Vacation rentals in Roseberry Topping

Saltburn l The Outlook- Sea views, Dog friendly.

This design award winning detached property is surrounded by grounds which include a slope which may not be suitable for very young children. With stunning sea views, The Outlook is built into the hillside, access is via steps down from the road (or can be accessed via a steep path). Minutes from the Valley Gardens, on the beach path, close to the town centre; this is a beautiful spot. The Outlook sadly doesn’t lend itself well to those with mobility issues or very young children. Dog friendly.

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

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.

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

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.

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

‘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.

Old Police Terrace - 3 Bed & Hot Tub Great Ayton

Exceptional 3 bed holiday cottage with HOT TUB, part of the Old Police Properties portfolio. Relax in luxury in this simply stunning period townhouse which sleeps 6. Features 3 bedrooms (2 king & 1 double bunk), log burner, bathroom essentials, bedroom comforts, on street car parking, Smart TVs, WiFi & outside seating. Experience the Cleveland hills, views of Roseberry Topping, stargaze through our telescope on the top floor bedroom balcony or take a bubbly soak in our outdoor hot tub.

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.

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!

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.

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.