Holiday houses in Roseberry Topping

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Top-rated holiday rentals in Roseberry Topping

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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, 273 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 charming cottage with a red-tiled roof is situated alongside a pebbled pathway. The inviting exterior features a mix of brick and stone finishes, with white-framed windows. Adjacent, a historic stone church with a tower is visible, creating a serene backdrop amidst a well-maintained garden.
Cottage in Carlton-in-Cleveland
4.97 out of 5 average rating, 176 reviews

Old Fire Station Cottage | EV Charger | Opt 2nd BR

Contemporary Comfort in a Charming Cottage – Carlton-in-Cleveland, North York Moors National Park. Perfect for a quiet escape or an active adventure, this beautiful cottage offers everything you need Fast, reliable Wi-Fi & Smart TV Welcome goodies: fresh milk, coffee, sugar, tea, and delicious homemade cake Just a short stroll away, enjoy authentic Thai cuisine and top-notch real ales at the friendly village pub, The Blackwell Ox – also offering excellent takeaway options. EV Charger by App

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, 645 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
A terrace features a round table set for two, accompanied by stylish woven chairs. A view of the lush green valley and surrounding trees creates a serene backdrop, while a small barbecue grill stands nearby on the stone surface.
Farm stay in Hartoft
5 out of 5 average rating, 152 reviews

Storey Corner - Where memories are made

Set on the side of a picturesque valley in the small hamlet of Hartoft Storey Corner is a private self contained wing of Storey House that makes for a relaxing, quiet, luxury retreat away from the hustle and bustle. Private Hot tub (new for 2026) Quiet location situated in the North York Moors national Park. An area of outstanding beauty and in the International Dark Skies area. Great for star gazing Perfect for couples Pickering, Whitby, Helmsley York and the coast are all within easy reach

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, 381 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
The image captures a shepherd's hut nestled in a lush green landscape. A wooden bridge crosses a stream, leading to an open field. The surroundings are complemented by mature trees and distant structures, suggesting a serene and private setting.
Shepherd’s hut in Great Ayton
5 out of 5 average rating, 143 reviews

North Yorkshire Shepherds Hut Great Ayton

Great Ayton TS96HY. The Yorkshireman is situated in a Quiet and restful position close to the hills for walks. Clean and comfortable, the Shepherds Hut is near to Great Ayton, the childhood home of Captain Cook, with lovely tea rooms and friendly villagers. It's a 10 minutes drive is the North Yorkshire Moors gateway which will lead you to Whitby. (Our apologies but with a heavy heart we decided not to allow dogs as it is such a small space and we have to consider other guests allergies 🤧)

Top Guest favourite
A gravel pathway leads gently through a lush green lawn towards 'The Highlander' pod, framed by trees and bushes. Soft lighting fixtures line the pathway, guiding guests to the entrance of the cabin, nestled in a serene natural setting.
Cabin in Ugthorpe
4.98 out of 5 average rating, 259 reviews

The Highlander

Welcome to Lawns Farm Luxurious Glamping accommodation in an idyllic location. Here at Lawns Farm Glamping, ‘The Highlander’ is a perfect romantic retreat for couples, or a fun family getaway. Sandsend Beach is only four miles away and Runswick Bay three which offer some great local dining treats. Whitby is the local town approx a fifteen minutes drive. With ‘The Highlander’ offering a luxurious hot tub it’s the perfect stay! (Bookings are available without the hot tub, please get in touch).

Top Guest favourite
A living area features a comfortable couch adorned with decorative pillows and a single armchair beside a bright window. A simple coffee table rests on a textured rug, completing the cozy ambiance of the space.
Cottage in Great Ayton
4.98 out of 5 average rating, 110 reviews

Bumble Cottage. Lovely 2 bedroom Edwardian cottage

Bumble cottage is a beautiful family and dog friendly holiday home. Only a short walk from the centre of the village. Great Ayton is situated on the edge of the North Yorkshire moors and provides a wonderful base for exploring the local area. There are many possibilities for family activities, for walking, hiking, road and mountain biking and running. The beautiful beach at Saltburn is also only a 15 minute drive away. There are several excellent and unique cafes, restaurants and bars.

Top Guest favourite
An intricately carved wooden screen serves as a striking headboard behind a spacious bed adorned with decorative pillows. A warm lamp with a patterned shade stands on a small side table, while curtains with a rich design frame the window, adding a cozy touch.
Condo in Great Ayton
5 out of 5 average rating, 105 reviews

Intimate courtyard first floor accommodation

The Old Joiners Workshop is situated within the beautiful North Yorkshire village of Great Ayton which boasts many eateries and pubs. The perfect place to explore town, coast and country. Our unique accommodation has a style all of its own. Tucked away off the main High Street and nestled within a courtyard setting, guests climb a spiral staircase to their place of stay. Entering an open plan kitchen/ lounge which leads directly to the double bedroom and en-suite. Cosy and intimate.

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.
Place to stay in Urra
4.98 out of 5 average rating, 263 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 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 North Yorkshire
4.98 out of 5 average rating, 363 reviews

Crumbleclive Cabin

Crumbleclive is a beautifully restored 100 year old cabin set within the dramatic backdrop of Crunkly Ghyll. It was originally the ‘Gun Room’ for the local estate in the 1890s! 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!

Top Guest favourite
Barn in Moorsholm
4.97 out of 5 average rating, 120 reviews

Hillock's Farm Cottage, luxury

Welcome to our outstanding luxury holiday cottage nestled in the charming village of Moorsholm, Cleveland. This outstanding barn conversion offers a serene escape for couples seeking tranquility and comfort. As you step into this exquisite retreat, you're greeted by the spaciousness of the open plan layout, featuring a magnificent fully equipped kitchen, dining area, and beautiful living room with large fire place. The expansive design creates a sense of freedom and relaxation.

Popular amenities for Roseberry Topping holiday rentals