Vacation rentals in Roseberry Topping

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Top-rated vacation rentals in Roseberry Topping

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Top guest favorite
The stone cottage exterior showcases charming details, including a wooden door painted in soft blue. Flower pots filled with pink and white blooms adorn the entrance, enhancing the inviting appeal of the home. A small window is framed by additional greenery.
Cottage in Castleton
4.96 out of 5 average rating, 279 reviews

Cheerful & Quaint 18th Century cottage

Pretty cottage situated on the village green in the heart of Castleton village. Open fire for creating a cosy night in & perfect for exploring the beautiful North Yorkshire Moors. Castleton is lucky to have two great pubs The Downe Arms with fabulous food and atmosphere right across the road and The Eskdale which serves lovely ‘fine dining food’ but also lovely just for a drink. There’s the Old Chapel Tearoom, a Londis & ‘Off the Scale’ shop We are also along the Esk Valley train line to Whitby

Top guest favorite
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
4.94 out of 5 average rating, 267 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
Shepherd’s hut in Pinchinthorpe
5 out of 5 average rating, 10 reviews

The Whisky Parlour, Roseberry Retreat

This adult only escape is perfectly placed, over the road from the North York Moors National Park, with spectacular views of the iconic National Trust Roseberry Topping and Guisborough Forest. Ideal for the Cleveland Way or Coast. Surrounded by countryside, you can fully immerse yourself in nature whilst being a mere 5 minute drive from the busy market town of Guisborough and quaint village of Great Ayton. The heart of the countryside...but with the option of an uber into town and a takeaway!

Top guest favorite
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, 642 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 favorite
A self-contained studio apartment features a spacious bed with light blue bedding. A dining table with black chairs is positioned near a window that offers views of the countryside. The well-equipped kitchen is visible, with modern appliances and counter space.
Apartment in Stokesley
5 out of 5 average rating, 346 reviews

The Studio, near Stokesley

Our self-contained studio apartment has a shower room, store room, well equipped kitchen, superking bed ( Available as 2x3ft. singles if required), a terrace & garden overlooking open countryside with uninterrupted views of the Cleveland Hills & Captain Cook's Monument. It is a 3 min drive/15min walk to the bustling town of Stokesley where there are restaurants, cafes, pubs, shops, supermarkets, take-aways, a weekly Friday market and a popular Farmers' Market on the 1st Saturday of the month.

Guest favorite
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
4.96 out of 5 average rating, 135 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
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, 104 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

Superhost
The exterior view of the cottage features a blend of brick and white-painted surfaces. Large windows provide ample natural light. A front door, highlighted with decorative features, is flanked by planters. The quiet street showcases marked paving and distinct yellow lines.
Cottage in Guisborough
4.84 out of 5 average rating, 300 reviews

Cosy, 2 Bedroom Cottage in Guisborough Town Centre

A cosy cottage in the heart of Guisborough town centre with easy access to local shops and a large supermarket minutes away. The property is the ideal location for exploring North Yorkshire. 15 to 30 mins from the North Yorkshire Moors, Redcar and Saltburn beaches, Roseberry topping and Whitby. It’s ideal for family breaks, mini breaks and perfect for walkers. A free 2 hour high street parking disk is provided, plus free parking 6pm till 8am daily. Other times up to £4 a day.

Top guest favorite
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, 359 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 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.
Place to stay in Urra
4.98 out of 5 average rating, 251 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
A luxurious shepherd hut is set amidst a vibrant meadow filled with wildflowers. The exterior of the hut reflects natural wood tones, and a wooden deck extends from the entrance, blending harmoniously with the surrounding landscape of fields and trees.
Shepherd’s hut in Great Ayton
4.97 out of 5 average rating, 263 reviews

Hare luxury Shepherd Hut & private hot tub

Award winning luxury Shepherd hut in a beautiful location with breath taking views. Located within the North York Moors National Park, flanked by protected woodland and open views of fields and hills. Offering a peaceful retreat on the edge of a working farm, with lots of luxurious extras including goodie hamper, fluffy towels, robes and slippers for your stay. Park up the car, chill out and relax. A luxury hot tub awaits, pop open the bubbly, sit back and watch the sun go down.

Top guest favorite
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
4.97 out of 5 average rating, 152 reviews

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.

Popular amenities for Roseberry Topping vacation rentals