Places to stay near Helmsley Castle

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Top-rated holiday rentals near Helmsley Castle

Guests agree: these stays 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.

4.98 out of 5 average rating, 121 reviews

Top guest favourite

A spacious outdoor deck is surrounded by greenery, featuring two Adirondack chairs and a round fire pit with a gentle flame. Potted plants add a touch of nature, while soft lighting illuminates the area, creating a cozy atmosphere for evening relaxation.

Treehouse in Richmond

The Pines Treehouse @ Treetops Hideouts

The Pines Treehouse is nestled underneath a huge oak tree sitting high above the running water of Sand Beck. Nature cocoons you and you can reach out and touch the trees, see wildlife all around you amongst the pines. With breathtaking views through the tress and across the valley you are completely private having no other accommodation on the site making this a truly unique and special experience. A great effort has gone into creating this space to allow you to simply relax and reset in nature.

4.99 out of 5 average rating, 159 reviews

Top guest favourite

A cozy suite is featured, with a spacious bed neatly made. A comfortable seating area contains a gray sofa with decorative pillows, a vintage trunk, and a piano. Natural light pours through two windows, illuminating the wooden floor and soft wall colors.

Guest suite in Nunnington

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

4.89 out of 5 average rating, 227 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.

4.98 out of 5 average rating, 235 reviews

Top guest favourite

A cozy workspace is depicted with a round wooden table and a comfortable chair. Shelves filled with books and decorative items line the walls. A small bouquet of flowers adds a touch of nature, while a warm-colored blanket drapes over another chair.

Tiny home in Heworth

York Poetree House, tiny treehouse home for one

Reconnect and wake up into nature at this unforgettable escape. Secluded treehouse with everything you need to soothe and inspire. Self cater, arrange meals provided by your host (a professional chef), or try one of the many eateries in town. Shops nearby. Your own private bathroom is situated a few yards away in the main house. You also can enjoy our beautiful garden, lily pond and friendly cat, Nina. Your hosts are always on hand to ensure a comfortable and nourishing experience.

4.97 out of 5 average rating, 326 reviews

Top guest favourite

A round glass dining table is set with a croissant, pastries, and two mugs. Black wicker chairs surround the table, positioned near sliding glass doors that open to a wooden deck and serene lakeside view surrounded by lush greenery.

Cabin in Kennythorpe

Lakeside cabin with private woodland spa

You're the only cabin on the lake. No other guests. No neighbours. Just you, woodland, and water. You'll arrive to find the lakeside sauna and copper bath on the deck and secret nooks around the edge of the woods where you can watch the sunset and the stars in front of the fire pit. Hidden near to the Howardian Hills and Yorkshire Wolds, Kingfisher Cabin @ Kingfisher and Yew is a Yorkshire Post Tourism Awards finalist and featured in Living North's top retreats.

5.0 out of 5 average rating, 119 reviews

Guest favourite

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

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set on a horse stud farm surrounded by 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.

4.86 out of 5 average rating, 154 reviews

Top guest favourite

A wooden balcony extends from the cabin, surrounded by lush greenery and tall oak trees. Sunlight filters through the leaves, creating a serene and natural ambiance. The dense forest provides a sense of seclusion, enhancing the retreat's peaceful atmosphere among the treetops.

Hut in Glaisdale

Crumbleclive Cabin

NOW REOPENED - SEPTEMBER 2026 Crumbleclive is a beautifully restored 100 year old cabin set within the dramatic backdrop of Crunkly Ghyll. The Cabin has a balcony overlooking the gorge with the River Esk rapids visible at the bottom. Surrounded by Oak trees you will feel amongst the treetops as birds gather on the branches around you and fly through the gorge below. It is perfect for couples wanting a romantic getaway to recharge the batteries!

4.98 out of 5 average rating, 373 reviews

Guest favourite

A large floor-to-ceiling window offers expansive views of the countryside and sunlight filtering through trees. A warm wooden bench is adorned with a welcoming sign and small plants. A cozy coffee table with decorative items can be seen in front, enhancing the inviting space.

Barn in Aislaby

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

4.94 out of 5 average rating, 386 reviews

Top guest favourite

Multiple paned windows frame a pleasant view of greenery and colorful trees outside. A decorative bowl and two ceramic jugs rest on the windowsill, allowing natural light to fill the space.

Flat in Helmsley

The Flat @ 2 Castlegate

Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

4.98 out of 5 average rating, 230 reviews

Guest favourite

A comfortable living room features a brown sofa and an armchair, positioned on a light brown area rug. A flat-screen TV is mounted on the wall above a decorative media console. Natural light enters through two large windows, adorned with patterned curtains.

Cottage in Helmsley

Clothes Prop Cottage, a Helmsley hideaway

Clothes Prop Cottage is located in the heart of Helmsley, just a couple of minutes walk from the shops, tea rooms, pubs and restaurants in this beautiful North Yorkshire market town. The property is available for 3 night weekend and 4 night mid week stays as well as full 7 night breaks. The property suits couples looking for a relaxing stay in the Yorkshire countryside, with their beloved pets welcome!

4.93 out of 5 average rating, 320 reviews

Top guest favourite

A handcrafted cabin is framed by lush greenery, with natural wood siding that complements its surroundings. A wooden footbridge leads up to the entrance, where large glass doors invite light and offer views of the peaceful forest.

Cabin in Old Byland

Brook- Luxury, off grid, woodland cabin by stream

The Lazy T is the perfect sanctuary to switch off, find some solitude, read that book you’ve been wanting to open for a while, forage for food, immerse yourself nature, enjoy evenings of peace and quiet- the hooting of the owls, the crackle of the fire and the babbling brook. The Lazy T focuses on bringing us back to simple pleasures that, in the right place and company, become so deeply felt.

4.98 out of 5 average rating, 161 reviews