Holiday rentals 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
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
4.99 out of 5 average rating, 151 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 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
4.96 out of 5 average rating, 265 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.

Guest favourite
The exterior of a modern cabin features dark wood paneling and large windows. A set of steps leads up to the entrance, and the surrounding area has been landscaped with gravel and wooden edging, showcasing a neat and tidy presentation.
Cabin
4.92 out of 5 average rating, 130 reviews

Moor View Luxury Log cabins

The whole group will enjoy easy access to everything from this centrally located place. Nestled below the Cleveland Way and at the bottom of the with sunken in hot tub/spa these brand new luxury cabins are full of luxury what you would expect, 2 bedrooms that sleep 4 with large full bathroom and en-suite, each room having its own dressing room, dishwasher and washer/dryer, spacious and comfortable. Situated in open field with lovely views. Within a village setting with pubs and restaurants here

Top guest favourite
The exterior of a hand-renovated railway carriage is displayed, accompanied by a private garden area featuring a fire pit, seating, and a unique egg chair. Green grass surrounds the structure, with a clear sky overhead and soft cloud formations visible in the background.
Shepherd’s hut
5 out of 5 average rating, 116 reviews

Railway Carriage Hideaway

A beautiful hand-renovated 1960s railway carriage, nestled in a quiet rural farm in Norton le Clay, North Yorkshire. Featuring bespoke detail throughout, our unique hideaway features a luxurious double bed with TV, a fully equipped kitchen, bathroom with shower, and a cosy log burner. Outside, enjoy the fenced private space with a fire pit/BBQ, games and seating overlooking the iconic White Horse. Tucked behind a wildflower bank with its own track and parking, this is a peaceful spot to unwind.

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
4.93 out of 5 average rating, 283 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
Apartment
5 out of 5 average rating, 38 reviews

Luxury, Romantic Bolt Hole, Don’t Miss This One …

Maple House Retreat, prepare to be WOWED…think plush pillows that hug you back, luxury robes, roll top bath, coffee station & fridge with sweet treats, & a cozy nook with floor to ceiling panoramic windows boasting gorgeous countryside views, just begging you to curl up with a good book, a glass of wine & a Netflix binge – No judgement here! Cozy pub 2 minutes stroll, & fabulous eateries close by. A peaceful, luxury air conditioned haven to relax! Celebrating? You just found the perfect stay!

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.
Apartment
4.98 out of 5 average rating, 653 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.

Top 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
4.96 out of 5 average rating, 141 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
4.98 out of 5 average rating, 392 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 favourite
Place to stay
4.98 out of 5 average rating, 273 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
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.
Guest house
4.91 out of 5 average rating, 326 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
4.98 out of 5 average rating, 126 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.

Popular amenities for Middleton-on-Leven holiday rentals