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Vacation rentals in Helmsley

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Top-rated vacation rentals in Helmsley

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

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Cottage in North Yorkshire

4.84 out of 5 average rating, 108 reviews

Luxury Old Stone Cottage, Beautifully Presented

We do not accept children or pets. The Old Chauffeurs Cottage, beautiful, luxurious, warm and cosy. Two bedrooms with comfortable King size beds and a great lounge and kitchen. A downstairs toilet & full bathroom upstairs. It provides a good base for walkers & sightseers as we are close to the North York Moors, the steam railway at Pickering, Castle Howard & York. There is free WiFi & parking plus secure storage for cycles. We have a short video Youtube@tara101 playlist The Chauffeurs Cottage

Rental unit in Gilling East

4.96 out of 5 average rating, 156 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.

Farm stay in Pockley

4.98 out of 5 average rating, 131 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.

Train in Helmsley

4.87 out of 5 average rating, 193 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 !

Cottage in East End

4.99 out of 5 average rating, 269 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!

Home in North Yorkshire

4.98 out of 5 average rating, 130 reviews

Gorgeous country cottage in a stunning location

A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

Guest suite in North Yorkshire

4.97 out of 5 average rating, 266 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.

Guest suite in Rosedale Abbey

4.99 out of 5 average rating, 169 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.

Cottage in Coxwold

4.99 out of 5 average rating, 173 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.

Home in Kirkbymoorside

4.9 out of 5 average rating, 354 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.

Home in Hovingham

4.89 out of 5 average rating, 133 reviews

The Shed, Hovingham, York

An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.

Rental unit in Helmsley

4.98 out of 5 average rating, 169 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Helmsley vacation rentals

Free parking on premises

Air conditioning

Stay near Helmsley's top sights

Helmsley Castle25 locals recommend

Helmsley Walled Garden21 locals recommend

National Centre for Birds of Prey14 locals recommend

Duncombe Park14 locals recommend

Feversham Arms Hotel & Verbena Spa9 locals recommend

The Helmsley Arts Centre8 locals recommend

Other great vacation rentals in Helmsley

Vacation home in Helmsley

4.82 out of 5 average rating, 45 reviews

Honeysuckle Cottage

Home in Helmsley

5 out of 5 average rating, 70 reviews

Modern spacious fully ensuite house, dog friendly

Home in Helmsley

4.93 out of 5 average rating, 15 reviews

Forge Cottage, Helmsley

Barn in Yearsley

4.99 out of 5 average rating, 70 reviews

Herriot Country peaceful retreat

Cottage in Helmsley

4.81 out of 5 average rating, 16 reviews

Holiday cottage in lovely Helmsley

Cottage in Wrelton

4.98 out of 5 average rating, 352 reviews

Old Forge in Wrelton, North Yorkshire.

Cottage in Lockton

4.98 out of 5 average rating, 65 reviews

Rowans Cottage - distinctive 1 bed restoration

Train in Nawton

4.89 out of 5 average rating, 103 reviews

Station Cottage Carriage

Quick stats about vacation rentals in Helmsley

Total rentals
40 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

What are the most popular amenities for Cottage Rentals in Helmsley?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 20 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 $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Helmsley have a kitchen?
Absolutely! We offer over 20 cottage 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 20 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 20 vacation rentals in Helmsley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Helmsley have free parking?
Absolutely! We offer over 10 house rentals with free parking in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Helmsley have wifi?
Absolutely! We offer over 20 cottage 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.

Destinations to explore