Title: Best Cottages in Helmsley in 2025 | Expedia.co.uk [Helmsley Travel Guide](https://expedia.co.uk/Helmsley.dx4373)[Hotels in Helmsley](https://expedia.co.uk/Helmsley-Hotels.d4373.Travel-Guide-Hotels)[Holiday Rentals in Helmsley](https://expedia.co.uk/Helmsley-Holiday-Rentals.d4373.Travel-Guide-HolidayRentals)[Flights to Helmsley](https://expedia.co.uk/Cheap-Flights-To-Helmsley.d4373.Travel-Guide-Flights)[Helmsley Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Helmsley.d4373.Car-Hire-Guide)[Helmsley Holidays](https://expedia.co.uk/Helmsley.d4373.Holidays-City-Breaks) ![Late afternoon at lovely Helmsley](https://images.trvl-media.com/place/4373/8704ad01-7733-45a2-83a2-610ef1c2c51c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Mark Sage # Search Helmsley Cottages - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=4373&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=4373&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=4373&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [20 Mar - 22 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=4373&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Helmsley Cottages ![Exterior](https://images.trvl-media.com/lodging/77000000/76030000/76026200/76026116/76bb8d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Balcony](https://images.trvl-media.com/lodging/77000000/76030000/76026200/76026116/3e9faea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Private kitchen | Fridge, dishwasher, electric kettle, toaster](https://images.trvl-media.com/lodging/77000000/76030000/76026200/76026116/058ace81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/77000000/76030000/76026200/76026116/3680af94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 29 Bondgate York £483 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/York-Hotels-29-Bondgate.h76026116.Hotel-Information) ![Cottage | Interior](https://images.trvl-media.com/lodging/60000000/59650000/59648000/59647912/87b3a7a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/60000000/59650000/59648000/59647912/95b80546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/60000000/59650000/59648000/59647912/b69bfe0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/60000000/59650000/59648000/59647912/acece1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Cottage York £397 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/York-Hotels-Ivy-Cottage.h59647912.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84010000/84005800/84005725/2112b193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84010000/84005800/84005725/0d15256b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, dishwasher, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/85000000/84010000/84005800/84005725/86468c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/85000000/84010000/84005800/84005725/4ba62cc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cliff House York £491 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/York-Hotels-Cliff-House.h84005725.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99260000/99259000/99258990/3e317dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99260000/99259000/99258990/b87a02c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video game console](https://images.trvl-media.com/lodging/100000000/99260000/99259000/99258990/40d6f974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99260000/99259000/99258990/3e00e47d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stoney Nook Cottage Guisborough 9.2/10 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](https://a.travel-assets.com/egds/marks/flags/ca.svg) Shelley & J. £91 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Guisborough-Hotels-Stoney-Nook-Cottage.h99258990.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95260000/95259200/95259169/e51e0597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/96000000/95260000/95259200/95259169/61b5f78b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95260000/95259200/95259169/cd0556fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, dishwasher, electric kettle, toaster](https://images.trvl-media.com/lodging/96000000/95260000/95259200/95259169/ee1c052f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Dairy Thirsk 10/10 Exceptional (1) "Good experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd £400 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Thirsk-Hotels-The-Old-Dairy.h95259169.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99270000/99261300/99261299/988f8354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99270000/99261300/99261299/3ef76123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99270000/99261300/99261299/921e74f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/100000000/99270000/99261300/99261299/896b1de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy, 2 Bedroom Cottage in Guisborough Town Centre North Yorkshire 10/10 Exceptional (2) "It’s well situated and a nice place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jane £91 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Guisborough-Hotels-Cosy.h99261299.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/14000000/13180000/13172500/13172438/1dd4f775.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Cottage, 2 Bedrooms (Trevena Star) | Private kitchen | Fridge, microwave, oven, electric kettle](https://images.trvl-media.com/lodging/14000000/13180000/13172500/13172438/92eb3fce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Cottage, 2 Bedrooms (Trevena Star) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/14000000/13180000/13172500/13172438/1b30b34e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Cottage, 2 Bedrooms, Ground Floor (Boothferry) | Private kitchen | Fridge, microwave, oven, electric kettle](https://images.trvl-media.com/lodging/14000000/13180000/13172500/13172438/bb865734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Craven Garth Cottages Pickering 9.4/10 Exceptional (46) "Really nice place,friendly landlord and very helpful" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Corin £265 includes taxes & fees 29 Nov - 30 Nov [](https://www.expedia.co.uk/Pickering-Hotels-Craven-Garth-Cottages.h13172438.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33310000/33307600/33307562/52b84ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33310000/33307600/33307562/522992a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33310000/33307600/33307562/270-8b772d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33310000/33307600/33307562/da31b8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glendevon Cottage - Enjoy a short 2-night stay - November availability Staithes 9.6/10 Exceptional (158) "Lovely cottage , clean and fully equipped to meet needs. Lovely, relaxing outdoor seating area . " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Tracey d. £87 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Saltburn-By-The-Sea-Hotels-Glendevon-Cottage-September-Availability-Enjoy-A-Short-2-Night-Stay.h33307562.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18780000/18771300/18771239/90-w2338h1387x0y8-5417784e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18780000/18771300/18771239/0b5d2eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18780000/18771300/18771239/a9cf7d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18780000/18771300/18771239/87737529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury couple's country retreat in spectacular location in the North York Moors glaisdale 10/10 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](https://a.travel-assets.com/egds/marks/flags/uk.svg) Pau K. £310 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Whitby-Hotels-Luxury-Couples-Country-Retreat-In-Spectacular-Location-In-The-North-York-Moors.h18771239.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35700000/35696100/35696025/e4ca18a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35700000/35696100/35696025/28878ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35700000/35696100/35696025/e4dd65e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35700000/35696100/35696025/3b11b6a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Paddock - Sleeping 2 - B & B Yarm double bed en suite /fridge/microwave High Leven 8.0/10 Very good (13) "Clean, well presented " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Martin E. £94 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Yarm-Hotels-The-Paddock-Sleeping-2-B-B-Yarm.h35696025.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103070000/103068200/103068187/3defcbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/104000000/103070000/103068200/103068187/9b792d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103070000/103068200/103068187/6e9622ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103070000/103068200/103068187/df7b51e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willow Cottage 4 bedroom Cosy stopover, dogs welcome Thornton-le-Beans 10/10 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](https://a.travel-assets.com/egds/marks/flags/uk.svg) Colin A. £227 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Northallerton-Hotels-Willow-Cottage-Cosy.h103068187.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/86000000/85540000/85530600/85530502/1ed42e62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dishwasher, high chair](https://images.trvl-media.com/lodging/86000000/85540000/85530600/85530502/444b7c3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85530600/85530502/54da59e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/86000000/85540000/85530600/85530502/07f4513b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keldholme Cottages 2 - UK11488 Keldholme, near Kirkbymoorside 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline Allington £251 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/York-Hotels-2-Bedroom-Accommodation-In-Keldholme.h85530502.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99120000/99114500/99114436/2e15c60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99120000/99114500/99114436/811f0e92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99120000/99114500/99114436/af5ec5ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99120000/99114500/99114436/3650bdd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Pythorn - UK45253 Westerdale, near Castleton 9.4/10 Exceptional (3) "Beautiful cottage, equipped to a high standard, very clean and cosy.Lovely surroundings" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Birgit Lyon £238 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Whitby-Hotels-1-Bedroom-Accommodation-In-Westerdale.h99114436.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90310000/90302100/90302087/30f83822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90310000/90302100/90302087/5796b799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/91000000/90310000/90302100/90302087/634461cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/91000000/90310000/90302100/90302087/9c876f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hideaway - Quiet cottage, a short walk from the historic centre of York. Layerthorpe 10/10 Exceptional (22) "Everything was great and we really appreciated the snacks and beverages that were provided. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John S. £198 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/York-Hotels-Quiet-Cottage.h90302087.Hotel-Information) ![Cottage | Exterior](https://images.trvl-media.com/lodging/31000000/31000000/30995900/30995884/718017fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Outdoor dining](https://images.trvl-media.com/lodging/31000000/31000000/30995900/30995884/1a5fea78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Private kitchen | Fridge, stovetop, high chair, cookware/dishes/utensils](https://images.trvl-media.com/lodging/31000000/31000000/30995900/30995884/2245de80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | 2 bedrooms, individually decorated, individually furnished, bed sheets](https://images.trvl-media.com/lodging/31000000/31000000/30995900/30995884/bf96cb62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Croft Granary York 10/10 Exceptional (5) "We had a really good stay. The cottage is beautiful and equipped with absolutely everything you could ever need. Our son really enjoyed the garden, in particular the Wendy House which was also kitted out with toys, which was a lovely bonus. The village is peaceful but perfect for a nice walk. We would thoroughly recommend the property and would stay again. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Leslie £307 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/York-Hotels-Croft-Granary.h30995884.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/86000000/85540000/85536500/85536493/3682abdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/86000000/85540000/85536500/85536493/db6f60b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dishwasher](https://images.trvl-media.com/lodging/86000000/85540000/85536500/85536493/e38c3eae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/86000000/85540000/85536500/85536493/45069021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keldholme Cottage 1 - UK10992 Keldholme, near Kirkbymoorside 10/10 Exceptional (5) "Excellent for get away from it all beautiful countryside and walks." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John Kelly £241 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/York-Hotels-2-Bedroom-Accommodation-In-Keldholme.h85536493.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/53000000/52110000/52106200/52106136/dcc356a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/53000000/52110000/52106200/52106136/aa46d0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/53000000/52110000/52106200/52106136/54beb91b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/53000000/52110000/52106200/52106136/9eddab7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4 bedroom accommodation in Goathland Goathland 8.0/10 Very good (1) "Will definitely go back again my family loved it had a power cut made it more adventurous loved every minute off it neighbours across the way gave us some candles next day didn't use them but people made you welcome" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fredrick Dobbs £502 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Whitby-Hotels-4-Bedroom-Accommodation-In-Goathland.h52106136.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/66000000/65710000/65708800/65708712/e4277a83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dishwasher, high chair](https://images.trvl-media.com/lodging/66000000/65710000/65708800/65708712/bfb29d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/66000000/65710000/65708800/65708712/f5039035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/66000000/65710000/65708800/65708712/2f939a8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 bedroom accommodation in Pickering Pickering 9.0/10 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](https://a.travel-assets.com/egds/marks/flags/uk.svg) Sonia Y. £210 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Pickering-Hotels-2-Bedroom-Accommodation-In-Pickering.h65708712.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/77000000/76030000/76026600/76026553/a690bee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76030000/76026600/76026553/63eba5d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76030000/76026600/76026553/ab35804c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/77000000/76030000/76026600/76026553/c8c70c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Winds Cottage Guisborough 10/10 Exceptional (1) "A great little place to chill out. Location brilliant for accessing beaches/ harbours and forest walks. Good selection of pubs / takeaways and little cafés. Hot tub a real bonus ! Beds very comfy ....perfect !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma £457 includes taxes & fees 4 Dec - 5 Dec [](https://www.expedia.co.uk/Guisborough-Hotels-2-Bedroom-Accommodation-In-Guisborough.h76026553.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/40000000/39540000/39535900/39535849/e343731f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/40000000/39540000/39535900/39535849/8fa21fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/40000000/39540000/39535900/39535849/292456e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/40000000/39540000/39535900/39535849/ec90eb88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillygate Boutique Apartment - sleeps 4 guests in 1 bedroom Bootham 10/10 Exceptional (32) "Great location , clean throughout. Easy to find and check in, plenty of parking nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura c. £239 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/York-Hotels-Gillygate-Boutique-Apartment-Sleeps-4-Guests-In-1-Bedroom.h39535849.Hotel-Information) 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](https://expedia.co.uk/Hotel-Search?startDate=2025-12-10&endDate=2025-12-11®ionId=4373&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_BF_PROMO_4373) ## Find holiday rentals that suit your style Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=COTTAGE) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=APARTMENT) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=CABIN) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=APART_HOTEL) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=CHALET) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=CONDO) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Helmsley%2C+York%2C+England%2C+United+Kingdom®ionId=4373&latLong=54.246498%2C-1.056262&adults=2&startDate=2026-02-24&d1=2026-02-24&endDate=2026-02-27&d2=2026-02-27&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHelmsley-Cottages.d4373-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHelmsley-Cottages.d4373-aaCottages.Travel-Guide-Accommodation) ## Top Helmsley Hotel Reviews ![Moxy York](https://images.trvl-media.com/lodging/37000000/36770000/36762100/36762017/da3c8297_y.jpg) ### Moxy York 10/10 Excellent "Lovely hotel close to centre, great staff!" [](https://expedia.co.uk/York-Hotels-Moxy-York.h36762017.Hotel-Information) ![The Feathers Hotel, Helmsley, North Yorkshire](https://images.trvl-media.com/lodging/15000000/14890000/14889400/14889397/10ef573e_y.jpg) ### The Feathers Hotel, Helmsley, North Yorkshire 10/10 Excellent "Wonderful accommodation and food, with excellent, friendly service! " [](https://expedia.co.uk/York-Hotels-The-Feathers-Hotel.h14889397.Hotel-Information) ![Leonardo Hotel Middlesbrough](https://images.trvl-media.com/lodging/1000000/550000/544600/544541/745f04cf_y.jpg) ### Leonardo Hotel Middlesbrough 10/10 Excellent "excellent apart having to leave before my stay had ended " [](https://expedia.co.uk/Middlesbrough-Hotels-Jurys-Inn-Middlesbrough.h544541.Hotel-Information) ![Dean Court Hotel](https://images.trvl-media.com/lodging/1000000/10000/7500/7413/3ef64605_y.jpg) ### Dean Court Hotel 10/10 Excellent "Fab room Very clean Fantastic view of The Minster Brilliant staff Really helpful Very friendly " [](https://expedia.co.uk/York-Hotels-Dean-Court-Hotel.h7413.Hotel-Information) ![No.1 by GuestHouse, York](https://images.trvl-media.com/lodging/1000000/20000/11800/11750/a82be83d_y.jpg) ### No.1 by GuestHouse, York 10/10 Excellent "Cannot criticise anything during our short break. It was excellent from start to finish. All of the staff were perfect and the hotel was a pleasure to stay at." [](https://expedia.co.uk/York-Hotels-The-Grange-Hotel.h11750.Hotel-Information) ![The Golden Fleece Hotel, Thirsk, North Yorkshire](https://images.trvl-media.com/lodging/1000000/40000/34200/34191/704fdfdf_y.jpg) ### The Golden Fleece Hotel, Thirsk, North Yorkshire 10/10 Excellent "The staff were exceptional as we had gone to visit a very poorly friend. Our plans changed yesterday and today hourly and we were allowed to stay in their carpark until we left just after 2 pm. Our friend is home from hospital but have not had chance to catch up but we enjoyed our time in Thirsk a beautiful place great for shopping " [](https://expedia.co.uk/Thirsk-Hotels-The-Golden-Fleece-Hotel.h34191.Hotel-Information) ![The Black Swan - The Inn Collection Group](https://images.trvl-media.com/lodging/1000000/30000/22500/22461/ffc1e9c7_y.jpg) ### The Black Swan - The Inn Collection Group 10/10 Excellent "Berg good hotel, great service breakfast was excellent " [](https://expedia.co.uk/York-Hotels-The-Black-Swan-At-Helmsley.h22461.Hotel-Information) ![The Churchill Hotel](https://images.trvl-media.com/lodging/2000000/1780000/1779800/1779789/86f49598_y.jpg) ### The Churchill Hotel 10/10 Excellent "Rooms were spotless , staff very friendly & helpful, location was a 5 min walk into town with the Minster on your door step ,will definitely stay here again on my next visit ." [](https://expedia.co.uk/York-Hotels-The-Churchill-Hotel.h1779789.Hotel-Information) ![Burn Hall Hotel](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753368/8728b720_y.jpg) ### Burn Hall Hotel 10/10 Excellent " On arrival the staff was very polite and welcoming. The room was very clean, spacious, comfy bed and a great size bathroom too. The views were amazing. Gorgeous breakfast. Could not fault it " [](https://expedia.co.uk/York-Hotels-Burn-Hall-Hotel.h1753368.Hotel-Information) ## Find out more about Helmsley ## Helmsley Cottages information | Number of reviews | 245 | | --- | --- | | Accommodation | 906 Cottages | | Lowest Price | £87 | | Highest Price | £502 | ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [3 Star Hotels in Harome](https://www.expedia.co.uk/3Star-Harome-Hotels.s30-0-d3000452777.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Ampleforth](https://www.expedia.co.uk/4Star-Ampleforth-Hotels.s40-0-d3000388919.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Harome](https://www.expedia.co.uk/4Star-Harome-Hotels.s40-0-d3000452777.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Nawton](https://www.expedia.co.uk/5Star-Nawton-Hotels.s50-0-d6337620.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Old Byland](https://www.expedia.co.uk/5Star-Old-Byland-Hotels.s50-0-d3000010305.Travel-Guide-Filter-Hotels) - 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