House holiday rentals in Helmsley

Find and book unique houses on Airbnb

Top-rated house rentals in Helmsley

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

1 of 1 pages1 / 1
Top guest favourite
A private hot tub is situated in a serene outdoor space, surrounded by leafy greenery. The view includes neighboring rooftops and a clear blue sky, creating a peaceful ambiance for relaxation.
Home in Welburn
4.97 out of 5 average rating, 102 reviews

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.

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
5 out of 5 average rating, 103 reviews

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!

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
4.98 out of 5 average rating, 111 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
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
4.97 out of 5 average rating, 122 reviews

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to go off grid, listen to the wildlife and enjoy the beautiful countryside. York is 20 miles away with countless tourist attractions and less than 10 minutes drive is the pretty market town of Helmsley 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.

Top guest favourite
Home in North Yorkshire
4.98 out of 5 average rating, 208 reviews

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.

Top guest favourite
The exterior of the cottage showcases a restored stone façade, with large windows allowing natural light to fill the interior. A gravel patio area is surrounded by planters, with a bench positioned nearby, providing a welcoming entry point to the home.
Home in Dacre
5 out of 5 average rating, 110 reviews

Spinney Cottage, Pateley Bridge

Spinney Cottage is a beautifully restored home located just outside the town of Pateley Bridge in Nidderdale, a short drive from the Yorkshire Dales and Harrogate. Built in 1883 and full of characterful features such as woodburning stove and exposed stone walls, the Cottage is very well equipped with BBQ, firepit, and outdoor seating. Set in 4 acres of gardens and woodland, guests can make the most of our peaceful location. Ideal for walkers, cyclists and those looking for a calming retreat.

Top guest favourite
The exterior of a rustic brick building is surrounded by lush greenery and vibrant flowering plants. A spacious wooden dining table sits on a patio, inviting outdoor meals. The entrance features double doors, framed by wisteria and climbing roses, enhancing the welcoming appeal.
Home in North Yorkshire
4.99 out of 5 average rating, 109 reviews

The Old Post Office pretty village 20min from York

The Old Post Office, providing a lovely 3 bedroom character suite, with private, off road parking and a sunny private courtyard to enjoy outside eating and relaxation.. Situated in the beautiful village of Alne, 10 miles from York and access to Harrogate, the Dales, the North York Moors and the Coast. The Area has just been awarded "one of the Best Places to Live in the UK" by The Sunday Times. Stylish, Egyptian cotton bedding on all beds and providing everything you will want for your stay.

Top guest favourite
The exterior of Granary Lodge is displayed, featuring a traditional stone façade with a red door. A sloped roof and multiple windows complement the building, surrounded by well-maintained landscaping and a gravel driveway leading to the entrance.
Home in Thirsk
4.99 out of 5 average rating, 126 reviews

Spacious two bedroom country property

Granary Lodge is situated on a quiet lane, yet less than two miles from Thirsk; a busy, attractive market town. It is spacious with a large lounge, kitchen, a double bedroom (ensuite bathroom) and a twin room. Also, a shower room with basin and toilet. Enjoy the use of your private patio seating area with views over the owners garden and pond. A larger garden area and further seating is also available for guest use. Local good pub (15 mins walk). N York Moors National Park: 15 mins drive.

Top guest favourite
A dual aspect lounge showcases large windows framing scenic countryside views. A stylish desk and chairs are set beside a low coffee table, inviting work or relaxation. The space is complemented by warm lighting and rich wooden furniture, creating a calming environment.
Home in Richmond
4.98 out of 5 average rating, 158 reviews

Treetops Cottage @ Treetops Hideouts

Treetops Cottage is a luxury country retreat just one mile from bustling Richmond nestled in a private, stunning setting. The newly refurbished property boasts exceptional far reaching views across the rolling countryside and the south facing patio is a fantastic space to watch the wild deer that come up from Sandy Beck. Ideally located alongside Brokes giving direct access to the beautiful surrounding countryside, the property offers luxury living with great days out on your doorstep.

Top guest favourite
A steam train is seen departing from a vintage railway station, with wisps of steam billowing from the engine. The station's platform is surrounded by greenery, and classic signal lights are positioned along the tracks, enhancing the historical ambiance.
Home in North Yorkshire
4.89 out of 5 average rating, 229 reviews

Short stroll to pubs, cafés & shops. Free Parking

Enjoy a clean and comfortable, cosy yet spacious, experience at this peacefully located holiday home. Just a very short stroll from Pickering town centre where you’ll be spoilt for choice with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking or free parking permit for Eastgate car park which is less than 300 meters away.

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
4.9 out of 5 average rating, 457 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.

Guest favourite
A charming stone barn features a warm terracotta roof and large windows allowing natural light to enter. The outdoor space includes a small metal table with two chairs, set on the green lawn, ideal for enjoying a pleasant morning or afternoon.
Home in Hovingham
4.9 out of 5 average rating, 261 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.

Popular amenities for house rentals in Helmsley

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 $230 SGD per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Helmsley holiday rentals include wifi 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!

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