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.

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.

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.

"Brewers Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Middleton is a small, rural village settled between the market towns of Kirkbymoorside and Pickering in Ryedale. The village rests just south of the North York Moors National Park, meaning a wealth of walks and cycling routes are just a stone's...

"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...

"Ascot Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Strensall offers good amenities including pubs, shops, a hairdressers, a bakery and a fish and chip shop, and there is also a village park and a superb golf course. The surrounding countryside offers good walking and cycling, with routes...

"The Burrows" is a 3 bed holiday Cottage sleeping up to 5 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...

"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...

"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...

"Wethercote Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Situated on the southern edge of the North York Moors National Park and set in a sheltered corner of Upper Ryedale, Helmsley is a vibrant market town with a spacious square. Surrounded by houses, hotels and shops, the town centre is a lively...

"Low Grounds Cottage" is a 2 bed holiday Cottage sleeping up to 4 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...

"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...

"Maple Tree Lodge" is a 1 bed holiday Lodge sleeping up to 2 guests in York. A satellite village to the north of York, Strensall offers excellent transport links into the historic city centre. This friendly village has good amenities including pubs, shops, a hairdressers, a bakery and a fish & chip shop. There is...

"Meadow Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in York. The market town of Kirkbymoorside is on the edge of the North York Moors, in between Helmsley and Pickering. It has variety of shops, tea rooms, pubs and restaurants along with antique shops and a weekly market. The walking and scenery 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...

"Robin Cottage - Pickering" is a 1 bed holiday Cottage sleeping up to 3 guests in North Yorkshire. An exquisite cottage in the heart of beautiful North Yorkshire, this delightful hideaway makes an idyllic romantic retreat. Sleeping three guests, the one-bedroom bolthole is one of three similar high-quality holiday homes set on a working...

"Owl's Nest" is a 1 bed holiday Cottage sleeping up to 2 guests in York. The small, peaceful village of Brandsby lies in the Vale of York, surrounded by the beautiful, rolling countryside of the Howardian Hills, an Area of Outstanding Natural Beauty. Close by is Crayke with an award winning gastro pub, whilst nearby...

"Cherry Tree House" is a 4 bed holiday Cottage sleeping up to 8 guests in North Yorkshire. Cherry Tree House is a beautiful luxury property near the centre of Helmsley. With stunning contemporary kitchen diner, quirky garden room, four double bedrooms and a garden with patio and outside seating, it is an ideal place for families and...

"Spring Cottage" is a 2 bed holiday Cottage sleeping up to 4 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 Woodpecker View - Pickering" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Tucked away in the heart of the countryside, this beautifully refurbished two-bedroom cottage offers the perfect escape for couples, families or friends looking for peace, comfort and a touch of rural charm. Whether you’re seeking countryside...

"3 Valley View Lodges" is a 2 bed holiday Lodge sleeping up to 4 guests in York. Helmsley is a town, on the edge of the North York Moors National Park, with a market square, shops, an arts centre showing films and plays, and a seasonal outdoor swimming pool. Helmsley has a 12th century castle, with English Heritage’s...

"Griff Lodge" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Harome is a little village resting in the Ryedale district of North Yorkshire, around two miles from the south-east market town of Helmsley. The cobbled streets of the village are lined with old stone cottage and surround the picturesque pond...

"2 Bed Cottage in Brandsby" is a 2 bed holiday Cottage sleeping up to 4 guests in York. Additional information and rules - 2 bedrooms – 1 super-king-size and 1 twin - 2 bathrooms – 1 wet room with WC, 1 en-suite shower room with WC - Electric oven and hob, fridge/freezer, separate fridge, dishwasher, washing machine and...

"Brook Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in York. The tranquil little village of Brandsby in the Vale of York is situated in an Area of Outstanding Natural Beauty surrounded by the Howardian Hills. Crayke with its award winning pub, Stillington with two pubs and a local shop, and the bustling...

"Jenny's Cottage" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Osmotherley, a North Yorkshire conservation village nestled between the Cleveland Hills to the east and the Yorkshire Dales to the west, has grass and tree-lined streets and sits on the western fringe of the North York Moors National Park. The...

"Ryedale Country Lodges - Willow Lodge" is a 3 bed holiday Lodge sleeping up to 5 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...

"Badger" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. With the gateway to the North York Moors National Park to the east and Yorkshire Dales National Park to the west, the bustling town of Thirsk boasts a quaint market place, splendid Georgian buildings, and a Norman church. Here there are a...