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.

Family · Value · Comfort

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!

Location · Value · Checkout

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

Location · Family · Kitchen

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.

Value · Location · Laundry

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

Location · Walkability · TV

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.

Family · Value · Sleep quality

The Courtyard Annexe (Please read all description)

Welcome to the Courtyard Annexe, part of our Georgian house, in the centre of Kirkbymoorside. We are not a self catering unit (no guest kitchen) or a rented second home but a more traditional bed and breakfast. We'll meet you upon arrival and show you to the part of our home that is your own separate, private space. We provide a 'tea and toast' breakfast, whilst other meals can be sourced in town. Bear in mind this is an old building with lots of steps. Please read the fuller description.

Family · Location · Pets

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

Location · Family · Pets

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.

Location · Value · TV

Goose End Cottage, North Yorkshire

Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

Value · Family · Solo travel

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.

Value · Family · Bathroom

Old Forge in Wrelton, North Yorkshire.

This cottage, in the village of Wrelton near Pickering, was a 19th century blacksmith's forge and has now been renovated into a delightful living space complete with fully-equipped kitchen, large living room area, bathroom with walk-in shower and a cosy bedroom located on a mezzanine floor which is reached via a spiral staircase. The Old Forge offers a great location for a relaxing stay in beautiful North Yorkshire.

Location · Family · Biking