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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Helmsley cottages

Exterior
29 Bondgate

Cottage in York

29 Bondgate
3.5 star property
The price is AED 2,018
AED 2,421 total
includes taxes & fees
29 Dec - 30 Dec
29 Bondgate
Cottage | Interior
Ivy Cottage

Cottage in York

Ivy Cottage
3.5 star property
The price is AED 1,700
AED 2,040 total
includes taxes & fees
6 Jan - 7 January 2026
Ivy Cottage
Property grounds
Cliff House

Cottage in York

Cliff House
3.5 star property
The price is AED 2,051
AED 2,461 total
includes taxes & fees
29 Dec - 30 Dec
Cliff House
Exterior
Sykes Lodge

Cottage in Malton

Sykes Lodge
3.0 star property
The price is AED 11,988
AED 14,386 total
includes taxes & fees
5 Jan - 6 January 2026
Sykes Lodge
Garden
Craven Garth Cottages

Cottage in Pickering

Craven Garth Cottages
3.0 star property
9.4 out of 10, Exceptional, (46)
"Really nice place,friendly landlord and very helpful"
United Kingdom
Corin
The price is AED 942
AED 1,130 total
includes taxes & fees
10 Jan - 11 January 2026
Craven Garth Cottages
Property grounds
Glendevon Cottage - Enjoy a short 2-night stay

Cottage in Staithes

Glendevon Cottage - Enjoy a short 2-night stay
9.6 out of 10, Exceptional, (159)
"Lovely cottage , clean and fully equipped to meet needs. Lovely, relaxing outdoor seating area . "
United Kingdom
Tracey d.
Glendevon Cottage - Enjoy a short 2-night stay
Exterior
Stoney Nook Cottage

Cottage in Guisborough

Stoney Nook Cottage
9.2 out of 10, Wonderful, (5)
"Beautifully renovated cottage with comfortable bed and modern washroom. Conveniently located for exploring Guisborough and helpful guidebook with suggestions for the kids and adults. The grocery store is a 5-minute block away also. Andy was very helpful and easy to communicate with."
Canada
Shelley & J.
The price is AED 354
AED 432 total
includes taxes & fees
4 Jan - 5 January 2026
Stoney Nook Cottage
Exterior
HAYSTACK COTTAGE SLEEPING 2 NEXT TO FOX COVERT PUB YARM

Cottage in High Leven

HAYSTACK COTTAGE SLEEPING 2 NEXT TO FOX COVERT PUB YARM
9.0 out of 10, Wonderful, (2)
"Enjoyed our stay in the homely Haystack Cottage, dogs enjoyed it too (some nice walks nearby). All very comfortable and cosy!"
United Kingdom
Edward M.
The price is AED 350
AED 429 total
includes taxes & fees
22 Dec - 23 Dec
HAYSTACK COTTAGE SLEEPING 2 NEXT TO FOX COVERT PUB YARM
Exterior
Cosy, 2 Bedroom Cottage in Guisborough Town Centre

Cottage in North Yorkshire

Cosy, 2 Bedroom Cottage in Guisborough Town Centre
10.0 out of 10, Exceptional, (2)
"It’s well situated and a nice place to stay. "
United States
jane
The price is AED 354
AED 432 total
includes taxes & fees
4 Jan - 5 January 2026
Cosy, 2 Bedroom Cottage in Guisborough Town Centre
Exterior
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave

Cottage in High Leven

The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
8.0 out of 10, Very Good, (13)
"Clean, well presented "
United Kingdom
Martin E.
The price is AED 369
AED 447 total
includes taxes & fees
22 Dec - 23 Dec
The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave
Exterior
Luxury couple's country retreat in spectacular location in the North York Moors

Cottage in glaisdale

Luxury couple's country retreat in spectacular location in the North York Moors
10.0 out of 10, Exceptional, (93)
"Property was immaculate. Mark and Moira.where amazing, went way over and above without being asked. We would recommend this wee star of a place to anyone. Views are amazing, and the peace and quiet, just wow. "
United Kingdom
Pau K.
The price is AED 472
AED 1,430 total
includes taxes & fees
5 Jan - 6 January 2026
Luxury couple's country retreat in spectacular location in the North York Moors
Property grounds
Keldholme Cottages 2 - UK11488

Cottage in Keldholme, near Kirkbymoorside

Keldholme Cottages 2 - UK11488
10.0 out of 10, Exceptional, (4)
"We had a lovely 4 night stay.Everything was perfect.Clean, comfortable bed and cosy evenings in front of the fire.Owners were lovely people. We will definitely return."
United States
Jacqueline Allington
The price is AED 998
AED 998 total
includes taxes & fees
2 Jan - 3 January 2026
Keldholme Cottages 2 - UK11488
Exterior
Willow Cottage 4 bedroom Cosy stopover, dogs welcome

Cottage in Thornton-le-Beans

Willow Cottage 4 bedroom Cosy stopover, dogs welcome
10.0 out of 10, Exceptional, (4)
"A most comfortable bungalow in a delightful village. Host kind & welcoming & the bungalow is kept to a good standard. Recommend the Crosby Inn for a meal too. "
United Kingdom
Colin A.
The price is AED 958
AED 1,091 total
includes taxes & fees
23 Dec - 24 Dec
Willow Cottage 4 bedroom Cosy stopover, dogs welcome
Exterior
Chapel Cottage

Cottage in York

Chapel Cottage
2.0 star property
9.4 out of 10, Exceptional, (3)
"The property was beautiful and the owner, David, was very welcoming."
United Kingdom
Geraldine
The price is AED 2,165
AED 2,165 total
includes taxes & fees
5 Jan - 6 January 2026
Chapel Cottage
Property grounds
Keldholme Cottage 1 - UK10992

Cottage in Keldholme, near Kirkbymoorside

Keldholme Cottage 1 - UK10992
9.8 out of 10, Exceptional, (7)
"Excellent for get away from it all beautiful countryside and walks."
United States
John Kelly
The price is AED 1,283
AED 1,283 total
includes taxes & fees
2 Jan - 3 January 2026
Keldholme Cottage 1 - UK10992
Exterior
The Hideaway - Quiet cottage, a short walk from the historic centre of York.

Cottage in Layerthorpe

The Hideaway - Quiet cottage, a short walk from the historic centre of York.
10.0 out of 10, Exceptional, (22)
"Everything was great and we really appreciated the snacks and beverages that were provided. "
United States
John S.
The price is AED 688
AED 899 total
includes taxes & fees
5 Jan - 6 January 2026
The Hideaway - Quiet cottage, a short walk from the historic centre of York.
Exterior
Little Pythorn - UK45253

Cottage in Westerdale, near Castleton

Little Pythorn - UK45253
9.4 out of 10, Exceptional, (3)
"Beautiful cottage, equipped to a high standard, very clean and cosy.Lovely surroundings"
United States
Birgit Lyon
The price is AED 1,170
AED 1,170 total
includes taxes & fees
4 Jan - 5 January 2026
Little Pythorn - UK45253
Exterior
2 bedroom accommodation in Pickering

Cottage in Pickering

2 bedroom accommodation in Pickering
9.0 out of 10, Wonderful, (8)
"Most enjoyable, well appointed cottage comfortable central to the town. Plenty to do and see with the railway nearby. We are looking forward to coming back next year. The Young family. "
United Kingdom
Sonia Y.
The price is AED 1,032
AED 1,032 total
includes taxes & fees
15 Jan - 16 January 2026
2 bedroom accommodation in Pickering
Exterior
The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite

Cottage in High Leven

The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite
8.0 out of 10, Very Good, (6)
"Great place, thanks Angie!"
United Kingdom
Harry C.
The price is AED 862
AED 980 total
includes taxes & fees
22 Dec - 23 Dec
The Byre/Paddock - Sleeping 6 lounge/2 singles /double bed/double bed en suite
Fridge, microwave, oven, dishwasher
Gillygate Boutique Apartment - sleeps 4 guests in 1 bedroom

Cottage in Bootham

Gillygate Boutique Apartment - sleeps 4 guests in 1 bedroom
10.0 out of 10, Exceptional, (32)
"Great location , clean throughout. Easy to find and check in, plenty of parking nearby."
United States
Laura c.
The price is AED 913
AED 913 total
includes taxes & fees
23 Dec - 24 Dec
Gillygate Boutique Apartment - sleeps 4 guests in 1 bedroom
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

Moxy York

Moxy York

10/10 Excellent
"Great staff very friendly and helpful lovely clean warms rooms with tea coffee - excellent breakfast options and variety "
Maureen 2-night trip
Posted 21 hours ago
Moxy York

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