Cottage holiday rentals in Helmsley

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Helmsley

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

%{current} / %{total}1 / 1
Top Guest favourite
The entrance of a cottage is framed by lush greenery, showcasing a classic stone facade with large, textured stones. A decorative gray front door is highlighted by white pediments, flanked by two windows that allow natural light into the space.
Cottage in Harrogate
4.99 out of 5 average rating, 268 reviews

The Old Coach House, in Harrogate, Sleeps 4

Centrally-located cottage, walking distance to Harrogate town centre. Recently refurbished. 2 bedrooms, 1 king & 2 singles (2'6"). Shower room. Kitchen with dishwasher, large fridge/freezer and washer/dryer. Terraces, giving you morning, afternoon and evening sun (Weather permitting). Lovely view over the historical St Luke's Court Church. Array of restaurants and bars & shops in walking distance. 7mins walk to Harrogate's Convention Centre. Quiet on street parking with disk/permit provided.

Guest favourite
The kitchen area is designed with a wood countertop and light cabinetry. A sink is located beside a window that allows natural light to illuminate the space. Fresh greenery is positioned on the sill, and neatly arranged utensils and containers enhance the organized ambiance.
Cottage in Pickering
4.82 out of 5 average rating, 306 reviews

Cosy ‘Cobblers Cottage’ - Pickering

Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.

Top Guest favourite
The cottage is constructed of traditional stone, showcasing a quaint exterior with a pitched roof and chimney. Two large windows with flower boxes frame the entrance, which features a light-colored door. The surroundings include a peaceful street lined with other characterful buildings.
Cottage in Pickering
4.91 out of 5 average rating, 350 reviews

Cosy character cottage in heart of Pickering

31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Top Guest favourite
A cozy sitting room is presented with a large mirror reflecting warm light from a chandelier. A television is positioned across from a log burner, surrounded by two armchairs and a comfortable sofa. Soft gray tones and decorative cushions contribute to the welcoming ambiance.
Cottage in Stokesley
4.91 out of 5 average rating, 299 reviews

Apple Tree Cottage. Stokesley.North Yorkshire.

A delightful old cottage overlooking West Green with a mix of antique, upcycled and vintage inspired decoration. The cottage is dog friendly, with a patio and large enclosed, secure garden. Located on the outskirts of the historic market town. The town has a distinguished wide cobbled high street lined with Georgian and Victorian buildings. It is served by banks,shops, up market restaurants and pubs. Surrounded by the Yorkshire Moors it makes an ideal base for exploring the Dales & East coast.

Top Guest favourite
The exterior of Manor House Cottage is framed by lush greenery and colorful flower beds. A well-kept lawn stretches in front, leading to the brick facade of the cottage, which features multiple windows and a welcoming entrance surrounded by trees.
Cottage in Thirsk
4.99 out of 5 average rating, 137 reviews

Manor House Cottage self catering rural location

Manor House Cottage is located in the small hamlet of Holme-On-Swale 7 miles from the market town of Thirsk which is known for its connection to James Herriott and within easy reach of North Yorkshires National Parks. Set within the grounds of the Manor House, It is a quirky upside down cottage with a well appointed modern kitchen, two bedrooms and bathroom on the ground floor with sitting room upstairs, private garden with table and chairs. There are no other holiday cottages in the grounds.

Top 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 in Ampleforth
4.98 out of 5 average rating, 330 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
The charming brick cottage features a traditional red-tiled roof and white-framed windows. Lush greenery surrounds the property, with a small garden area visible in the foreground. A wooden gate leads to the entrance, giving a sense of privacy in this tranquil setting.
Cottage in Sessay
4.96 out of 5 average rating, 339 reviews

The Cobbler's Cottage

Nestled in the scenic North Yorkshire village of Sessay, this charming former cobbler's cottage offers a spacious retreat. Inside, you'll find a wood-burning stove, TV, Blu-ray player, and a modern kitchen equipped with an oven, microwave, dishwasher, fridge freezer, Nespresso coffee maker, and a washing machine. Step outside to a private patio complete with a dining area and barbecue. Plus, we warmly welcome one well-behaved pet, so you can bring your furry friend along if you desire.

Top Guest favourite
The exterior of the cottage displays a traditional stone facade complemented by a slate roof. Multiple windows allow ample light to enter, while the gravel pathway leads to an entrance adorned with decorative plants. Sunlight bathes the building, enhancing its inviting appearance.
Cottage in North Yorkshire
4.88 out of 5 average rating, 150 reviews

Luxury Old Stone Cottage, Beautifully Presented

Adults Only. No 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 Free WiFi & parking plus secure storage for cycles. We have a short video (copy & past) Youtube@tara101 playlist The Chauffeurs Cottage

Top Guest favourite
A scenic view of a cottage by the River Seven is presented, with a backdrop of lush greenery and blooming daffodils adorning the riverbank. The charming stone building features a red-tiled roof and multiple windows reflecting the serene countryside.
Cottage in Sinnington
4.98 out of 5 average rating, 135 reviews

Goose End Cottage, North Yorkshire

Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

Top Guest favourite
A charming bedside table is positioned next to a spacious bed, featuring an antique scale as a unique lamp. The textured sandstone wall provides a warm backdrop, complementing the soft hues of the furniture and bedding.
Cottage in Burythorpe
4.97 out of 5 average rating, 199 reviews

Historic cottage, wood-fired hot tub + village pub

Three hundred year old sandstone, exposed timber beams, and the kind of warmth that comes from old walls, open fires and underfloor heating. Yew Tree Cottage @ Kingfisher and Yew sits opposite a dog-friendly village pub. Take long walks from the front door. Light the wood-fired hot tub in the walled garden and toast your toes by the fire. This Grade II listed cottage is seven minutes from the market town of Malton. Featured in Living North's top self catering retreats.

Top Guest favourite
A cozy lounge area is adorned with patterned curtains and a large sofa, complemented by decorative pillows. A wall-mounted television displays a fireplace image, adding warmth. Glass bi-fold doors open to a deck with views of surrounding greenery, creating a harmonious indoor-outdoor connection.
Cottage in York
5 out of 5 average rating, 491 reviews

Whootin Owl Barn

Whootin Owl Barn is a smart luxury detached barn with private screened hot tub and gravelled fire pit area overlooking private woodland on a tranquil country lane in the heart of North Yorkshire only 9 miles from Castle Howard and 30 mins from York City Centre. 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.

Superhost
A cozy living room features a light wooden floor and a plush red area rug. A comfortable sofa is complemented by an armchair, with a coffee table positioned centrally. Artwork adorns the walls, and a modern fireplace sits at one corner. Natural light brightens the space.
Cottage in Helmsley
4.86 out of 5 average rating, 146 reviews

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set within the 220 acres with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.

Popular amenities for Helmsley cottage rentals

Quick stats about cottage rentals in Helmsley

  • Total holiday rentals

    Explore 30 holiday rentals in Helmsley

  • Nightly prices starting at

    Helmsley holiday rentals start at $156 AUD per night before taxes and fees

  • Verified guest reviews

    Over 810 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Helmsley holiday rentals include Wi-Fi 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
  6. Cottage rentals