Family-friendly holiday rentals in Helmsley

Boutique Shepherd’s Hut & Alpaca Experience

Wake up in a luxury shepherd’s hut in the hills around Hebden Bridge, and start your morning feeding friendly alpacas right outside your door. Hand-crafted and thoughtfully designed, ‘The Spot’ offers a boutique countryside escape - perfect for couples looking to switch off, unwind, and enjoy something a little different. A nature retreat yet within easy reach of Hebden Bridge’s independent shops, cafes and walks, you get the best of both worlds: peaceful seclusion with lots to explore nearby.

Indoor spaces · Family · Barbecue

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.

Family · Indoor spaces · Check-in

Pretty Yorkshire Stone Cottage Harome

A charming stone cottage situated in the picturesque village of Harome, 3 miles from the market town of Helmsley.This characterful cottage is up to date with everything you need without losing original features of beamed ceilings & a cosy log burner. The cottage offers luxe accommodation with a spacious kitchen, two delightful bedrooms, a power shower, bath, well equipped kitchen & hotel grade linen. A cosy sitting room with open plan dining area. There is a little garden outside with a table.

Family · Indoor spaces · Nearby

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.

Indoor spaces · Kitchen · Hiking

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to relax, listen to the wildlife and enjoy the beautiful countryside. The pretty market town Helmsley is less than 10 minutes drive, with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants. York is 45 mins drive and an hour to the coast for beach walks.

Indoor spaces · Family · Walkability

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.

Kitchen · Indoor spaces · Hiking

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.

Family · Kitchen · Parking

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.

Indoor spaces · Kitchen · Comfort

Cliff Stud Retreat, Helmsley, Frankel Cottage

Book Direct - 15% saving - Cliff Stud Retreat Frankel 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 woodburner and enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.

Kitchen · Family · Decor

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!

Indoor spaces · Kitchen · Outdoor spaces

Brook- Luxury, off grid, woodland cabin by stream

The Lazy T is the perfect sanctuary to switch off, find some solitude, read that book you’ve been wanting to open for a while, forage for food, immerse yourself nature, enjoy evenings of peace and quiet- the hooting of the owls, the crackle of the fire and the babbling brook. The Lazy T focuses on bringing us back to simple pleasures that, in the right place and company, become so deeply felt.

Kitchen · Indoor spaces · Access

Lovely self-contained hillside village Annexe

During Covid we follow government advice: if movement restrictions are reintroduced, we offer a full refund for your stay. We are committed to following AirBnB's enhanced cleaning and disinfecting protocol. On arrival, guests check themselves into completely self-contained accommodation. We will do everything in our power to ensure the safety and comfort of our guests.

Kitchen · Family · Amenities