House holiday rentals in Helmsley

Highfield Annex with off St Parking in Keldholme

Enjoy a tranquil getaway at Heather Annex! Explore the North York Moors by foot; cycle Dalby Forest’s trails or ride the iconic Pickering steam train to Whitby. Visit charming market towns like Helmsley and Kirkbymoorside. Nearby, discover TV's 'Bangers & Cash' or York. Coastal towns, Whitby & Scarborough are less than an hour away. Walk to local pubs and cafes. Return to 1/2 an acre of grounds featuring American Miniature Horses & hens. Or simply unwind on the Patio & have a peaceful stay!

Family · Value · Sleep quality

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 · Location · Access

Country Manor House - Nr Richmond North Yorkshire

No.2 West Layton Manor is part of an Historic Victorian Manor House built in 1872. The property provides the perfect setting for families and friends gathering for special occasions or holidays in beautiful North Yorkshire. The property boasts 6 kingsize bedrooms equipped with 6 full ensuite bathrooms. A further 7th bathroom is located on the ground floor. There are 3 large reception rooms, 2 open log fires, and approximately 1/2 an acre of gardens. There is private parking for 8 vehicles.

Value · Location · Hiking

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.

Location · Value · Wi-Fi

Spinney Cottage, Pateley Bridge

Spinney Cottage is a beautifully restored home located just outside the town of Pateley Bridge in Nidderdale, a short drive from the Yorkshire Dales and Harrogate. Built in 1883 and full of characterful features such as woodburning stove and exposed stone walls, the Cottage is very well equipped with BBQ, firepit, and outdoor seating. Set in 4 acres of gardens and woodland, guests can make the most of our peaceful location. Ideal for walkers, cyclists and those looking for a calming retreat.

Location · Family · Walkability

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.

Location · Value · Cleanliness

The Nest with Luxury Hot Tub

We are proud to list our second property, 'The Nest’. A brick built detached cottage with rustic modern farmhouse design a comfortable home from home experience, ideal for romantic getaways. Our luxury accommodation features cosy open plan lounge/dining area with feature brick walls with French doors leading to a private walled patio area with luxury state of the art 6-seater hot tub for your sole use, fully fitted kitchen, luxurious bathroom, elegant, panelled bedroom with king sized bed.

Location · Family · Comfort

Ski lodge style chalet with hot tub & sauna

Welcome to our one-bedroom ski lodge style chalet nestled in the picturesque Pendle countryside of Lancashire! This charming retreat offers a perfect blend of rustic charm and modern amenities, promising a memorable getaway for couples or solo travelers. Step inside and be greeted by the warm ambiance of the open fire, ideal for snuggling up after a day of outdoor adventures. For ultimate relaxation, indulge in the sauna or unwind in the bubbling hot tub under the starry night sky.

Location · Value · Nearby

Oakforge Cottage, a spacious home from home.

Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.

Value · Location · Getting around

Explore North Yorkshire. Large, stylish farmhouse

The farmhouse is a stylish, spacious, comfortable space ideal for family get togethers and group holidays. It sits in the Vale of York, between York and Harrogate with the Dales and Moors of North Yorkshire nearby. A super house for sociable evenings in; dinner by the log fire, a game of pool or drinks and table tennis on the patio during warmer months. Great local pubs and restaurants serving excellent food and a supermarket/shops a short drive away.

Location · Value · Hiking

The Shed, Hovingham, York

An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.

Family · Location · Accuracy

31 Bridge Street

This beautiful 18th century cottage sits in the heart of the lovely North Yorkshire market town of Helmsley. Close to a variety of local amenities and things to do, the house comfortably sleeps six people and provides the perfect space for a relaxing, self-catering break.

Family · Location · Check-in