A medieval castle surrounded by a lush green landscape and a small village in the background.

Holiday Homes in Helmsley

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Helmsley holiday homes

A cozy living room with a fireplace, a television, and comfortable seating.

1. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
The price is €466
includes taxes & fees
31 Aug - 1 Sept
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A beach with rocks and people walking.

2. WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms

WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms
KIRBYMOORSIDE
WEST END - a holiday cottage that sleeps 9 guests in 5 bedrooms
A modern living room with a black sofa, a glass coffee table, a TV, and a dining area with a small table and four chairs.

3. Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Holgate
8.8 out of 10, Excellent, (14 reviews)
"Everything was as explained.Great location, great communication with the host, the property had everything you would need for a short stay and was exceptionaly clean"
United Kingdom
David H.
The price is €151
includes taxes & fees
1 Sept - 2 Sept
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
A spacious loft with a high ceiling, exposed wooden beams, a kitchen area, and a staircase leading to an upper level.

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

Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Glaisdale
10.0 out of 10, Exceptional, (43 reviews)
"The property was excellent, beautiful throughout. We enjoyed our stay and the hosts were very welcoming and friendly. We would highly recommend "
United Kingdom
Catherine C.
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
A hot tub on a wooden deck with stone walls and a tiled roof in the background.

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

The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Pickering
10.0 out of 10, Exceptional, (3 reviews)
"Eight friends (5 of whom were at uni together in the 70s) meet every year. Yorkshire was this year’s choice. We couldn’t have stayed in a better location. We loved everything: the house; the swim spa; the area; the weather. We would love to come back. Thank you!"
United Kingdom
Deborah H.
The price is €2,330
includes taxes & fees
31 Aug - 1 Sept
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
A stone building with a white door, two windows with white frames, and a tiled roof.

6. Daisy Cottage - an enchanting cottage

Daisy Cottage - an enchanting cottage
Scarborough
The price is €162
includes taxes & fees
31 Aug - 1 Sept
Daisy Cottage - an enchanting cottage
A modern kitchen with grey cabinets, a built-in oven, and a sink.

7. The Great Ayton Hideaway

The Great Ayton Hideaway
Great Ayton
8.0 out of 10, Very good, (1 review)
"Did what it said on the tin"
United Kingdom
Nick L.
The price is €193
includes taxes & fees
24 Sept - 25 Sept
The Great Ayton Hideaway
A modern kitchen with a central island, pendant lights, and a skylight.

8. Contemporary eco home with a twist!

Contemporary eco home with a twist!
Marton-in-Cleveland
The price is €183
includes taxes & fees
29 Aug - 30 Aug
Contemporary eco home with a twist!
A modern kitchen with white cabinetry, a double oven, a sink, and a window with blinds.

9. Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays

Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
Rainton
9.0 out of 10, Wonderful, (2 reviews)
"Family friendly , just as described on the booking, very clean and spacious we had no complaints, we paid 10 for earlier check in which was fantastic thank you!"
United States
Emily B.
The price is €273
includes taxes & fees
22 Sept - 23 Sept
Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
A residential property with a brick exterior, a wooden garage door, a gravel driveway, and a well-maintained garden.

10. 20 Hazelnut Grove · Spacious Contemporary 2-Bed House in York - Pass the Keys

20 Hazelnut Grove · Spacious Contemporary 2-Bed House in York - Pass the Keys
York
20 Hazelnut Grove · Spacious Contemporary 2-Bed House in York - Pass the Keys
A wooden pergola structure with a hot tub and seating area.

11. Host & Stay | Finch House

Host & Stay | Finch House
Stokesley
9.0 out of 10, Wonderful, (2 reviews)
"A perfect stay in a beautiful property. I always say you get what you pay for, so while it seemed expensive when I booked it, it was so worth the money. Everything was spot on, the furnishings were sumptuous, furniture and beds were top quality, bedrooms and bathrooms were luxurious. Host was great and left a lovely welcome hamper with wine, chocolate etc. All in all, I couldn't fault Finch House"
United States
jeanette w.
The price is €557
includes taxes & fees
31 Aug - 1 Sept
Host & Stay | Finch House

12. Westbourne House Horizon Stays

Westbourne House Horizon Stays
2.0 star property
Middlesbrough
The price is €345
includes taxes & fees
1 Sept - 2 Sept
Westbourne House Horizon Stays
A stone house with a red-tiled roof, two visible windows, and a chimney.

13. Manor Cottage

Manor Cottage
4.0 star property
Pickering
The price is €528
includes taxes & fees
5 Sept - 6 Sept
Manor Cottage

14. Garden Gazebo. Free Parking. 20 mins walk to City and train station.

Garden Gazebo. Free Parking. 20 mins walk to City and train station.
Holgate
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely brulliant property.. a home away from home"
United Kingdom
John
The price is €207
includes taxes & fees
31 Aug - 1 Sept
Garden Gazebo. Free Parking. 20 mins walk to City and train station.
A modern kitchen with white cabinetry, a gas stove, and a view into a dining area with a table and chairs.

15. Beautifully Refurbished Terrace – Just a 15-Minute Riverside Walk into York

Beautifully Refurbished Terrace – Just a 15-Minute Riverside Walk into York
Holgate
The price is €230
includes taxes & fees
13 Sept - 14 Sept
Beautifully Refurbished Terrace – Just a 15-Minute Riverside Walk into York
A bedroom with a bed, a television, a window, and a door leading to a bathroom.

16. 2 Bedroom House with Garden next to the River Tees

2 Bedroom House with Garden next to the River Tees
Stockton on Tees
10.0 out of 10, Exceptional, (3 reviews)
"Good location, host was very responsive, property had everything we needed. Good check-in/out process "
United Kingdom
David R.
The price is €107
includes taxes & fees
30 Aug - 31 Aug
2 Bedroom House with Garden next to the River Tees
A modern, arched wooden structure with a large circular window, a wooden deck with logs, and a clear sky.

17. Stunning villa for 5 guests with WIFI and terrace

Stunning villa for 5 guests with WIFI and terrace
Bugthorpe
The price is €358
includes taxes & fees
8 Sept - 9 Sept
Stunning villa for 5 guests with WIFI and terrace
A cozy living room with a sofa, a coffee table, and a fireplace.

18. Idyllic retreat with log burner near Danby Castle

Idyllic retreat with log burner near Danby Castle
Ainthorpe
Idyllic retreat with log burner near Danby Castle
A dining area with a wooden table set for two, a wicker chair, and a view of the kitchen with wooden cabinets and a stainless steel range hood.

19. 55 Heworth Village · Wonderfully Cosy Family Home in York - Pass the Keys

55 Heworth Village · Wonderfully Cosy Family Home in York - Pass the Keys
York
The price is €275
includes taxes & fees
13 Sept - 14 Sept
55 Heworth Village · Wonderfully Cosy Family Home in York - Pass the Keys
A living room with a beige sofa, a white rug, a chandelier, a mirror, and a framed picture of the Colosseum.

20. Home and Away

Home and Away
Eaglescliffe
The price is €149
includes taxes & fees
29 Aug - 30 Aug
Home and Away
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

Burn Hall Hotel

Burn Hall Hotel

10/10 Excellent
"Staff were friendly and very helpful. Breakfast on both mornings was amazing, I liked how you could still order add ons such as poached eggs or porridge, we'd probably go just for the breakfast. Our room was spotless, and the hotel itself was also. I think the only thing for us was, the rooms could have a tiny bit more security as it's still a hotel which had normal lock and keys on each door"
Lorna 2-night trip
Posted 12 hours ago
Burn Hall Hotel

Find out more about Helmsley

Helmsley Holiday Homes information

Number of reviews
58
Accommodation
855 Holiday Homes
Lowest Price
€107
Highest Price
€2,330