Holiday houses in Middleton-on-Leven

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Top-rated holiday rentals in Middleton-on-Leven

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

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Top Guest favourite
An exterior view of a charming self-contained apartment, featuring a red-tiled roof and rustic brick facade. A small patio area is visible, furnished with a table and chairs, surrounded by scenic countryside, under a bright blue sky with scattered clouds.
Guest suite in North Yorkshire
4.96 out of 5 average rating, 258 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 favourite
A charming blue shepherd's hut is set within a fenced grassy area, surrounded by trees. A wood-fired hot tub is positioned nearby, inviting outdoor relaxation. The entrance features wooden doors and two small windows, allowing natural light to enhance the hut's cozy appearance.
Shepherd’s hut in Potto
4.93 out of 5 average rating, 259 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 favourite
A well-lit bedroom features a spacious bed with patterned bedding, complemented by bedside lamps. A small wooden table with two chairs sits adjacent, creating a cozy dining area. Natural light streams through a skylight above, enhancing the inviting atmosphere of the room.
Condo in Stokesley
4.98 out of 5 average rating, 631 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 favourite
An open living area features a comfortable sectional sofa in a calming blue tone, paired with a natural wood table. Natural light enters through two skylights, illuminating the space with light neutral walls and a striped carpet providing a subtle contrast.
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 favourite
A charming building features wooden siding and large windows that illuminate the interior. Surrounding the structure is a well-kept garden with diverse greenery and pathways, enhancing the outdoor ambiance. The picturesque setting is complemented by a stone patio area for sitting and relaxing.
Guest suite in North Yorkshire
4.98 out of 5 average rating, 368 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.

Guest favourite
A modern wooden house is elevated on stilts, set against a backdrop of lush greenery. Large glass windows provide a view of the surroundings, while a staircase leads to the entrance. Soft clouds hover in the sky, hinting at a serene atmosphere.
Treehouse in Wingate
4.98 out of 5 average rating, 102 reviews

Couples treehouse retreat with hot tub - Nuthatch

Restatthenest. Beautifully designed in keeping with its spectacular natural surroundings, Nuthatch offers a curious combination of luxurious comfort with lavish décor. With open plan living, a super-king size bed and the added indulgence of underfloor heating and an inbuilt music system, offering guests their own private balcony and hot tub. Features • Super king bed • Fully equipped kitchen • Ensuite with rain shower • Private hot tub • Underfloor heating • Inbuilt music system • Smart TV

Top Guest favourite
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 favourite
A comfortable living area is highlighted by a brown velvet sofa and a classic armchair, complemented by a unique throw. A window dressed with patterned curtains allows natural light to fill the space, while a framed artwork and a side lamp enhance the cozy ambiance.
Cottage in Stokesley
4.98 out of 5 average rating, 115 reviews

Townhouse in Stokesley

A delightfully old, mid-terraced townhouse situated in the conservation area of West Green, Stokesley. The house has been sympathetically decorated and furnished to reflect its heritage, with a beautiful collection of traditional, upcycled and vintage inspired furniture to support independent, local businesses. We are dog friendly. Outside we have a secure, seated courtyard. Stokesley and the local area hosts all manner of restaurants and cafes, many of which are dog-friendly.

Top Guest favourite
A wooden lodge is depicted, featuring a spacious deck enclosed by a low fence. Outdoor seating arrangements are visible on the deck, with greenery surrounding the lodge. Large windows reflect natural light, enhancing the rustic charm of the structure set against a backdrop of hills.
Cabin in Middlesbrough
4.98 out of 5 average rating, 195 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 favourite
The private patio area is surrounded by lush greenery, featuring comfortable outdoor seating and a table. A modern structure is visible in the background with large windows, allowing natural light to fill the interior. The space is designed for relaxation and enjoyment.
Guesthouse in North Yorkshire
4.91 out of 5 average rating, 314 reviews

Luxury 1 bedroom lodge with hot tub and fire pit

Set in the grounds of a grade 2 listed victorian gate house, cedar lodge offers modern luxury accommodation. Inside there is a double bedroom, with King size bed, shower room and living/kitchen area. Entertainment is provided by Bang and Olufsen widescreen UHDTV including streaming services. Outside is your own private patio area with a hot tub, BBQ and wood fired fire pit Great rural location for exploring hills and moors, coastline and market towns.

Top Guest favourite
A wooden deck features steps leading up to a blue shepherd hut with a solid wooden door. Two metal chairs and a small table are set on the deck, surrounded by gravel. A folding chair is positioned nearby, with a flower box hanging by the entrance.
Shepherd’s hut in Hilton
4.97 out of 5 average rating, 117 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 favourite
A brick cottage with two stories showcases a well-maintained front garden. Two entrances are framed by small potted plants, with evenly spaced windows allowing natural light to enter. The surrounding greenery adds to the rural charm of the property.
Cottage in Northallerton
4.94 out of 5 average rating, 245 reviews

Church Cottage, West Rounton, North Yorkshire

Church Cottage is located in the small village of West Rounton, on the edge of the stunning North Yorkshire Moors. This makes it an ideal base for walkers, close to the Cleveland Way, and Mount Grace Priory. Short drives away are, York and Whitby. The quiet rural setting and fresh air, together with the cosy warmth of Church Cottage make it the perfect base for walkers, nature lovers, and for anyone looking to relax from a busy life.

Popular amenities for Middleton-on-Leven holiday rentals