Vacation rentals in Helmsley

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Helmsley

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Gilling East

4.95 out of 5 average rating, 128 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.

Aug. 1 – 8

$157 CAD per night

Guest favourite

Farm stay in Pockley

4.97 out of 5 average rating, 109 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.

Nov. 26 – Dec. 3

$168 CAD per night

Guest favourite

Train in Helmsley

4.88 out of 5 average rating, 173 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 !

Oct. 8 – 15

$283 CAD per night

Guest favourite

Cottage in East End

4.99 out of 5 average rating, 240 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!

Aug. 29 – Sep. 5

$261 CAD per night

Guest favourite

Guest suite in Nunnington

4.87 out of 5 average rating, 174 reviews

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

Mar. 6 – 13

$133 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.

Jul. 15 – 22

$157 CAD per night

Guest favourite

Guest suite in Rosedale Abbey

4.98 out of 5 average rating, 126 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.

Mar. 5 – 12

$166 CAD per night

Guest favourite

Barn in Aislaby, Pickering

4.96 out of 5 average rating, 226 reviews

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion designed by architects Bramhall Blenkharn Leonard. It sits on the edge of North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock, woodland & chickens. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom,pizza oven,parking, walkable pub.

Jan. 19 – 26

$288 CAD per night

Guest favourite

Home in Kirkbymoorside

4.9 out of 5 average rating, 295 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.

Oct. 22 – 29

$170 CAD per night

Guest favourite

Home in North Yorkshire

4.89 out of 5 average rating, 176 reviews

Rural homely cottage in North York Moors

Cosy cottage located in the North York Moors National Park with gorgeous big skies! A super base for exploring castles, abbeys, villages and the Heritage coast. Spoilt for choice in eateries from great local pubs to Michelin starred restaurants all with a 10 mile radius. Many guests comment on how peaceful and calm their stay has been. My place is good for couples, solo adventurers, families with children and pets (one, well behaved dog only).

Jan. 25 – Feb. 1

$210 CAD per night

Guest favourite

Apartment in Helmsley

4.98 out of 5 average rating, 147 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.

Jun. 13 – 20

$166 CAD per night

Guest favourite

Cottage in York

4.99 out of 5 average rating, 344 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.

Nov. 4 – 11

$273 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Helmsley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Helmsley's top sights

Helmsley Castle25 locals recommend

National Centre for Birds of Prey14 locals recommend

Helmsley Walled Garden21 locals recommend

Feversham Arms Hotel & Verbena Spa9 locals recommend

The Feathers Hotel8 locals recommend

The Black Swan Hotel6 locals recommend

Other great vacation rentals in Helmsley

Guest favourite

Condo in North Yorkshire

4.98 out of 5 average rating, 218 reviews

2 Chiltern Place Malton-Stylish boutique apartment

Oct. 1 – 8

$177 CAD per night

Guest favourite

Home in Helmsley

4.93 out of 5 average rating, 111 reviews

Holiday at 44 - wonderfully situated for all

Nov. 2 – 9

$386 CAD per night

Guest favourite

Tiny homes in Newton-on-Rawcliffe

4.99 out of 5 average rating, 187 reviews

The Hide NYM National Park Cosy Cabin with hot tub

Jan. 24 – 31

$180 CAD per night

Guest favourite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Nov. 2 – 9

$174 CAD per night

Guest favourite

Cottage in Wrelton

4.98 out of 5 average rating, 309 reviews

Old Forge in Wrelton, North Yorkshire.

Aug. 26 – Sep. 2

$191 CAD per night

Guest favourite

Cottage in Kirkbymoorside

4.87 out of 5 average rating, 329 reviews

Fuchsia Cottage- a cosy getaway

Nov. 3 – 10

$138 CAD per night

Guest favourite

Guest suite in North Yorkshire

4.97 out of 5 average rating, 217 reviews

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

Sep. 1 – 8

$157 CAD per night

Guest favourite

Cottage in Helmsley

4.91 out of 5 average rating, 134 reviews

Cliff Stud Retreat, Helmsley, Frankel Cottage

Oct. 11 – 18

$360 CAD per night

Show all

Quick stats about vacation rentals in Helmsley

Total rentals	50 properties
Rentals with dedicated workspaces	30 properties have a dedicated workspace
Pet-friendly rentals	30 properties allow pets
Family-friendly rentals	30 properties are a good fit for families
Total number of reviews	1.7K reviews
Nightly prices starting at	$97 CAD before taxes and fees

Vacation rentals in Helmsley

Top-rated vacation rentals in Helmsley

Apartment in Gilling East

Farm stay in Pockley

Train in Helmsley

Cottage in East End

Guest suite in Nunnington

Guest suite in Boltby

Guest suite in Rosedale Abbey

Barn in Aislaby, Pickering

Home in Kirkbymoorside

Home in North Yorkshire

Apartment in Helmsley

Cottage in York

Vacation rentals for every style

Cottages

Hotels

Unique stays

Popular amenities for Helmsley vacation rentals

Stay near Helmsley's top sights

Other great vacation rentals in Helmsley

Condo in North Yorkshire

Home in Helmsley

Tiny homes in Newton-on-Rawcliffe

Cottage in Coxwold

Cottage in Wrelton

Cottage in Kirkbymoorside

Guest suite in North Yorkshire

Cottage in Helmsley

Quick stats about vacation rentals in Helmsley

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore