Holiday rentals in Helmsley

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Top-rated holiday rentals in Helmsley

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

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Top guest favourite
The open-plan space features a spacious bed with plush bedding and two leather armchairs positioned beside a wooden dining table. Natural light enters through a window with checked curtains, creating a cozy ambiance. A flat-screen TV is mounted on the wall nearby.
Guest house
4.99 out of 5 average rating, 171 reviews

The Little House Peaceful & self-contained

Located in the centre of the lovely village of Kilburn on the edge of the North Yorkshire Moors National Park, the Little House is peaceful, cosy and self-contained, tucked away from the general hustle and bustle of the village with a safe garden for dogs and children. The Forresters Arms, serving local ales and meals, is a mere 20m across the square, it is best to reserve a table. The Mouseman Furniture Centre is just around the corner and the White Horse of Kilburn is a good walk up the hill.

Top guest favourite
A living area is depicted featuring a plush red sofa adorned with floral cushions. A rustic wooden coffee table centers the room, while a potted plant adds a touch of greenery. Light streams in through a large window, with a staircase visible in the background.
Home
4.98 out of 5 average rating, 107 reviews

Central Fully Ensuite house sleeps 6 dog friendly

The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.

Top guest favourite
A cozy suite is featured, with a spacious bed neatly made. A comfortable seating area contains a gray sofa with decorative pillows, a vintage trunk, and a piano. Natural light pours through two windows, illuminating the wooden floor and soft wall colors.
Guest suite
4.87 out of 5 average rating, 207 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.

Guest favourite
The exterior of the cottage showcases a charming stone facade with a red-tiled roof. A staircase leads to the entrance, and a large parasol shades a wooden table and chairs on a gravel patio. Lush greenery and trees surround the property.
Cottage
4.98 out of 5 average rating, 324 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!

Top guest favourite
A cozy snug room is presented with a blue sofa featuring decorative cushions, accompanied by a striped armchair with an orange accent pillow. Two lamps provide soft lighting, and a round mirror is mounted on a green accent wall, enhancing the inviting ambiance.
Home
4.98 out of 5 average rating, 199 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.

Top guest favourite
A woodfired hot tub is set in a private outdoor area, surrounded by warm lighting and a rustic wooden structure. The evening sky deepens to twilight, enhancing the tranquil ambiance. Logs are neatly arranged nearby, providing easy access for fueling the hot tub.
Farm stay
4.98 out of 5 average rating, 196 reviews

Couple's Bothy near Helmsley in the National Park

Unwind at this unique and tranquil getaway. Our converted barn offers a cosy, self-catering retreat for two with a woodfired hot tub, 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. A great location for walking & cycling.

Top guest favourite
The living kitchen area features exposed beams and floral wallpaper. A cozy seating arrangement is complemented by a plush rug and a vintage cast iron stove. Kitchen amenities are visible, including a stove, oven, and storage. Warm light fixtures illuminate the space.
Guest suite
4.99 out of 5 average rating, 252 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.

Top guest favourite
The exterior of a quaint stone cottage is presented, featuring a bright yellow front door. Two small windows are framed on either side, with planters containing vibrant flowers positioned on either side of the entrance. A clear blue sky is visible overhead.
Tiny home
4.95 out of 5 average rating, 102 reviews

Unique and Cosy Cruck Cottage

Cruck Cottage is in the pretty village of Wombleton, close to the market towns of Helmsley and Kirkbymoorside, on the edge of the North Yorkshire Moors National Park. You will have off street parking and a private patio with seating area and BBQ. The 15C Plough pub (Good Food Guide listed) is just a short walk away. We are ideally located with easy access to the beautiful North York Moors National Park, James Herriot Country, Whitby and the spectacular North Yorkshire coastline.

Top guest favourite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny home
4.98 out of 5 average rating, 177 reviews

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annex is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Top guest favourite
A charming stone cottage is nestled among lush greenery, surrounded by tall trees. Two white chairs are positioned outside the entrance, inviting relaxation. The traditional roof features rustic tiles, and a flowering shrub adds a touch of nature to the setting.
Guest house
5 out of 5 average rating, 103 reviews

Mill House Annex, Oldstead

This bolthole has been lovingly refurbished to a high standard throughout, providing guests with a comfortable and cosy home-from-home. There is a spacious bedroom with a king-size bed, a modern bathroom fitted with underfloor heating and a sperate bath and shower. The living room has a cosy log fire and large dining table. The kitchen is well appointed and kitted out to meet all your culinary needs. Take it easy at this unique and tranquil getaway.

Top guest favourite
Multiple paned windows frame a pleasant view of greenery and colorful trees outside. A decorative bowl and two ceramic jugs rest on the windowsill, allowing natural light to fill the space.
Flat
4.98 out of 5 average rating, 206 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.

Superhost
Holiday home
4.8 out of 5 average rating, 101 reviews

Garden Cottage - Peaceful in the Heart of Helmsley

A Unique Self-Catering Experience ! Stay in your own private luxury Home-from-Home private cottage, attached to our 1560-Built property opposite the Market square. Your own private entrance leads into your own Dining Room and Kitchenette area which leads into your own large separate Lounge. A well-appointed Shower Room is situated on the ground floor. Upstairs is a large Bedroom with fitted wardrobes and TV.

Popular amenities for Helmsley holiday rentals

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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 30 homes with a kitchen, over 30 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 30 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 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 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 30 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 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

All about Helmsley

Nestled amid the 554 square miles of the North York Moors National Park, Helmsley — located on the banks of the River Rye — is the quintessential English market town, boasting cobbled market squares, honeyed-stone cottages, historic inns, and 51 listed buildings, all looked over by the ancient ruins of the 12th-century Helmsley Castle. Circled by the most wondrous countryside, Helmsley really is the perfect place to base yourself as you explore the glories of the surrounding landscape: Two of the finest trails in the United Kingdom, The Cleveland Way and the Ebor Way, both start in the town. The town comes to life on market day (Friday), when hundreds of independent traders descend to peddle their wares. But if the hustle and bustle gets to be too much, there’s also a heated outdoor community pool to enjoy in the summer months.

What are the top things to do in Helmsley?

Helmsley Castle

First built around 1120, this castle has lived many lives. Initially designed as a defensive fortress, it became an elaborate Tudor mansion, then a Civil War stronghold, and later a romantic Victorian ruin. Now you can enjoy a hands-on exhibition illustrating its many guises and an audio tour of the site. Beside the castle is Helmsley Walled Garden, a beautifully restored 18th-century garden that is an oasis of tranquility.

Rievaulx Abbey

Just a couple of miles from Helmsley Castle (there’s a trail taking you on a scenic route from one site to the other) are more impressive ruins, though of a more ecclesiastical nature. Rievaulx Abbey was once one of England’s most powerful Cistercian monasteries before being dissolved by Henry VIII in 1538. A detailed audio tour highlights the fascinating history of this very special place.

Nunnington Hall

One of the finest manor houses in the United Kingdom is only 6 miles southeast of Helmsley. Erected in the 17th century and now maintained by the National Trust, Nunnington Hall features a delightful walled garden where peacocks stroll. As well as the wonderful period rooms and an astonishing collection of miniature rooms, the Hall also stages contemporary art and photography exhibitions.

Quick stats about holiday rentals in Helmsley

  • Total holiday rentals

    Explore 50 holiday rentals in Helmsley

  • Nightly prices starting at

    Helmsley holiday rentals start at £82 per night before taxes and fees

  • Verified guest reviews

    Over 1,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Helmsley holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Helmsley rentals

  • 4.8 Average rating

    Helmsley stays are highly rated by guests – averaging 4.8 out of 5!

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Helmsley