Family-friendly holiday rentals in Guisborough

Rose Garden Cottage, Guisborough.

Our luxuriously cosy little cottage has everything you could wish for after a day exploring the nearby woods, adjacent North Yorkshire Moors or easily accessed coast. Perhaps a relaxing soak in the feature double ended bath? You can cosy up in front of the log burning stove or step out for something to eat and drink at one of the local bars and restaurants. If you prefer to cook, the kitchen has all you need. The cottage has been renovated throughout with a feature mezzanine bed and bath suite.

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

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

Hillfoot Cottage - charming country character.

Hillfoot Cottage is a cosy and comfortable 350 yr old cottage which began life as a pig sty in the quiet country village of Yearby, near Redcar. Offering peace and tranquility with local walks on your doorstep. Located a short drive to the seaside town of Redcar and Market town of Guisborough, within 1/2 hours drive to the North York Moors National Park and Whitby and within 1 hours drive to the Yorkshire Dales. An abundance of wild birds are to be found in the gardens of our cottage.

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.

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.

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.

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.

The Beehive, modern two-bed, close to town centre

A cheerful and relaxing terrace, located a stones throw from Guisborough town centre and within close and easy access to both the North Yorkshire Moors and the Yorkshire coast. The town itself has array of shops, pubs and restaurants for you to enjoy and explore. Newly renovated to a high standard with modern fixtures, The Beehive is equipped with everything you need to have an enjoyable and cozy stay in North Yorkshire. The house is decorated for Christmas period.

Saltburn Self Catering - Treetops

<p>This property is composed of a large open plan living space, balcony and kitchen on the ground floor. The lower ground floor includes two large bedrooms, two bathrooms and doors to an outside terrace space. Above the ground floor which includes seating and beautiful sea views. There is also a double sofa bed in the living room, allowing upto 6 guests. This property is dog friendly , there is an additional charge of &pound;25 per stay.</p>

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.