Vacation rentals in Roseberry Topping

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!

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 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.

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 🤧)

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.

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.

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.

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.

Riverside Guest Annexe

Riverside guest annexe is in a secluded garden but is within 50m of Waterfall Park and Great Ayton High Green, with its shops, pubs, cafes, take-aways and Tourist Information. The annexe is attached to our house, but has its own entrance, patio, garden area and parking space. We can accommodate 2 adults comfortably, plus a third adult or up to 2 children on our pull-out and/or sofa bed. We provide bedding, towels and toiletries. No smoking or pets are permitted in the annexe.

Rural Woodland Retreat in Nature

A magical hidden gem in the heart of nature. Experience tranquility in our intimate and rural retreat, perfect for embracing simple living in an eco-friendly, enchanted woodland. Whether you seek a romantic getaway, a solo retreat, a yoga escape, or a peaceful adventure our traditional Shepherd's Hut promises an unforgettable stay. Immerse yourself in nature in this unique and peaceful setting.

Charming cozy cottage in Guisborough

The perfect base for your Yorkshire adventure. This newly renovated charming cozy cottage blends traditional 18th Century character with modern comforts. Situated in the heart of the historic market town of Guisborough, you are a short stroll from unique and independent shops, bars and eateries. Close and easy access to the North York Moors National Park and the scenic Yorkshire coast.