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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Helmsley holiday homes

Living area

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 AU$753
includes taxes & fees
26 Aug - 27 Aug
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Beach

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
Interior

3. 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.
The price is AU$825
includes taxes & fees
3 Sept - 4 Sept
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Private kitchen

4. 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 AU$336
includes taxes & fees
30 Aug - 31 Aug
The Great Ayton Hideaway
Exterior

5. Daisy Cottage - an enchanting cottage

Daisy Cottage - an enchanting cottage
Scarborough
The price is AU$247
includes taxes & fees
8 Sept - 9 Sept
Daisy Cottage - an enchanting cottage
Living area

6. 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 AU$243
includes taxes & fees
1 Sept - 2 Sept
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Pool

7. 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 AU$3,800
includes taxes & fees
31 Aug - 1 Sept
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Interior

8. 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 AU$333
includes taxes & fees
9 Sept - 10 Sept
Garden Gazebo. Free Parking. 20 mins walk to City and train station.
Living area

9. Home and Away

Home and Away
Eaglescliffe
The price is AU$239
includes taxes & fees
23 Aug - 24 Aug
Home and Away
Private kitchen

10. 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 AU$399
includes taxes & fees
7 Sept - 8 Sept
Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
Room

11. 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 AU$171
includes taxes & fees
31 Aug - 1 Sept
2 Bedroom House with Garden next to the River Tees
Cottage | Interior

12. Manor Cottage

Manor Cottage
4.0 star property
Pickering
The price is AU$862
includes taxes & fees
5 Sept - 6 Sept
Manor Cottage
Private kitchen

13. 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 AU$436
includes taxes & fees
6 Sept - 7 Sept
Beautifully Refurbished Terrace – Just a 15-Minute Riverside Walk into York
Terrace/patio

14. 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 AU$912
includes taxes & fees
27 Aug - 28 Aug
Host & Stay | Finch House
Living area

15. 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
Dining

16. 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
55 Heworth Village · Wonderfully Cosy Family Home in York - Pass the Keys
Living area

17. Entire house 🏠. suitable for families and workers.

Entire house 🏠. suitable for families and workers.
Middlesbrough
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and a good area"
United Kingdom
Marek
The price is AU$241
includes taxes & fees
13 Sept - 14 Sept
Entire house 🏠. suitable for families and workers.
Exterior

18. Vas's York House

Vas's York House
2.0 star property
Clifton
6.8 out of 10, (5 reviews)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
The price is AU$124
includes taxes & fees
8 Sept - 9 Sept
Vas's York House
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

8/10 Good
"The waitress in the dining room greets visitors with morning Guys when morning would be suffice as she can clearly sees some of the visitors are ladies"
Simon 5-night trip
Posted less than an hour ago
Burn Hall Hotel

Find out more about Helmsley

Helmsley Holiday Homes information

Number of reviews
65
Accommodation
795 Holiday Homes
Lowest Price
AU$124
Highest Price
AU$3,800