Helmsley Holiday Homes from £60: Search Holiday Homes in Helmsley

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

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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

Helmsley

Helen H.

includes taxes & fees

30 Sept - 1 Oct

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

KIRBYMOORSIDE

A spacious loft with a high ceiling, exposed wooden beams, a kitchen area, and a staircase leading to an upper level.

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

Glaisdale

Catherine C.

includes taxes & fees

15 Oct - 16 Oct

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.

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

Holgate

David H.

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a large bed, a desk, a chair, and a wardrobe.

5. Boutique Barn Secure Parking between York &Harrogate

York, North Yorkshire

Sarah

A brick building with a white door and windows, a small garden area, and a paved driveway.

6. Dove Cottage - Hot Tub, sleeps 2

York

includes taxes & fees

27 Sept - 28 Sept

A hot tub on a wooden deck with stone walls and a tiled roof in the background.

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

Pickering

Deborah H.

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, a television, a window, and a door leading to a bathroom.

8. 2 Bedroom House with Garden next to the River Tees

Stockton on Tees

David R.

includes taxes & fees

27 Sept - 28 Sept

A stone building with a white door, two windows with white frames, and a tiled roof.

9. Daisy Cottage - an enchanting cottage

Scarborough

includes taxes & fees

29 Sept - 30 Sept

A modern kitchen with grey cabinets, a built-in oven, and a sink.

10. The Great Ayton Hideaway

Great Ayton

Nick L.

includes taxes & fees

11 Oct - 12 Oct

A modern living room with a blue sofa, a dining area with a wooden table, and a kitchen with dark cabinets and pendant lighting.

11. Lockwood Cottage, Close to Monk Bar, sleeps 4

The Groves

Nick P.

includes taxes & fees

27 Sept - 28 Sept

A modern kitchen with white cabinetry, a gas stove, and a view into a dining area with a table and chairs.

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

Holgate

A wooden pergola structure with a hot tub and seating area.

13. Host & Stay | Finch House

Stokesley

"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"

jeanette w.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with white cabinetry, a double oven, a sink, and a window with blinds.

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

Rainton

Emily B.

includes taxes & fees

19 Oct - 20 Oct

A living room with a beige sofa, a white rug, a chandelier, a mirror, and a framed picture of the Colosseum.

15. Home and Away

Eaglescliffe

includes taxes & fees

26 Sept - 27 Sept

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

Holgate

John

includes taxes & fees

2 Oct - 3 Oct

A stone house with a red-tiled roof, two visible windows, and a chimney.

17. Manor Cottage

Pickering

includes taxes & fees

6 Oct - 7 Oct

A modern living room with a glass coffee table, a grey sofa, and a decorative clock on the wall.

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

Middlesbrough

Marek

includes taxes & fees

27 Sept - 28 Sept

A narrow hallway with a blue door and patterned floor tiles.

19. Vas's York House

Clifton

Joshua

includes taxes & fees

27 Sept - 28 Sept

A modern wooden structure with a curved roof and large glass windows, surrounded by a wooden deck and metal railings.

20. Wonderful villa for 5 people with WIFI and terrace

Bugthorpe

includes taxes & fees

8 Oct - 9 Oct

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Top Helmsley Hotel Reviews

DoubleTree by Hilton York

8/10 Good

"Parking not enough spaces at hotel charges were too expensive £25 per day stayed Friday 18:00 until 09:00 Sunday charged £50 not happy"

Hotel Clementine

8/10 Good

"Le personnel est très accueillant et attentionné. La propriété ainsi que l'intérieur est très propre. J'ai été un peu déçue car je n'ai pu avoir la chambre spécifique que j'avais réservée car il y avait un problème avec la douche. On m'a offert une autre chambre mais il n'y avait pas de fenêtre. Il faisait donc chaud. Le déjeuner était correct mais petite portion."

Mercure York Fairfield Manor Hotel

10/10 Excellent

"It's true it is a bit dated if that worries you, certainly didn't worry me, perfectly functional very clean, the only thing that bugged me was the Ruddy lift, second floor going down aagh first floor going up that voice done my head in I'm joking of course great location loads of parking, great staff, I'd stay here again."

Impossible Motel

8/10 Good

"My wife and I stayed in a suite on the second floor with a stand alone bathtub. The bath was a great feature but for the opulence of the room you'd expect a bigger sink (One of the tiny rectangular ones) not really in keeping with the standard and price. The bed was extremely big and comfortable, one of the best hotel beds we've stayed in. Location was extremely central but outside noise could be an issue for some (they do provide earplugs) The wifi was poor but that was a minor complaint. Overall it's an interesting place to stay for a night but it's overpriced for what it is."

Find out more about Helmsley

Helmsley Holiday Homes information

Number of reviews	90
Accommodation	808 Holiday Homes
Lowest Price	£60
Highest Price	£1,997

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Helmsley Holiday Rentals

Things to do in Thirsk

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Helmsley holiday homes

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

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

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

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

5. Boutique Barn Secure Parking between York &Harrogate

6. Dove Cottage - Hot Tub, sleeps 2

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

8. 2 Bedroom House with Garden next to the River Tees

9. Daisy Cottage - an enchanting cottage

10. The Great Ayton Hideaway

11. Lockwood Cottage, Close to Monk Bar, sleeps 4

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

13. Host & Stay | Finch House

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

15. Home and Away

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

17. Manor Cottage

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

19. Vas's York House

20. Wonderful villa for 5 people with WIFI and terrace

Find holiday rentals that suit your style

Top Helmsley Hotel Reviews

DoubleTree by Hilton York

Moxy York

Hotel Clementine

The Minster Hotel York

Mercure York Fairfield Manor Hotel

The Feathers Hotel, Helmsley, North Yorkshire

Impossible Motel

The Crown Hotel, Boroughbridge, North Yorkshire

Find out more about Helmsley

Helmsley Holiday Homes information

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