Self Catering Holiday Cottages in Helmsley

Bilsdale Cottage is a hidden gem on the edge of the North York Moors National Park and within the Howardian Hills National Landscape. This historic stone cottage, which is one of four at Sproxton Hall Cottages, is set back from a private road on the edge of a quiet hamlet, only two miles south of the tourist friendly market town of Helmsley.  With space to sleep four people in two bedrooms, Bilsdale Cottage is ideal for families and couples. The cottage welcomes 3 dogs and has its own enclosed garden. Dogs can also enjoy the onsite dog exercise paddock and the bridleway at the end of the drive. Guests can wake up to beautiful far reaching views, knowing that their day is full of spectacular scenery and memorable experiences which could include walking around the ancient city walls of York, savouring the splendour or Castle Howard, strolling by the seaside at Whitby or feeling nostalgic in Herriot Country. Helmsley and its surrounding villages has a growing reputation for high quality restaurants, as well as plenty of traditional dog friendly country pubs.

Enjoy the beauty of the North York Moors National Park and the Howardian Hills National Landscape from the comfort of Ryedale Cottage. The pretty stone cottage is one of four at Sproxton Hall Cottages, 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 steam railway, Castle Howard, York, Whitby and Herriot Country. Ryedale Cottage is single-storey and has floor to ceiling windows in the living area, old beams and historic stonework. A log burner makes for a cosy stay.

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.

"Lockton Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Pickering is a market town offering traditional shops, pubs and restaurants and serves as the official gateway to the North York Moors National Park. The Beck Isle Museum is well worth visit, plus take a ride on the steam railway. There are...

"Chloe's Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in North Yorkshire. Middleton is a small village in Ryedale, situated between both the market towns of Kirkbymoorside and Pickering. The village is located close south of the North York Moors National Park, which means there are several walking and cycling routes...

"Ickle Pickle Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Thirsk, a bustling market town in the Yorkshire Dales and the gateway to the North York Moors National Parks on the east and the Yorkshire Dales on the west, is home to beautiful Georgian buildings, a Norman church, and a variety of great pubs,...

"Rose Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in York. Sheriff Hutton is a small village resting between the hills of York and Malton. The village is steeped with history, with ruins of a 14th century castle, housing Richard III in 1483, and a medieval church with Norman tower dating from 1100....

"The Old Cartway" is a 4 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Pickeringh has a range of shops, cafes, pubs and restaurants, it serves as the official gateway to the North York Moors National Park, home of the Heartbeat countryside. You can ride on the North Yorkshire Moors Steam Railway, where some of the...

"The Old Post Office" is a 5 bed holiday Cottage sleeping up to 10 guests in York. The unspoiled village of Ampleforth, which is home to a few old homes, two pubs, a tearoom, and the neighbourhood store, is situated on the edge of the North York Moors National Park. There are several excellent restaurants nearby, and the...

"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...

"1 The Old Methodist Chapel" is a 4 bed holiday Cottage sleeping up to 8 guests in North Yorkshire. Perfectly positioned for touring both the Moors and the Coast, the picturesque village of Rosedale Abbey is situated in the heart of the North York Moors National Park. Located in Rosedale, a beautiful valley of sweeping hillsides and...

"Bay Tree Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. This historic market town, with its full range of amenities and traditional shops, cafes, pubs and restaurants, serves as the official gateway to the beautiful North York Moors National Park, home of the Heartbeat countryside. Enjoy a ride on...

"Ford End Cottage" is a 3 bed holiday Cottage sleeping up to 6 guests in York. Ampleforth is a small village situated in the North York Moors National Park, home to a local shop, two pubs, takeaway and ancient houses, whilst the market town of Helmsley is just a short journey away surrounded by a host of restaurants and...

"Cobbler's Cottage" is a 3 bed holiday Cottage sleeping up to 5 guests in North Yorkshire. The historic market town of Pickering has many amenities including traditional shops, tea rooms, pubs and restaurants. The town is often referred to as the gateway to the breathtaking North York Moors National Park. Attractions that are well...

"The Green, Castle Howard, Coneysthorpe" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. This delightful 18th Century stone cottage brings you a beguiling mix of contemporary comforts with timeless elegance, thanks to carefully-chosen modern fixtures and fittings that blend perfectly with period furniture taken from Castle Howard...

"5 Bed Cottage in Pickering" is a 5 bed holiday Cottage sleeping up to 11 guests in North Yorkshire. Additional information and rulesNo dogs allowed - 5 bedrooms - Super king, 2 x King (one with additional single bed), 2 x Doubles (one with additional single bed) - 1 bathroom and 1 shower room with separate WC - Electric oven...

"Fairview (2), Ampleforth, York, North Yorkshire" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Set within the picturesque village of Ampleforth, Fairview is a charming stone cottage offering comfortable accommodation for two people and boasting far reaching rooftop views from the delightful rear garden. Located within close reach of...

"Stable Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Set amidst the beautiful countryside of the Howardian Hills, the pretty North Yorkshire village of Hovingham is located in an Area of Outstanding Natural Beauty. The village itself is incredibly picturesque, with a beck running down the high...

"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...

"The Old Post Office" is a 5 bed holiday Cottage sleeping up to 9 guests in North Yorkshire. Situated in the heart of the North York Moors National Park and handily placed for touring both the Moors and the Coast, the picturesque village of Rosedale Abbey is set within Rosedale, a beautiful valley of sweeping hillsides and...

"Fairview, Ampleforth, York, North Yorkshire" is a 2 bed holiday Cottage sleeping up to 3 guests in North Yorkshire. Tastefully modernised to a high standard this cosy hideaway includes features such as pine panelled doors, underfloor heating throughout the ground floor, beamed ceilings and exposed stone walls. The thoughtfully decorated sitting room...

"Erica's 'eaven" is a 1 bed holiday Cottage sleeping up to 3 guests in North Yorkshire. The attractive old market town of Kirkbymoorside lies on the edge of the North York Moors National Park, in between the towns of Helmsley and Pickering. It is a charming place, full of Yorkshire character, and is the centre for the local farms...

"Lark Rise, Thirsk" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Lark Rise dates back over two hundred years and has been lovingly renovated to provide comfortable holiday accommodation. Enter via the porch into a wonderful dining area leading guests through to the well-equipped kitchen on the right or step...

"4 Bed Cottage in Borrowby" is a 4 bed holiday Cottage sleeping up to 7 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 4 bedrooms – 1 super-king-size zip-and-link (converts to twin on request), 1 king-size, 1 twin, 1 single - 3 bathrooms – 1 family...

"1 Castle Terrace" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Thame is a charming market town in Oxfordshire resting between Oxford and Aylesbury. This wonderful town is named after the River Thames which runs through it and is known for the Thame Abbey which was founded in 1137 and destroyed during the...

"Mill View" is a 2 bed holiday Cottage sleeping up to 4 guests in York. The attractive old market town of Kirkbymoorside lies on the edge of the North York Moors National Park, in between the towns of Helmsley and Pickering. It is a charming place, full of Yorkshire character, and is the centre for the local farms...

"Spruce Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in York. Boutique, cosy and one of a kind Spruce is a unique luxury lodge designed for those who love style and comfort. Think Italian sofas, a coffee machine, a Ninja air fryer, and an egg BBQ for perfect outdoor dining. The bedrooms are dreamy —...