Vacation rentals in Helmsley

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Top-rated vacation rentals in Helmsley

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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.

Nov 3 – 10

G$23,596 GYD per night

Guest favorite

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 30 – Dec 7

G$25,294 GYD per night

Guest favorite

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 !

Feb 22 – Mar 1

G$42,109 GYD per night

Guest favorite

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!

Mar 18 – 25

G$38,146 GYD per night

Guest favorite

Guest suite in Nunnington

4.86 out of 5 average rating, 175 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 21 – 28

G$19,385 GYD per night

Guest favorite

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.

Oct 5 – 12

G$24,641 GYD per night

Guest favorite

Barn in Aislaby, Pickering

4.96 out of 5 average rating, 228 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 21 – 28

G$43,314 GYD per night

Guest favorite

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.

Feb 4 – 11

G$23,996 GYD per night

Guest favorite

Home in North Yorkshire

4.89 out of 5 average rating, 177 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).

Jul 3 – 10

G$30,157 GYD per night

Guest favorite

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.

Sep 5 – 12

G$25,071 GYD per night

Guest favorite

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.

Feb 2 – 9

G$38,700 GYD 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.

Sep 27 – Oct 4

G$27,608 GYD 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 17 – 24

G$23,596 GYD 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

Aug 17 – 24

G$22,694 GYD per night

Guest favorite

Tiny home in Newton-on-Rawcliffe

4.99 out of 5 average rating, 188 reviews

The Hide NYM National Park Cosy Cabin with hot tub

Feb 16 – 23

G$27,130 GYD per night

Guest favorite

Cottage in Kirkbymoorside

4.87 out of 5 average rating, 329 reviews

Fuchsia Cottage- a cosy getaway

Oct 25 – Nov 1

G$20,933 GYD per night

Guest favorite

Home in Helmsley

4.93 out of 5 average rating, 111 reviews

Holiday at 44 - wonderfully situated for all

Oct 11 – 18

G$59,964 GYD per night

Guest favorite

Cottage in Coxwold

4.99 out of 5 average rating, 162 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Dec 7 – 14

G$26,251 GYD per night

Guest favorite

Condo in North Yorkshire

4.98 out of 5 average rating, 219 reviews

2 Chiltern Place Malton-Stylish boutique apartment

Mar 21 – 28

G$26,089 GYD per night

Guest favorite

Barn in Kirby Wiske

4.98 out of 5 average rating, 191 reviews

An entire barn conversion in stunning location

Sep 16 – 23

G$30,127 GYD 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
G$14,627 GYD 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 free parking, over 10 homes with a kitchen, 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

Guest suite in Boltby

Tiny home in Newton-on-Rawcliffe

Cottage in Kirkbymoorside

Home in Helmsley

Cottage in Coxwold

Condo in North Yorkshire

Barn in Kirby Wiske

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