Cottage vacation rentals in Helmsley

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Top-rated cottage rentals in Helmsley

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Top guest favorite
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, 300 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 favorite
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 favorite
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 favorite
A stone-built cottage features a rustic exterior with a traditional red-tiled roof. An inviting wooden door leads to the entrance, while large windows allow natural light to fill the interior. Two wooden wheels are positioned against the cottage, adding historical charm to the surrounding grassy area.
Cottage in Goathland
4.98 out of 5 average rating, 317 reviews

The Smithy at Cross Pipes, Goathland

The Smithy is a self contained stone built cottage situated on the edge of the beautiful North Yorkshire Moors. It was built in the 1800’s and was originally one of two blacksmiths serving the community of Goathland. The Smithy offers you a comfortable base to visit the local area. Spacious studio accommodation with a king sized bed in a recessed area, walk in shower and toilet, full kitchen facilities, wood burning stove, TV and Wi-Fi. There is an outside seating area and private parking.

Guest favorite
A charming cottage exterior is surrounded by lush greenery, featuring a stone facade and a blue front door. Tall trees and neatly trimmed bushes frame the entrance, while wildflowers and grass add a natural touch to the pathway. The peaceful setting invites exploration.
Cottage in Pickering
4.84 out of 5 average rating, 192 reviews

Cosy one bedroom cottage in Pickering

This lovely cottage is nestled in the centre of the beautiful market town of Pickering, Relax at this charming cottage which offers easy access to the enchanting landscapes of the North Yorkshire Moors and the nearby towns and coast. Whether you visit the iconic North Yorkshire Moors Railway, attend a concert at the Scarborough Open Air Theatre, or spend a day at the beach or exploring Whitby and the Moors. If you are seeking relaxation or adventure, this unique getaway is the perfect choice.

Top guest favorite
A detached holiday cottage features a red front door and distinctive round window, set against a backdrop of textured brick walls. The surrounding area is landscaped with greenery, and gravel provides off-road parking in front of the building.
Cottage in Pickering
4.93 out of 5 average rating, 358 reviews

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE

Detached holiday cottage Sleeps two (ONE DOUBLE BED) FREE WIFI Off road parking En-suite bathroom Fully equipped kitchen TV and fridge freezer Microwave Ideal location for all local attractions 2 minute walk into Pickering and local pubs, restaurants and shops Quotes from past guests: it's just perfect/best cottage we've stayed in/everything is so welcoming/ location is fantastic Places to visit in North Yorkshire http://www.iknow-yorkshire.co.uk/attractions/north_yorkshire/

Top guest favorite
An open dining area is filled with natural light from skylights and large windows. A table set for dining is surrounded by several light-colored chairs. A view of a private deck can be seen through the patio doors, accompanied by vibrant floral arrangements on the table.
Cottage in Danby
4.94 out of 5 average rating, 138 reviews

Winnow Cottage . in the Heart of the NY Moors

Winnow Cottage is set in the idyllic North York Moors National Park. Dating back to the 1800s, the cottage has an open plan living and dining area with a kitchen and two en-suite double bedrooms. Patio doors lead out to a private decked area with views of the moors. The cottage is dog-friendly, 2 dogs welcome and accessed via a 1/4 mile rough single bridle track. There are many walking and cycling routes from the cottage and it is well-situated for exploring beautiful North Yorkshire.

Top guest favorite
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, 340 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 favorite
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 favorite
The charming stone exterior of Bumble Bee Cottage showcases a welcoming front door highlighted in blue. Two dogs sit on the steps, framed by neatly arranged plants. Decorative bunting lines the entrance, enhancing the cottage's inviting appearance.
Cottage in Welburn
4.99 out of 5 average rating, 113 reviews

Luxury Cottage close to Castle Howard with hot tub

Bumble Bee Cottage, a luxury 2 bedroomed holiday home featuring a private hot tub (on request) with a large private garden. Relax & unwind in this peaceful property, set back from the road in the pretty village of Welburn in the heart of The Howardian Hills. Castle Howard is approximately 1 mile away & is walkable from Bumble Bee. Welburn has a pub/restaurant & a shop/bakery. Yorkshires Food Capital, Malton is a 5 mile drive away & the beautiful city of York only 15 🐝

Top guest favorite
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, 492 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.

Top guest favorite
The garden features neatly trimmed hedges arranged in a circular pattern, surrounded by blooming rose bushes. A sculpture stands at the center, and a person is seen tending to the greenery. Lush plants and flowering plants contribute to the serene landscape.
Cottage in Naburn
4.95 out of 5 average rating, 303 reviews

Country cottage five miles from the City of York

Naburn Grange Cottage is a farm worker’s cottage attached to an 18th century riverside farmhouse in between the villages of Naburn and Stillingfleet. With easy access to York by car, bus, cycle track or (in the summer months) riverbus, you can explore the city’s history or the beauty of the surrounding countryside. This one-bedroomed cottage is well-equipped and private, with the owners next door for information or advice on your visit.

Popular amenities for Helmsley cottage rentals

Quick stats about cottage rentals in Helmsley

  • Total vacation rentals

    Explore 30 vacation rentals in Helmsley

  • Nightly prices starting at

    Helmsley vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

  • Verified guest reviews

    Over 810 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Helmsley vacation 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!

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