Vacation rentals in Helmsley

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Top-rated vacation rentals in Helmsley

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Guest favourite

Apartment in Gilling East

4.95 out of 5 average rating, 130 reviews

Fairfax View - delightful annexe cottage, Gilling

Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

Jan. 12 – 19

$158 CAD per night

Guest favourite

Farm stay in Pockley

4.97 out of 5 average rating, 113 reviews

Couple's Bothy near Helmsley in the National Park

Take it easy at this unique and tranquil getaway. Our converted barn offers a cosy, self-catering retreat for two on our remote, but accessible farm in the North York Moors National Park. The Bothy is a self-contained, open space providing king sized bed, ensuite, kitchen, sitting area, outside terrace sun trap & free WiFi. The Bothy has been completed to an exceptionally high standard combining beautiful detailing and practicality. We are blessed with a wonderful location for walking & cycling.

Jan. 20 – 27

$170 CAD per night

Guest favourite

Condo in North Yorkshire

4.98 out of 5 average rating, 222 reviews

2 Chiltern Place Malton-Stylish boutique apartment

Relax in this luxury boutique apartment located within a stylish, distinctive merchants building in the heart of Malton. The accommodation comprises of: entrance hall with guest cloakroom, utility room, open plan living area with contemporary feature inset fire, high specification kitchen and dining area. Master bedroom suite, king bed, luxury en-suite & private terrace. There is WiFi and underfloor heating. Free private parking on the property and space for 2 bikes within the storage areas.

Jan. 27 – Feb. 3

$182 CAD per night

Guest favourite

Cottage in East End

4.99 out of 5 average rating, 241 reviews

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

Feb. 17 – 24

$263 CAD per night

Superhost

Train in Helmsley

4.88 out of 5 average rating, 175 reviews

Unique Railway Carriage - In the Heart of Helmsley

Helmsley Railway Carriage…..A Special Experience ! Our 1887, 3rd Class Victorian Railway Carriage converted to 5* standards. With all the facilities of a self-catering property including a full kitchen and lounge/dining area including a welcome pack of essentials included in your rate. In service to 1905, running between York & Scarborough, the Carriage ended up at Helmsley Railway Station, then brought to our property in that year ! The UK's oldest & unusual Train Carriage accommodation !

Mar. 6 – 13

$286 CAD per night

Guest favourite

Guest suite in Boltby

4.98 out of 5 average rating, 108 reviews

Boltby, Cosy North York Moors Snug with Log Burner

Barn Owl Snug is tucked away in the pretty village of Boltby in the North York Moors National Park. The perfect space to recharge and have a relaxing break. The snug is self-contained. Downstairs is the living, dining and full kitchen area with a log burner for those cosy evenings. Up a spiral staircase is a large, bright bedroom with king size bed and separate full family bathroom. Double doors open onto a private decked area. Washing machine / freezer / bike storage. Wi-Fi and parking.

Mar. 7 – 14

$158 CAD per night

Guest favourite

Guest suite in North Yorkshire

4.97 out of 5 average rating, 219 reviews

*The Vicarage Annexe, Carlton, North Yorks 1BR S/C

The Vicarage Annexe is a beautiful, one double-bedroom facility situated at the foot of the Cleveland Hills. The building was originally built as a prayer and study room for the Vicarage. This is now a self-contained living area with en-suite facilities. The Annexe is located in the picturesque village of Carlton-in-Cleveland, which is in the North Yorkshire Moors National Park and this is an ideal location for a couple who enjoy the countryside for relaxing, sightseeing, walking or cycling.

Sep. 26 – Oct. 3

$158 CAD per night

Guest favourite

Guest suite in Rosedale Abbey

4.98 out of 5 average rating, 131 reviews

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Feb. 25 – Mar. 4

$164 CAD per night

Guest favourite

Home in Kirkbymoorside

4.9 out of 5 average rating, 298 reviews

Oakforge Cottage, a spacious home from home.

Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.

Jan. 25 – Feb. 1

$169 CAD per night

Guest favourite

Apartment in Helmsley

4.98 out of 5 average rating, 148 reviews

The Flat @ 2 Castlegate

Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

Oct. 22 – 29

$168 CAD per night

Guest favourite

Cottage in York

4.99 out of 5 average rating, 348 reviews

Whootin Owl Barn

Whootin Owl Barn is a smart luxury detached barn with private screened hot tub overlooking private woodland on a tranquil country lane in the heart of North Yorkshire only 9 miles from Castle Howard and 25 mins from York. If you are looking for a romantic modern and ultra clean property in a beautiful private location for a short break or Holiday getaway or looking for a base to explore North Yorkshire, look no further.

Feb. 5 – 12

$269 CAD per night

Guest favourite

Cottage in Wrelton

4.98 out of 5 average rating, 311 reviews

Old Forge in Wrelton, North Yorkshire.

This cottage, in the village of Wrelton near Pickering, was a 19th century blacksmith's forge and has now been renovated into a delightful living space complete with fully-equipped kitchen, large living room area, bathroom with walk-in shower and a cosy bedroom located on a mezzanine floor which is reached via a spiral staircase. The Old Forge offers a great location for a relaxing stay in beautiful North Yorkshire.

Aug. 13 – 20

$179 CAD per night