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.

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 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.

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.

Little Owl Landpod

Set slap bang in the middle of the North York Moors, Little Owl is a truely special space to sit back, relax and soak up the magic of the moors! The Landpods are suitable for small families but we do not accept groups or parties. There are two small double beds but bedding is not provided. There is electricity in the pods and a Shepherds Hut next to them for cooking. The toilets are only short walk away and there is a fire pit to enjoy those special evenings!

Mill House Annex, Oldstead

This bolthole has been lovingly refurbished to a high standard throughout, providing guests with a comfortable and cosy home-from-home. There is a spacious bedroom with a king-size bed, a modern bathroom fitted with underfloor heating and a sperate bath and shower. The living room has a cosy log fire and large dining table. The kitchen is well appointed and kitted out to meet all your culinary needs. Take it easy at this unique and tranquil getaway.

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.

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.

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set within the 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.

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.