Family-friendly vacation 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.

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

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!

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annex 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 Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Kilburn Chicken Cottage

Opened in 2018, dog-friendly Kilburn Chicken Cottage has been hosting guests from all over the world. With one of the highest Airbnb ratings in the area, parents and children alike have loved coming to stay to look after their own flock of hens. This 3 bedroom cottage is situated in the beautiful North Yorkshire village of Kilburn, with fast EV charging in Thirsk nearby. You're spoilt for choice when it comes to great views, great food and entertaining hens.

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.

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!