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 favorite

Apartment in Gilling East

4.95 out of 5 average rating, 129 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.

Jun 9 – 16

R2,216 ZAR per night

Guest favorite

Farm stay in Pockley

4.97 out of 5 average rating, 110 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.

Mar 7 – 14

R2,376 ZAR per night

Guest favorite

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!

Jan 8 – 15

R3,585 ZAR per night

Superhost

Train in Helmsley

4.88 out of 5 average rating, 174 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 5 – 12

R3,956 ZAR per night

Guest favorite

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.

Sep 17 – 24

R2,133 ZAR per night

Guest favorite

Guest suite in Rosedale Abbey

4.98 out of 5 average rating, 127 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.

Apr 3 – 10

R2,324 ZAR per night

Guest favorite

Barn in Aislaby, Pickering

4.97 out of 5 average rating, 229 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.

Nov 7 – 14

R4,068 ZAR per night

Guest favorite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Braecote is a peaceful, warm, and welcoming cottage in the picture perfect village of Coxwold. With wide grass verges, honey coloured stone houses and a traditional country pub just up the road, Coxwold is one of the prettiest villages in North Yorkshire. York, Harrogate, Helmsley and Malton are close by, the North York Moors, Yorkshire Dales and east coast all within easy reach. Newburgh Priory is just up the road and Michelin starred Black Swan at Oldstead a short drive away.

Sep 29 – Oct 6

R2,466 ZAR per night

Guest favorite

Tiny home in Newton-on-Rawcliffe

4.99 out of 5 average rating, 190 reviews

The Hide NYM National Park Cosy Cabin with hot tub

Relaxing break for adults on the edge of the North York Moors. A 5 minute drive from Pickering, where you will find shops, bars and restaurants. York/Whitby 45 minute drive. Dalby Forest 30mins, Scarborough 40mins. A tranquil stay in a rural location. Ideal for walkers and cyclists. Includes hot tub. Contact me for discount if you would prefer not to use the hot tub Due to a balcony and limited space, The Hide is not suitable for babies, infants or children. Sorry, no pets.

Oct 15 – 22

R2,548 ZAR per night

Guest favorite

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.

Sep 21 – 28

R2,355 ZAR per night

Guest favorite

Cottage in York

4.99 out of 5 average rating, 346 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.

Mar 20 – 27

R3,637 ZAR per night

Guest favorite

Cottage in Wrelton

4.98 out of 5 average rating, 309 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 16 – 23

R2,490 ZAR 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 favorite

Guest suite in North Yorkshire

4.97 out of 5 average rating, 217 reviews

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

Sep 23 – 30

R2,216 ZAR per night

Guest favorite

Condo in North Yorkshire

4.98 out of 5 average rating, 220 reviews

2 Chiltern Place Malton-Stylish boutique apartment

Mar 21 – 28

R2,438 ZAR per night

Guest favorite

Barn in Kirby Wiske

4.98 out of 5 average rating, 191 reviews

An entire barn conversion in stunning location

Oct 17 – 24

R2,881 ZAR per night

Guest favorite

Home in Kirkbymoorside

4.9 out of 5 average rating, 295 reviews

Oakforge Cottage, a spacious home from home.

Nov 29 – Dec 6

R2,314 ZAR per night

Guest favorite

Guest suite in Sutton-on-the-Forest

5.0 out of 5 average rating, 224 reviews

Countryside location near to York

Feb 24 – Mar 3

R1,986 ZAR per night

Guest favorite

Cottage in Sessay

4.95 out of 5 average rating, 221 reviews

The Cobbler's Cottage

Sep 2 – 9

R2,355 ZAR per night

Guest favorite

Cottage in Helmsley

4.83 out of 5 average rating, 12 reviews

Holiday cottage in lovely Helmsley

Dec 14 – 21

R2,242 ZAR per night

Guest favorite

Tiny home in Wombleton

4.93 out of 5 average rating, 67 reviews

Unique and Cosy Cruck Cottage

Jul 19 – 26

R1,816 ZAR 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
R1,338 ZAR before taxes and fees

Frequently Asked Questions

What are the most popular amenities for House Rentals in Helmsley?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in cottage rentals in Helmsley?
Experience the best of Helmsley with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Helmsley have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Helmsley?
Four-legged friends are welcome in Helmsley. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Helmsley?
Yes! Work meets play with ease at over 30 vacation rentals in Helmsley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Helmsley have free parking?
Absolutely! We offer over 20 cottage rentals with free parking in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Helmsley have wifi?
Absolutely! We offer over 10 house rentals with wifi in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Helmsley?
Helmsley has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Helmsley

Top-rated vacation rentals in Helmsley

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

Guest suite in North Yorkshire

Condo in North Yorkshire

Barn in Kirby Wiske

Home in Kirkbymoorside

Guest suite in Sutton-on-the-Forest

Cottage in Sessay

Cottage in Helmsley

Tiny home in Wombleton

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

Frequently Asked Questions

What are the most popular amenities for House Rentals in Helmsley?

How much does it cost to stay in cottage rentals in Helmsley?

Do house rentals in Helmsley have a kitchen?

Are there pet-friendly vacation rentals in Helmsley?

Are there vacation rentals with a dedicated workspace in Helmsley?

Do cottage rentals in Helmsley have free parking?

Do house rentals in Helmsley have wifi?

Are there family-friendly vacation rentals in Helmsley?

Destinations to explore