Cottage vacation rentals in Helmsley

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Top-rated cottage rentals in Helmsley

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Top guest favorite
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
4.87 out of 5 average rating, 139 reviews

Luxury Old Stone Cottage, Beautifully Presented

We do not accept children or 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 & York. There is free WiFi & parking plus secure storage for cycles. We have a short video Youtube@tara101 playlist The Chauffeurs Cottage

Top guest favorite
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
4.92 out of 5 average rating, 324 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 favorite
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
4.99 out of 5 average rating, 184 reviews

Historic cottage, log-burning tub & village pub

Unwind in this beautifully restored Grade II listed, 17th Century farmers cottage with exposed beams, original ironwork, underfloor heating and a soothing log burning hot tub. Opposite you'll find a cosy, dog-friendly village pub with open fires. You’ll be 7 minutes away from artisanal food producers in the market town of Malton (known as Yorkshire's Food Capital) and ideally located for exploring the Yorkshire Wolds (2 miles), Howardian Hills (10 miles), York (17 miles) & Beaches (27 miles).

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
4.99 out of 5 average rating, 127 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 Grooms Cottage is presented with its charming brick facade. A paved patio area features a table and chairs, ideal for outdoor dining. The property includes several windows and light grey doors, complementing the serene setting.
Cottage
5 out of 5 average rating, 132 reviews

Grooms Cottage by Sheriff Hutton Castle Near York

Grooms Cottage is on a private estate right next to the ruins of Sheriff Hutton Castle. The property is in a peaceful setting but only two minutes walk away from the village pub and post office/general store. Our cottage was completely renovated in 2021 and is in a great location for walkers, cyclists, and explorers. It’s about 10 miles from both York and Malton, Castle Howard is under 6 miles away, and the coast can be reached in under an hour. Grooms Cottage sleeps 4 guests+2 babies +dogs

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
4.98 out of 5 average rating, 316 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
The entrance to the barn features a charming wooden gate adorned with climbing plants, including wisteria and a yellow flowering vine. The pathway is lined with gravel, leading to the stone facade of the barn under a traditional red-tiled roof.
Cottage
4.99 out of 5 average rating, 150 reviews

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

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
4.98 out of 5 average rating, 128 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.

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
4.86 out of 5 average rating, 140 reviews

Cliff Stud Retreat, Helmsley - Cecil Cottage

Cecil cottage is A three bedroom cosy cottage set within the 220 acres Cliff Stud retreat estate, 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. The bathroom has a shower/bath & is fully refurbished and located downstairs. The cottage boasts it's own garden with fruit trees and is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

Top guest favorite
The charming exterior of the cottage is framed by a well-maintained garden featuring lush greenery and colorful flower beds. A gravel path leads to the entrance, with outdoor seating visible to one side. Bright blue skies and soft clouds create a cheerful atmosphere.
Cottage
4.99 out of 5 average rating, 188 reviews

Fabulous cottage in Coxwold, the perfect bolthole!

Braecote is a peaceful, warm, and welcoming cottage in the picture perfect village of Coxwold. With wide grass verges, honey coloured stone houses and a traditional country pub just up the road, Coxwold is one of the prettiest villages in North Yorkshire. York, Harrogate, Helmsley and Malton are close by, the North York Moors, Yorkshire Dales and east coast all within easy reach. Newburgh Priory is just up the road and Michelin starred Black Swan at Oldstead a short drive away.

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
5 out of 5 average rating, 468 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
A welcoming living space features a brick fireplace with an activelog burner, offering warmth to the room. A comfortable futon sofa is accompanied by soft pillows, while a wooden coffee table sits on a woven area rug. A wall-mounted TV is visible above a modern radiator.
Cottage
4.98 out of 5 average rating, 106 reviews

Beautifully renovated stable in Pickering

Brand new as of November 2022: The Hayloft on Eastgate is a former stable which has been newly converted and renovated into a cosy, well equipped holiday home situated in Pickering. The property sleeps up to 4 people and has everything you should need for a comfortable stay in this wonderful part of Yorkshire. The centre of Pickering, with its heritage railway, castle, eateries, shops and other amenities is a five minute walk away.

Popular amenities for Helmsley cottage rentals

Quick stats about cottage rentals in Helmsley

  • Total rentals

    30 properties

  • Nightly prices starting at

    € 112 before taxes and fees

  • Total number of reviews

    790 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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