Self Catering Holiday Cottages in Helmsley

Enjoy the beauty of the North York Moors National Park from the comfort of Ryedale Cottage. The pretty stone cottage is one of four at Sproxton Hall Cottages in Sproxton, just two miles from Helmsley. There is space for four guests to sleep in two bedrooms, making it perfect for couples and families who want a peaceful location that is close to some of the region's favourite attractions such as Helmsley Castle, Pickering, Castle Howard, York, Whitby and Scarborough.

Arriving at Bilsdale Cottage is a heart-warming experience. The pretty stone cottage, which is one of four at Sproxton Hall, is set back from a private road in a quiet hamlet, only two miles south of the friendly market town of Helmsley. Guests can wake up to beautiful views of the Howardian Hills AONB and the North York Moors National Park, knowing that their day is full of spectacular scenery and memorable experiences which could even include walking around the ancient city walls of York or strolling by the seaside at Whitby or Scarborough. With space to sleep four people in two bedrooms, Bilsdale Cottage is ideal for families and couples.

Set back from a quiet road in the peaceful village of Harome, Overdale Cottage is close to the border of the North York Moors National Park and within easy reach of Helmsley, Pickering and York. The pet-friendly cottage has recently been refurbished to offer very comfortable accommodation for couples and families. There is space for four people to stay in two bedrooms, and pets are welcome. The cottage has lovely views of the surrounding countryside and is close to fantastic walks and cycle trails. There are even two excellent pubs within walking distance - the Star Inn and the Michelin-starred Pheasant, or stay in for dinner and enjoy a glass of wine in front of the open fire.

Spacious and full of character, this welcoming holiday retreat for two sits on a small dales hill farm in the North York Moors National Park. Low Crossett Cottage offers the opportunity of peace and tranquility, lovely walks, spectacular views and a comfy self-catering base for exploring the areas many attractions.

Old Bald Peg is a cottage with a pedigree as impressive as its Thoroughbred namesake. The Victorian terraced former estate cottage has been refurbished to provide a charming holiday home sleeping four guests in two bedrooms, with two well-behaved dogs welcome by prior arrangement. Situated in the quiet village of Wass, in the North York Moors National Park, within an easy stroll of two great gastropubs and the ancient ruins of Byland Abbey and close to the market towns of Helmsley, Thirsk and the historic city of York. Other local attractions include Rievaulx Abbey, Castle Howard, Sutton Bank and the Kilburn White Horse. Explore the Cleveland Way, the North Yorkshire Heritage Coast and the wild beauty of the moors.

Welcome to The Helmsley Retreat Nestled in the picturesque market town of Helmsley, The Helmsley Retreat is the perfect base for exploring North Yorkshire. This charming cottage offers modern comforts, including a private hot tub and sauna, ensuring a relaxing and memorable stay. Just a short walk from the vibrant market square with its independent shops, pubs, and cafes, the cottage combines convenience with tranquility. Ideal for couples or small families, The Helmsley Retreat provides the perfect blend of comfort, charm, and adventure.

A cosy welcoming holiday cottage with immense character, ideally placed on the edge of the North York Moors in the popular market town of Helmsley with its castle and superb walks, shops, pubs and restaurants on the doorstep. Offering a high standard of dog-friendly self-catering accommodation all year round.

"Mole End" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Lying in a sheltered corner of Upper Ryedale, on the southern edge of the North York Moors National Park, Helmsley is a prestigious market town with a spacious market square surrounded by houses, hotels and shops. The area is important...

"Sheep Cote Shepherds Hut" is a 1 bed holiday Lodge sleeping up to 2 guests in Middlesbrough. Stokesley is an attractive, elegant, historic market town which was mentioned in the Domesday Book of 1086, with many interesting Georgian and Victorian buildings. The River Leven flows through the town and is crossed by the ancient Pack Horse...

"Peep o' Day" is a 1 bed holiday Lodge sleeping up to 2 guests in York. North York Moors National Park borders Kirkbymoorside, a beautiful old market town located between Helmsley and Pickering. Located in the heart of the countryside, it exudes a distinct sense of place that can only be found in a site like this...

"Rising Sun" is a 1 bed holiday Lodge sleeping up to 2 guests in York. With Helmsley and Pickering just across the North York Moors National Park, Kirkbymoorside is a lovely historic market town. It's a wonderful spot, bursting with quintessential Yorkshire charm, and the hub of all the surrounding farms and...

"Bed in Kirkbymoorside (91049)" is a 2 bed holiday Cottage sleeping up to 3 guests in York. Steeped in history, this elegant cottage boasts a secluded patio garden and is situated in a prime location for exploring the Yorkshire Moors. This romantic bolthole is perfect for outdoorsy couples or young families holidaying with a four...

"Bed in Chop Gate (92939)" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. A cosy barn conversion set on a working farm just 3.5 miles from Chop Gate, one of the many charming villages found across the North York Moors National Park. Blessed with a spacious open plan lounge/kitchen/diner, a south facing garden and...

"Bed in Kirkbymoorside (82843)" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Escape to this beautiful stone built barn conversion, tailor made for a romantic rendezvous in the spectacular Yorkshire countryside. With rustic charm by the bucket load, a private outdoor seating area, a shared games room and even a tennis...

"Bed in Osmotherley (91336)" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Located in the idyllic village of Osmotherley, this charming cottage exudes warmth and comfort, offering a quiet retreat amidst picturesque surroundings for a couple or solo traveller. Inside, you'll find a light and airy lounge for cosy...

"The Old Forge" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Stillington is a very pretty, small rural village lying half way between York and Helmsley. The village has a Post Office/shop, several high quality pubs, an Indian restaurant, a fish and chip shop and an antiques showroom. A network of...

"Chapel Cottage" is a 2 bed holiday Cottage sleeping up to 3 guests in York. The small, pretty village of Stillington is situated between York and Helmsley and has a Post Office/shop, pubs, Indian restaurant, fish and chip shop and antiques showroom. From the village, footpaths and bridleways lead to the surrounding...

"Bed in Helmsley (TGCHF)" is a 2 bed holiday Cottage sleeping up to 4 guests in Middlesbrough. Set in a stunning location on the magnificent North York Moors, this fantastic barn conversion provides spacious, fresh and airy accommodation for couples and smaller families discovering an idyllic part of Yorkshire. Beautifully updated and...

"Bed in Hovingham (G0164)" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Escape to North Yorkshire and experience bucolic scenery, a slower pace of life and endless hiking opportunities from this Hovingham holiday home. The property is perched on the edge of the North York Moors, within reach of the vibrant...

"Foxglove Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Beadlam is a lovely village situated in the Ryedale district of North Yorkshire, resting on the edge of the North York Moors National Park, home to a farm shop and tea room, a local pub and a fish and chip shop. Helmsley market town is nearby...

"Kemps Yard Retreat" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Thirsk, gateway to North York Moors National Park to the east and Yorkshire Dales National Park to the west, has a quaint market place, fine Georgian buildings, a Norman church, and great pubs, shops, restaurants, a cinema, and a leisure...

"Bed in Thirsk (91245)" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Discover the charm of this single storey, detached cottage set on the edge of a premier fishing complex in the tranquil rural village of Sessay. With a wonderfully sociable kitchen diner and a crackling wood burner in the cosy lounge, enjoy a...

"Bed in Gillamoor (G0029)" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Set on the edge of the North York Moors National Park, this elegant hideaway is an excellent base for a pet owning couple seeking a quiet break in nature, with trips to nearby English countryside towns and an opportunity for a day by the coast....

"Bed in Gillamoor (G0066)" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Indulge in a romantic getaway with your special someone at this charming hideaway sitting in a complex of properties on the fringes of the village of Gillamoor. Sleeping two people and two woofers, it's a luxurious accommodation option for...

"2 Primrose Villas" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Kirkbymoorside is a small market town and civil parish resting in the Ryedale district of North Yorkshire. Hosting a selection of pubs, restaurants, shops and supermarkets for all of your amenities. Discover plenty of walking, hiking, cycling...

"The Granary" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Appleton-le-Moors is a delightful linear village in the heart of the North York Moors National Park. With wide green verges, where the sheep graze freely, it provides a peaceful haven in beautiful countryside. Surrounded by miles of moors and...

"West Mill Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. West Mill Cottage, a barn conversion on one level that has retained the original charming features and has lovely views, is next to the owners' house near Stittenham in the Howardian Hills. Furnished well and surrounded by farmland near Castle...

"Little Byre Cottage" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. The town of Thirsk is the gateway to the Yorkshire Dales National Park to the west and the North York Moors National Park to the east. The town offers a quaint market place, Georgian buildings, a Norman church, shops, pubs, restaurants, a...

"Bed in Easingwold (84001)" is a 2 bed holiday Cottage sleeping up to 4 guests in York. This chic, single level cottage set in the picturesque village of Crayke is dog friendly and ideal for couples or families looking for a relaxing holiday. The lovely terrace overlooks the grounds and surrounding fields. There are plenty of...

"Small Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Fadmoor, 2.5 miles from Kirkbymoorside, is a charming village with old stone cottages in the North York Moors National Park. Kirkbymoorside's many tea rooms, pubs, and restaurants will keep visitors entertained. The National Park's great...

"Cartwheel Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Yearsley is a delightful small village resting in North Yorkshire, in the heart of the Howardian Hills aonb. Yearlsey is near to the village of Ampleforth where you can find the nearest amenities including a village shop and a pub, with more...