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.

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.

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.

"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...

"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....

"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...

"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...

"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...

"Providence Court" is a 1 bed holiday Cottage sleeping up to 2 guests in York. This small, historic market town lies within the Vale of York between the City and the Hambleton Hills, on the edge of the North York Moors National Park. Picturesque and peaceful, it is a perfect introduction to Herriot Country. The town's...

"The Hayloft" is a 2 bed holiday Cottage sleeping up to 3 guests in York. The village of Husthwaite is a perfect introduction to "Herriot Country", with an old Norman church, many fine old houses and an active village hall hosting many events throughout the year. The nearby White Horse of Kilburn is a prominent local...

"2 Bed Lodge in Pickering" is a 2 bed holiday Lodge sleeping up to 4 guests in North Yorkshire. Additional information and rulesNo dogs allowed - 2 bedrooms – 1 king-size, 1 twin - 1 family bathroom with shower over bath and WC - Electric oven, induction hob, fridge/freezer, wine cooler, dishwasher and...

"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,...

"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...

"Tollerton 4" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Holiday home with one double with en suite, and one twin. Full size family bathroom. Kitchen with full size fridge/freezer, microwave and full size cooker. Double glazed and central heating. Verandah. No pets. Images are representative and may...

"Tollerton Gold Caravan" is a 2 bed holiday Caravan sleeping up to 4 guests in York. 12ft-wide caravan with one double with en suite shower, and one twin room. Central lounge area. Family bathroom. Kitchen with full size fridge/freezer, microwave and full size cooker. Double glazed and central heating. No pets. Images are...

"Beadale Cottage, Ampleforth, North Yorkshire" is a 3 bed holiday Cottage sleeping up to 5 guests in North Yorkshire. Located in the west end of the unspoilt and popular village of Ampleforth, Beadale Cottage is a stunning three bedroom hideaway with smart interiors, extensive mature gardens and private parking. Perched on an incline, this property boasts a...

"4 Bed Cottage in Kirkbymoorside" is a 4 bed holiday Cottage sleeping up to 8 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 4 bedrooms - 2 doubles, 1 twin and 1 bunk bedroom - 1 bathroom, 1 en-suite bathroom and 1 separate WC - Electric oven and hob, microwave,...

"Gardener's Lodge" is a 2 bed holiday Lodge sleeping up to 4 guests in York. Huby lies in North Yorkshire, just under twenty miles from the historic city of York, this small village is home to a selection of amenities. Purchase ingredients for a home-cooked meal from the local shop, or dine out in the pub or local...

"Lime Kiln Farm, Malton, North Yorkshire" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Perfect for families, this beautiful Grade II listed farmhouse with original features is just a short drive from the thriving town of Malton, Yorkshire's food capital. It's also just a short drive from the famous Castle Howard Estate/ Lime Kiln...

"Rye 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....

"Overcarr Cottage" is a 3 bed holiday Cottage sleeping up to 6 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...

"Helmsley Cottage" is a 3 bed holiday Cottage sleeping up to 6 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...

"2 Bed Cottage in York" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 2 bedrooms – 1 king-size and 1 twin 2'6 single beds (can be made up as a king-size on request) - 1 shower room with WC -...

"2 Bed Cottage in Ampleforth" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Additional information and rulesNo dogs allowed - 2 bedrooms – 1 king-size, 1 double - 1 shower room with shower and WC - Electric oven and hob, fridge/freezer, slim dishwasher, microwave, Dulce Gusto coffee...

"4 Bed Cottage in York" is a 4 bed holiday Cottage sleeping up to 8 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 4 bedrooms - 3 super-king-size, 1 twin room - 3 bathrooms - 1 en-suite shower with WC, 1 en-suite bathroom with bath, shower and WC and 1...

"Hinds House" is a 3 bed holiday Cottage sleeping up to 6 guests in York. Step into history with a stay at Hinds House, a charming listed cottage set within one of the turrets of Castle Howard’s historic fortified walls, part of the estate’s original deer park. Just a leisurely 20-minute stroll (or short...

"Mistal Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in York. The small market town of Easingwold is set within the Vale of York, on the edge of the North York Moors National Park. The town centre boasts a large market square surrounded by splendid Georgian buildings, plus there are also pretty village...