Family-friendly holiday rentals in Helmsley

Fairfax View - delightful annexe cottage, Gilling

Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

Central Fully Ensuite house sleeps 6 dog friendly

The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

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.

Delightful Shepherd’s Hut with creature comforts

Stay in the heart of nature in our unique hand-crafted Shepherd’s Hut combining rural simplicity with all the comforts you need to make your stay enjoyable and memorable. Situated in the heart of the Pennines, ‘The Spot’ is immersed in nature but within walking distance of rail/bus/canal access as well as the quirky town of Hebden Bridge. The perfect base for exploring the beautiful rolling hills and valleys - on foot or on wheels - or just switch off and relax on site - alpacas optional!

The Garden Room

Two renovated old buildings have been converted into a quiet, one bedroom, self contained Garden room. In the centre of Slingsby village, you are well placed to explore the beautiful surrounding areas of Yorkshire. A modern kitchen with fridge, microwave and cooker is equipped for preparing delicious meals. A wall mounted television with Netflix is available. The sleeping area hosts a double bed with wall hanging for clothes, adjacent to which is a bright shower room with heated towel rail.

York Poetree House, tiny treehouse home for one

Reconnect and wake up into nature at this unforgettable escape. Secluded treehouse with everything you need to soothe and inspire. Self cater, arrange meals provided by your host (a professional chef), or try one of the many eateries in town. Shops nearby. Your own private bathroom is situated a few yards away in the main house. You also can enjoy our beautiful garden, lily pond and friendly cat, Nina. Your hosts are always on hand to ensure a comfortable and nourishing experience.

A remote relaxing retreat with amazing views.

A cosy shepherds hut on a working hill farm, in the beautiful North York Moors National Park. Simply sit, relax, watch the birds and admire the view or explore the surrounding area. Walk from the hut or one of the local famous walks such as Cleveland Way, Wainstones, Roseberry Topping. Helmsley and Stokesley are lovely little market towns to explore or Whitby and York both within an hours drive. We only have one hut, so there is no sharing of facilities and the area is very private.

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set on a horse stud farm surrounded by 220 acres with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.

The Flat @ 2 Castlegate

Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

Garden Cottage - Peaceful in the Heart of Helmsley

A Unique Self-Catering Experience ! Stay in your own private luxury Home-from-Home private cottage, attached to our 1560-Built property opposite the Market square. Your own private entrance leads into your own Dining Room and Kitchenette area which leads into your own large separate Lounge. A well-appointed Shower Room is situated on the ground floor. Upstairs is a large Bedroom with fitted wardrobes and TV.

Clothes Prop Cottage, a Helmsley hideaway

Clothes Prop Cottage is located in the heart of Helmsley, just a couple of minutes walk from the shops, tea rooms, pubs and restaurants in this beautiful North Yorkshire market town. The property is available for 3 night weekend and 4 night mid week stays as well as full 7 night breaks. The property suits couples looking for a relaxing stay in the Yorkshire countryside, with their beloved pets welcome!