us in the Grange by Chef Dan Graham. We would thoroughly recommend him. as would we would highly recommend The Grange for a large group. We hope to return in the future."
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Studio room that sleeps 2 guests in 1 bedroom, short breaks all year round
Room

Studio room that sleeps 2 guests in 1 bedroom, short breaks all year round

10.0 out of 10, Exceptional, (2)
"As above"
Studio room that sleeps 2 guests in 1 bedroom, short breaks all year round
Private Bungalow ? Cottage in private courtyard
Exterior

Private Bungalow ? Cottage in private courtyard

Private Bungalow ? Cottage in private courtyard
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

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

10.0 out of 10, Exceptional, (7)
"Gorgeous barb conversion. Not far from Whitby. View is amazing. Emma and Chris are lovely with a beautiful family. Recommended to friends who are going to book. Thank you for having us"
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast
Luxurious, comfortable converted barn in North Yorkshire near York and Malton
Living area

Luxurious, comfortable converted barn in North Yorkshire near York and Malton

10.0 out of 10, Exceptional, (7)
"as advertised, comfortable and well equipped. Lovely quiet setting. As it's a rural location, there are lots of flies! Not unexpected of course - would recommend some kind of fly killer machine would be helpful. Overall, lovely place and would certainly recommend."
Luxurious, comfortable converted barn in North Yorkshire near York and Malton
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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Other property types in Helmsley

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
Feversham Cottages 1 and 2 Stonegarth

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

10.0 out of 10, Exceptional, (70)
"This was just perfect! The house was well stocked including the kitchen and the location could not have been better. It was so lovely just to walk through the church yard to the pub for dinner. I would highly recommend and we will def. be back!!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
The Little Hide - Grown Up Glamping
Exterior

The Little Hide - Grown Up Glamping

2.0 star property
9.2 out of 10, Wonderful, (128)
"Lovely, clean cosy pod. Helpful staff, lovely location"
The price is SAR 247
SAR 294 total
includes taxes & fees
22 Dec - 23 Dec
The Little Hide - Grown Up Glamping
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
The Red Barn rear view

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

9.8 out of 10, Exceptional, (26)
"The farmhouses were lovely, and our stay there was great. Thank you!!!"
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.
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.