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

Holiday Homes in Helmsley

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Helmsley holiday homes

Smart TV, offices

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

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is NZ$892
includes taxes & fees
29 Sept - 30 Sept
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, (44 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 NZ$911
includes taxes & fees
5 Oct - 6 Oct
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
TV, fireplace

4. 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, (15 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 NZ$293
includes taxes & fees
28 Sept - 29 Sept
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Exterior

5. Daisy Cottage - an enchanting cottage

Daisy Cottage - an enchanting cottage
Scarborough
The price is NZ$285
includes taxes & fees
28 Sept - 29 Sept
Daisy Cottage - an enchanting cottage
Fridge, microwave, oven, stovetop

6. 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 NZ$306
includes taxes & fees
30 Sept - 1 Oct
The Great Ayton Hideaway
TV, offices

7. Dove Cottage - Hot Tub, sleeps 2

Dove Cottage - Hot Tub, sleeps 2
York
The price is NZ$693
includes taxes & fees
16 Sept - 17 Sept
Dove Cottage - Hot Tub, sleeps 2
A heated pool

8. 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 NZ$4,666
includes taxes & fees
16 Sept - 17 Sept
The Grange | sleeps 12 - All Ensuite, Swim Spa, Games Room, Dog Friendly - 5* Gold Award
Smart TV

9. Home and Away

Home and Away
Eaglescliffe
The price is NZ$290
includes taxes & fees
16 Sept - 17 Sept
Home and Away
Interior

10. 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 NZ$401
includes taxes & fees
25 Sept - 26 Sept
Garden Gazebo. Free Parking. 20 mins walk to City and train station.
Smart TV

11. 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 NZ$297
includes taxes & fees
21 Sept - 22 Sept
Entire house 🏠. suitable for families and workers.
Microwave, oven

12. 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 NZ$451
includes taxes & fees
20 Sept - 21 Sept
Beautifully Refurbished Terrace – Just a 15-Minute Riverside Walk into York
Exterior

13. 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 NZ$152
includes taxes & fees
20 Sept - 21 Sept
Vas's York House
Microwave, oven, stovetop, dishwasher

14. 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 NZ$508
includes taxes & fees
7 Oct - 8 Oct
Modern 4-bed home near Thirsk| Ideal for Groups, Families & Work Stays
2 bedrooms, desk, iron/ironing board, free WiFi

15. Portman House

Portman House
Middlesbrough
The price is NZ$212
includes taxes & fees
28 Sept - 29 Sept
Portman House
TV, offices

16. Walpole Retreat - Hot Tub, Games Room, Sleeps 4

Walpole Retreat - Hot Tub, Games Room, Sleeps 4
The Groves
The price is NZ$600
includes taxes & fees
29 Sept - 30 Sept
Walpole Retreat - Hot Tub, Games Room, Sleeps 4
Terrace/patio

17. 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 NZ$1,035
includes taxes & fees
20 Sept - 21 Sept
Host & Stay | Finch House
Dining

18. The Dodsworth modern 4 bedroom house, sleeps 8

The Dodsworth modern 4 bedroom house, sleeps 8
York
9.0 out of 10, Wonderful, (2 reviews)
"Enjoyed our stay in this beautifully decorated, comfortable & clean house. Great location for getting into the city centre, ideal for our weekend break in the run-up to Christmas"
United Kingdom
Rachel G.
The price is NZ$703
includes taxes & fees
17 Sept - 18 Sept
The Dodsworth modern 4 bedroom house, sleeps 8
Cottage | Interior

19. Manor Cottage

Manor Cottage
4.0 star property
Pickering
The price is NZ$1,053
includes taxes & fees
6 Oct - 7 Oct
Manor 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Helmsley Hotel Reviews

Mercure York Fairfield Manor Hotel

Mercure York Fairfield Manor Hotel

10/10 Excellent
"Everything and everyone were and is always is very helpful, pleasant. So much so we have booked for our anniversary."
Rennie 1-night trip
Posted 3 hours ago
Mercure York Fairfield Manor Hotel

Find out more about Helmsley

Helmsley Holiday Homes information

Number of reviews
80
Accommodation
791 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$4,666