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Compare 155 Vacation Homes in Helmsley with updated reviews, rates, and availability.

Host Stay Park View
Room
Host Stay Park View
2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent in every way possible. Clean warm and beautiful "
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, (110)
"My first thought when we got to the venue was ‘oh wow this is beyond what I expected!’ I was blown away at the beauty of the property and surroundings, the layout and finishing touches of the property make it so homely but still clean & well finished without being crowded. The extra touch of a homemade loaf and a little note was such a treat, everything had been thought of and we thoroughly enjoyed our stay, I will definitely recommend to friends & family. Communication was fantastic and nothing...
Luxury Barn Nr York with sauna, ideal for families, friends up to 8 guests
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, (68)
"Comfortable stay with usual visits to local attractions, shops, walks and restaurants!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,
Styfel Cottage Stillington perfect village location with off-street parking ❤️ ❤️
Exterior
Styfel Cottage Stillington perfect village location with off-street parking ❤️ ❤️
10.0 out of 10, Exceptional, (6)
"Stayed for a work in Styfel cottage and it had everything we needed. The place was spotless and very well appointed. Area was fabulous and Stillington was a great location. Highly recommend the Bay Tree Inn for food and drink. Sharon was a great host and even mailed a set a headphones we accidently left behind. Great service!"
Styfel Cottage Stillington perfect village location with off-street parking ❤️ ❤️
Host Stay Fawcett Cottage
Room
Host Stay Fawcett Cottage
Host Stay Fawcett Cottage
Host Stay Grange Cottage
Room
Host Stay Grange Cottage
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, (160)
"In a rural setting, very quiet except when tractors rolling (not often nearby), but 10 minutes from main road networks to very nice towns. Very quiet and peaceful. Well thought out and useable amenities"
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, (49)
"Lovely spacious property. The surroundings are so peaceful. We loved having the horses all around. The croquet and the swimming pool were great and so good to have them on site. Really close to York and lots of things to do. The hosts were very quick to answer questions, show us where we could play football and cricket and provide us with things we needed for the house. Overall very happy with our experience "
Spacious period property on historic, private estate with seasonal, outdoor pool
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, (78)
"The cottage was cozy and unique plus the back garden was a beautiful addition! Definitely recommend it! Malek "
The price is SAR 850
SAR 955 total
includes taxes & fees
24 Sep - 25 Sep
Cottage in village location with lovely views to the Hambleton Hills and White H
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, (31)
"Postgate was perfect and the hosts are fantastic. If you are looking for a beautiful quiet retreat in the country this is the place."
The price is SAR 560
SAR 1,770 total
includes taxes & fees
1 Oct - 2 Oct
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)
"A very handy location with easy on-street parking right in front of the house. Well-equipped kitchen with complimentary, quality coffee and tea. Clean, up-to-date bathroom and towels with quality complimentary shampoo and shower gels. Comfortable master bedroom (as in photo) with good quality mattress, though the other two bedrooms had much lower beds which had less comfortable mattresses. Overall, accommodation was fine for a family of four, though there was no wardrobe hanging space available...
The price is SAR 956
SAR 1,116 total
includes taxes & fees
24 Sep - 25 Sep
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, (18)
"Absolutely amazing stay in the Garden House. The photos don't do it justice, a great space for relaxing, catching up with friends and partying. We were a group of 8, and having separate beds with all bedrooms with ensuite was ideal. There is a fabulous terrace but also access to the pool, tennis and croquet lawn as well as lovely walks from the front door. We had planned to go into York on the evening, but decided to stay at the house, as it was so lovely. We left feeling that the place had...
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.
Property grounds
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"
Maple House - Quaint Victorian Home - Free Parking
Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi
Exterior
Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi
9.6 out of 10, Exceptional, (7)
"Stayed here as a family of 4 for a week in December (grown up kids). We found Jasmine Cottage very well setup and comfortable for our stay, with Angela quick to respond when a few queries for us came up. Local amenities extremely handy, in addition to being a well placed location for trips into York city centre."
Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi
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
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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, (68)
"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 - Grown Up Glamping
Exterior
The Little Hide - Grown Up Glamping
9.2 out of 10, Wonderful, (126)
"We really enjoyed our stay, so peaceful and calming, the trees blowing in the wind around us was a calming lovely sound. Our only issue was the kettle leaking every time you poured a drink and the fitted sheet was not big enough for the bed as soon as got on the bed it came off the mattress when trying to put back on you could get one side down but it pulled it away from other end so bigger fitted sheet and definitely deeper fit other than this it was amazing and just what we needed "
The price is SAR 271
SAR 321 total
includes taxes & fees
13 Oct - 14 Oct
The Little Hide - Grown Up Glamping
The Edge. Modern loft apartment in Yorkshire market town.
Accommodation is where rooflights can be seen in self contained wing
The Edge. Modern loft apartment in Yorkshire market town.
10.0 out of 10, Exceptional, (32)
"It was very clean, spacious, and modern accommodation with crispy clean beddings and comfortable beds. There was a small but sufficient kitchen with a fridge, hobs, all utensils, cookware etc. There was free tea and coffee available, TV, board games. Safe, free parking was helpful. I travel a lot and I have never given 10 out of 10 to any accommodation before, but I am happy to do it now."
The price is SAR 495
SAR 575 total
includes taxes & fees
24 Sep - 25 Sep
The Edge. Modern loft apartment in Yorkshire market town.
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.