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.

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.

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

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.

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.

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.

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.

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!

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.