Vacation rentals in Middleton-on-Leven

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Top-rated vacation rentals in Middleton-on-Leven

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

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Top guest favorite
Treehouse in Richmond
4.99 out of 5 average rating, 136 reviews

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.

Top guest favorite
Guest suite in North Yorkshire
4.96 out of 5 average rating, 256 reviews

North Yorkshire, The Beehive-countryside get-away

The Beehive is a beautiful self-contained apartment, situated on our farm, with separate access, king size bed, sofa seating area, fully equipped private kitchen, and bathroom with a bath and shower. Full off-road car-parking, and private patio area. Situated in the countryside directly onto a Bridleway, only 0.5m away from the stunning Hutton Rudby Village surrounded by views of the Cleveland Hills, Captain Cooks Monument and Roseberry Topping. Perfect for walking, cycling or just relaxing.

Top guest favorite
A wood-fired hot tub is positioned on a wooden deck, overlooking expansive green fields. The grassy landscape extends into the distance, framed by rolling hills under a cloudy sky.
Shepherd’s hut in Potto
4.93 out of 5 average rating, 257 reviews

Honeysuckle Shepherd’s Hut w/ Hot Tub and T/court

Off Grid shepherd’s hut with a wood fired hot tub and tennis court in the picturesque village of Potto, near Swainby. The perfect weekend getaway for 2 with stunning views of the North Yorks moors and a wood burner. This hut is cosy, warm and comfortable. The shepherd’s hut has a hot shower, working gas stove and a mini fridge. There’s a separate private composting loo. And during the summer you may use the tennis court just a short walk through the orchard. There is no electricity in the hut.

Top guest favorite
A dining table is set with elegant glassware and white dishware, complemented by a textured runner. A bottle of champagne sits prominently, alongside a lit candle. Large windows provide a view of the garden, inviting natural light into the space.
Cottage in Stokesley
4.91 out of 5 average rating, 315 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
Condo in Stokesley
4.98 out of 5 average rating, 628 reviews

Mabel Cottage - Stay in the heart of Stokesley

This charming cottage in the heart of Stokesley is the perfect retreat, with pubs, cafes, shops, and supermarkets all within walking distance. Enjoy an equipped kitchen, shower room, a Harrison (made in Yorkshire) king size bed, dining area and T.V . Ideally located, you’re just a short drive from North York Moors National Park, Roseberry Topping, Whitby’s historic seaside charm and more. Whether exploring or unwinding, this cottage offers everything you need for a memorable Yorkshire getaway.

Guest favorite
The exterior of the house is adorned with a white facade, complemented by grey roofing and decorative eaves. A spacious driveway leads to two garage doors with ample parking space. A wooden bench is situated near the entrance, inviting visitors to relax.
Home in Marton-in-Cleveland
4.95 out of 5 average rating, 130 reviews

‘The Penthouse’

This modern place to stay is perfect for anyone visiting the area;professionals,families&friends alike.Spread across the top floor of one of the largest houses in Marton,with it’s own guest entrance,it offers space,security&privacy. ‘The Penthouse’ comprises of2double bedrooms,a bathroom&open living area.There is also the option to turn a double room into a twin for flexibility. It has its own fridge,kettle,tea&coffee,workspace, TV&access to a utility(m’wave,toaster,airfryer,hob) for cooking.

Top guest favorite
Guest suite in North Yorkshire
4.98 out of 5 average rating, 366 reviews

*The Vicarage Annexe, Carlton, North Yorks 1BR S/C

The Vicarage Annexe is a beautiful, one double-bedroom facility situated at the foot of the Cleveland Hills. The building was originally built as a prayer and study room for the Vicarage. This is now a self-contained living area with en-suite facilities. The Annexe is located in the picturesque village of Carlton-in-Cleveland, which is in the North Yorkshire Moors National Park and this is an ideal location for a couple who enjoy the countryside for relaxing, sightseeing, walking or cycling.

Top guest favorite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny home in Urra
4.98 out of 5 average rating, 235 reviews

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annexe is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annexe dates back to the 16th century and is full of charm. You can walk from our Annexe straight up onto the Cleveland way where you can walk or bike for miles. Our Annexe is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Top guest favorite
The entrance to the wooden lodge features a welcoming set of steps leading to the main door. Colorful flower pots are placed by the doorway, and a lush grassy area extends towards rolling hills in the background under a clear blue sky.
Cabin in Middlesbrough
4.98 out of 5 average rating, 194 reviews

The Lodge at Viewley Hill Farm

Viewley Hill Farm Lodge is a spacious and comfortable 3 bedroomed wooden lodge on a working farm. Situated in a peaceful and idyllic setting, the lodge has stunning views of the North York Moors and the Cleveland Hills. Guests can enjoy a range of walks in the local area including some that can be accessed directly from the farm. The local area boasts not only fabulous countryside but also easy access to the glorious north east coast and a wide variety of visitors attractions.

Top guest favorite
A rustic wooden door with a small window opens onto the shepherd hut's decking area. The door features a black handle and latch, while a hanging planter with purple flowers adds a touch of nature. The surrounding countryside is visible in the background.
Shepherd’s hut in Hilton
4.97 out of 5 average rating, 116 reviews

Swallow's Nest, Shepherd Hut, Family Farm Location

Swallow’s Nest, Shepherd Hut is an oasis of peace and quiet on its own tranquil garth setting, commanding beautiful views of the majestic Cleveland hills. We guarantee a stress free, relaxing stay on our wonderful family arable farm, surrounded by our lovely horses. Guests to Swallow's Nest will benefit from open countryside and lots of fresh air. Sit quietly overlooking the field wildlife pond to view a mixed variety of birds visiting the area.

Top guest favorite
The exterior features a contemporary wood-clad structure with large glass doors and a sloped roof. A set of stone steps leads to the entrance, while natural stone and wooden elements create a harmonious look. Surrounding greenery enhances the overall setting.
Farm stay in Harrogate
4.98 out of 5 average rating, 317 reviews

Springhill Studio, Brimham Rocks Yorkshire Dales

A unique and romantic larch-clad studio with stunning views over Nidderdale, just a mile from Brimham Rocks. Once jeweller Alice Clarke’s creative space, it now offers a peaceful, stylish retreat with a hanging log burner and on-site parking. Set above our other Airbnb, Cosy Cottage, both spaces run on renewable energy. We’re excited to share this special place with those seeking a tranquil escape in the heart of Yorkshire.

Top guest favorite
Vacation home in Middlesbrough
4.96 out of 5 average rating, 134 reviews

Bluebells Cottage, Urra nr Chop Gate, N Yorkshire.

Luxury romantic Yorkshire cottage retreat in the North Yorkshire Moors National Park nestled next to a bluebell wood with a babbling brook and direct access out into the most beautiful countryside. Close to the beautiful historic market towns of Helmsley and Stokesley and 10 minutes from James Cook's village of Great Ayton. Day trip distance to the seaside fishing villages of Whitby, Staithes and Robin Hoods bay.

Popular amenities for Middleton-on-Leven vacation rentals