House holiday rentals in Helmsley

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Quick stats about house rentals in Helmsley

Total holiday rentals
Explore 10 holiday rentals in Helmsley
Nightly prices starting at
Helmsley holiday rentals start at $308 AUD per night before taxes and fees
Verified guest reviews
Over 530 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities
Wi-Fi availability
10 of Helmsley holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Helmsley rentals
4.9 Average rating
Helmsley stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Helmsley

Guests agree: These houses are highly rated for location, cleanliness and more.

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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 in Helmsley

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.

LocationFamilyIndoor spaces

4.98 out of 5 average rating, 118 reviews

Top Guest favourite

The cottage exterior features natural stone walls with a rustic charm. A red-tiled roof complements the warm tones of the facade. A spacious patio area includes wicker seating and a small table, ideal for outdoor relaxation. Nearby, greenery and trees provide a peaceful setting.

Home in Keldholme

Highfield Annex with off St Parking in Keldholme

Enjoy a tranquil getaway at Heather Annex! Explore the North York Moors by foot; cycle Dalby Forest’s trails or ride the iconic Pickering steam train to Whitby. Visit charming market towns like Helmsley and Kirkbymoorside. Nearby, discover TV's 'Bangers & Cash' or York. Coastal towns, Whitby & Scarborough are less than an hour away. Walk to local pubs and cafes. Return to 1/2 an acre of grounds featuring American Miniature Horses & hens. Or simply unwind on the Patio & have a peaceful stay!

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 117 reviews

Top Guest favourite

Home in Welburn

Luxury Country Cottage Hot Tub Spa Retreat | York

Snowdrop Cottage is a luxurious 5★ retreat nestled in the picturesque village of Welburn, surrounded by the breathtaking Howardian Hills, just minutes from the iconic Castle Howard, the city of York and the Yorkshire coastline. An idyllic escape, this beautifully styled boutique cottage features a private garden spa & hot tub, cosy log burner & romantic four-poster king-size bed - the perfect setting for couples, families and dog walkers to relax, reconnect and explore the Yorkshire countryside.

LocationFamilyCleanliness

4.98 out of 5 average rating, 127 reviews

Top Guest favourite

Home in West Layton

Country Manor House - Nr Richmond North Yorkshire

No.2 West Layton Manor is part of an Historic Victorian Manor House built in 1872. The property provides the perfect setting for families and friends gathering for special occasions or holidays in beautiful North Yorkshire. The property boasts 6 kingsize bedrooms equipped with 6 full ensuite bathrooms. A further 7th bathroom is located on the ground floor. There are 3 large reception rooms, 2 open log fires, and approximately 1/2 an acre of gardens. There is private parking for 8 vehicles.

FamilyLocationHospitality

4.99 out of 5 average rating, 116 reviews

Top Guest favourite

Home in North Yorkshire

Gorgeous country cottage, Nawton near Helmsley

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.

FamilyValueCheck-in

4.98 out of 5 average rating, 232 reviews

Top Guest favourite

The three-storey town house features a classic stone facade with large windows that allow natural light to fill the interior. The entrance includes two white doors, each framed by decorative columns, with a small set of steps leading up to them.

Home in Kirkbymoorside

The Town House

This family and dog friendly three storey town house in the centre of Kirkbymoorside gives easy access to shops, pubs, the local market and childrens play area, and a 1 minute walk finds you in open fields with public footpaths. Stroll around the outskirts of town or head off on foot to explore the moors, woodlands and villages. The coast, Dalby and Cropton forest, North York Moors National Park, Pickering steam railway, Flamingoland, Malton and the city of York are in easy driving distance.

ValueFamilyCleanliness

4.93 out of 5 average rating, 101 reviews

Top Guest favourite

The exterior of a charming stone cottage is displayed, featuring a distinctive red pitched roof. Flower pots with blooming plants adorn the entrance. A well-maintained gravel pathway leads to the door, surrounded by lush greenery and shrubbery.

Home in Ampleforth

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to relax, listen to the wildlife and enjoy the beautiful countryside. The pretty market town Helmsley is less than 10 minutes drive, with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants. York is 45 mins drive and an hour to the coast for beach walks.

ValueLocationBathroom

4.97 out of 5 average rating, 145 reviews

Guest favourite

A bright bedroom features a spacious bed with soft bedding, complemented by a decorative chest of drawers. Natural light floods the room, highlighting the neutral decor. A doorway leads to an en-suite bathroom, and a comfortable seating area is visible in the background.

Home in Kirkbymoorside

Oakforge Cottage, a spacious home from home.w

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.

LocationFamilyParking

4.9 out of 5 average rating, 476 reviews

Guest favourite

The exterior of a charming stone cottage is depicted, featuring a blue front door with a silver door knocker. Lush greenery lines the walkway, and flower boxes adorn the nearby windows. The peaceful street is visible, with additional cottages and trees in the distance.

Home in Hovingham

Home Cottage -North Yorkshire - Dog Friendly

Picture perfect Stone cottage located in the heart of the pretty village of Hovingham, on the edge of the Howardian Hills, an area of outstanding natural beauty. 2 bedrooms and 2 bathrooms. Cosy lounge with log burner and smart tv and of course wifi. A fully equipped Country style kitchen, with dining area and a Utility Room = the perfect dog bedroom!! Enclosed Courtyard garden. Perfect holiday retreat

LocationFamilyGetting around

4.84 out of 5 average rating, 311 reviews

Top Guest favourite

A charming garden area features a white outdoor table and chairs set upon a lush green lawn. The historic stone structure of Westerdale Hall is visible in the background, framed by mature trees and hedging, providing a serene and inviting outdoor space.

Home in Westerdale

Beautiful, quiet and private historic Coach House

My place is in the heart of the North York Moors and close to the Yorkshire Heritage Coast. surrounded by stunning views, open countryside and within easy reach of all the attractions of the Yorkshire moors. The property is in an unspoilt, peaceful and idilic location. with private courtyard parking and established gardens

LocationFamilyBackyard

4.95 out of 5 average rating, 180 reviews

Top Guest favourite

A historic building is set against a backdrop of blue sky, with seasonal flowers blooming in the foreground. Crocuses and small yellow flowers create a vibrant carpet of color across the lush, green lawn, inviting relaxation and appreciation of the natural surroundings.

Home in Langton

North Wing of Langton Hall - Grade 2 listed

The Grade 2 listed North Wing of Langton Hall is the oldest part of the Estate. The property sleeps 13 comfortably with ample space for relaxing. The property comprises of a large family kitchen with a table dating back to the early 1800's Please note this property is located on a NO SMOKING premises

FamilyValueView

4.94 out of 5 average rating, 197 reviews

Top Guest favourite

A inviting sitting room features a comfortable green sofa adorned with decorative cushions. A wooden coffee table sits on a textured rug, and a log burner is positioned beneath a large mirror. A flat-screen TV is mounted on the wall opposite a window, allowing natural light to fill the space.

Home in Helmsley

31 Bridge Street

This beautiful 18th century cottage sits in the heart of the lovely North Yorkshire market town of Helmsley. Close to a variety of local amenities and things to do, the house comfortably sleeps six people and provides the perfect space for a relaxing, self-catering break.

ValueLocationHiking

4.92 out of 5 average rating, 176 reviews