Vacation rentals in Gillamoor

The Pines Treehouse @ Treetops Hideouts

The Pines Treehouse is nestled underneath a huge oak tree sitting high above the running water of Sand Beck. Nature cocoons you and you can reach out and touch the trees, see wildlife all around you amongst the pines. With breathtaking views through the tress and across the valley you are completely private having no other accommodation on the site making this a truly unique and special experience. A great effort has gone into creating this space to allow you to simply relax and reset in nature.

Highfield Annex with off St Parking in Keldholme

Enjoy a tranquil getaway at Heather Annex! Explore the North York Moors by foot; cycle Dalby Forest’s trails or ride the iconic Pickering steam train to Whitby. Visit charming market towns like Helmsley and Kirkbymoorside. Nearby, discover TV's 'Bangers & Cash' or York. Coastal towns, Whitby & Scarborough are less than an hour away. Walk to local pubs and cafes. Return to 1/2 an acre of grounds featuring American Miniature Horses & hens. Or simply unwind on the Patio & have a peaceful stay!

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

Gorgeous country cottage, Nawton near Helmsley

A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

Easy Stroll To Pubs, Shops And Cafés

Situated on the doorstep of the North York Moors National Park, nestled less than 1 mile from the Market town of Kirkbymoorside you’ll find Pheasant Cottage. A charming, 2 bedroom, double fronted cottage that’s both cosy for 2 & spacious enough for 4. 2 king size bedrooms where the second can be made up into two singles, this holiday home suits couples, friends & families. Boasting a fabulous open fire in the kitchen diner, fully enclosed front & back garden, 50” smart tv, WiFi & parking

Couple's Bothy near Helmsley in the National Park

Unwind at this unique and tranquil getaway. Our converted barn offers a cosy, self-catering retreat for two with a woodfired hot tub, on our remote, but accessible farm in the North York Moors National Park. The Bothy is a self-contained, open space providing king sized bed, ensuite, kitchen, sitting area, outside terrace sun trap & free WiFi. The Bothy has been completed to an exceptionally high standard combining beautiful detailing and practicality. A great location for walking & cycling.

Primrose Hill Farmhouse

Primrose Hill Farmhouse is situated in the famous village of Hutton le Hole know for its picturesque setting, with traditional stone buildings and a beautiful stream running through the centre of the village. It is also home to the Ryedale Folk Museum which showcases the history and culture of the area. The cottage offers the perfect location to enjoy walking with your dogs or cycling in the North York Moors and also to explore the nearby coast line including Whitby and Scarborough

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.

The Coppice Cabin @ Helmsley Meadows

Escape to Coppice, one of four individually designed adults-only cabins at Helmsley Meadows, each with its own unique character—including one with a private sauna and freestanding bath. Created for couples and their dog, Coppice pairs warm, nature-inspired interiors with a bespoke handmade kitchen, private wood-fired hot tub and BBQ firepit. Wander into Helmsley or explore the North York Moors before relaxing beneath star-filled skies. One well-behaved dog welcome.

Luxury Old Stone Cottage, Beautifully Presented

Adults Only. No pets. The Old Chauffeurs Cottage, beautiful, luxurious, warm and cosy. Discounts for stays of 5 nights or more, please ask. Two bedrooms with comfortable King size beds and a great lounge and kitchen. A downstairs toilet & full bathroom upstairs. It provides a good base for walkers & sightseers as we are close to the North York Moors, the steam railway at Pickering & Castle Howard Free WiFi & parking plus secure storage for cycles.

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

Luxury Shepherd’s Hut with Hot Tub & Valley Views!

When the hot tub begins to steam and the sky turns pink over the valley, the world feels miles away. Tucked into the Scarborough countryside with distant sea views, this luxury Scandinavian-style shepherd’s hut is made for slow mornings, outdoor cooking and cosy movie nights under the projector. End your evening by the fire pit, toasting marshmallows beneath the stars - a romantic escape designed for switching off together.