Self Catering Holiday Cottages in Helmsley

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.

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.

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.

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.

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.

"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...

"Peg's Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. On the southern edge of the North York Moors National Park is the prestigious market town of Helmsley. Lying in a sheltered corner of Upper Ryedale, this lovely settlement boasts a spacious market square surrounded by houses, hotels and shops...

"1 Bed Cottage in Bilsdale" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 bedroom – king-size - 1 en-suite shower room with WC, separate WC - Electric hob/oven, full sized fridge freezer, dishwasher, microwave,...

"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...

"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...

"Lime Kiln Farmhouse, Castle Howard, Coneysthorpe" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. This pretty stone built 18th century farmhouse with views of Castle Howard is situated in the attractive rural Castle Howard estate village of Coneysthorpe with easy access onto the Centenary Way. Furnished and decorated by the late Lady Susan...

"3 Bed Cottage in Pickering" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 3 bedrooms – 1 king-size, 1 double, 1 twin - 1 bathroom with a bath and shower and WC - Electric oven & induction hob,...

"Isca Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in York. The small village of Wombleton lies in Ryedale, on the edge of the North York Moors National Park. Three miles from both Helmsley and Kirkbymoorside, Wombleton still retains some farming heritage, with several working farms in the village....

"Oak Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in North Yorkshire. Nestled between York and Malton, the village of Sheriff Hutton is within the Ryedale district of Yorkshire. There is a village green and two pubs, both serving food, one dating back to the 1600s. The City of York is only 11 miles away, while...

"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...

"3 Bed Cottage in Pickering" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Additional information and rulesNo dogs allowed - 3 bedrooms – 2 doubles and 1 twin - 1 bathroom with shower over the bath and WC - Electric oven and hob, fridge/freezer, microwave, and washing machine - Travel cot and...

"1 Bed Cottage in York" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 Bedroom – king-size - 1 shower room with shower and WC - Electric oven and hob, microwave, fridge/freezer and dishwasher - please note...

"Daleside Chapel" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. A striking countryside retreat offering space, scenery and standout design, this distinctive escape is perfect for relaxed gatherings, scenic adventures and memorable stays in a wonderfully peaceful North York Moors setting.. 2 steps to...

"3 Bed Cottage in Crayke" is a 3 bed holiday Cottage sleeping up to 5 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 3 bedrooms – 1 king, 1 bunk bedroom, 1 double - 2 bathrooms – 1 bathroom with a bath and a WC, 1 en-suite shower room with a walk-in...

"The Cart House" is a 3 bed holiday Cottage sleeping up to 6 guests in York. The Cart House is a beautiful stone property, with all the character and charm you could wish for. Located in the beautiful town of Helmsley in the North York Moors National Park.. Ground Floor: Living/dining...

"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...

"Riccal Heads" is a 3 bed holiday Cottage sleeping up to 6 guests in York. Enjoy a leisurely journey on the North York Moors Steam Railway, which departs just 10 miles from the property.. 1 step to entrance. All on the Ground Floor: Open plan living space. Living...

"Clothfair" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Easily visit the attractions of the North York Moors and coast from this property, including Pickering, Whitby, Malton, Helmsley and Kirkbymoorside.. All on the Ground Floor: Open plan living...

"Cropton Lodge" is a 2 bed holiday Lodge sleeping up to 2 guests in North Yorkshire. Compact lodge finished to a high standard with one double and one with bunks. Shower. Open plan lounge/kitchen/dining area. Decking area with outdoor hot tub.. Pickering Lodges is part of our Evermore Lodge Holidays Collection, a luxurious...

"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...

"Feather Holme Farm Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Ground Floor: Living/dining room: TV, DVD Player, Woodburner, French Doors Leading To Garden Kitchen: Electric Oven, Electric Hob, Microwave, Fridge, Washing Machine Bedroom...

"Rowan Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in York. New for 2020. Superb contemporary furnished lodge with large interior living space. One king-size double bedroom with en suite shower. One twin room. House bathroom with bath and overhead shower. Outdoor hot tub situated on south facing...

"Newton Dale Lodge" is a 3 bed holiday Lodge sleeping up to 4 guests in North Yorkshire. Luxury lodge with one double with en suite shower, one twin and one twin with child size beds. Bath with overhead shower. Fridge/freezer. Spacious open-plan living area with large verandah overlooking the lake. Outdoor hot tub. No pets. Images...