Find My Favourite Holiday Cottages in Helmsley

Helmsley is a medieval market town in Yorkshire’s unspoiled Ryedale district. It lies on the southern boundary of the North York Moors National Park, where the dale leaves the moorland and meets the flatter scenery of the Vale of Pickering. From holiday cottages in Helmsley, a short stroll will bring you to the town centre, much of which is a conservation area, thanks to its unique historical landmarks. A maze of pretty streets surrounds the marketplace, lined with a selection of independent shops, including Room for Antiques and Bondgate Antiques. Thomas the Bakery has a reputation for delicious treats, and Helmsley Brewing Co. is the place to go for craft beers. You’ll also find some of the region’s best eateries, where you can enjoy delicious food prepared with fresh ingredients from the surrounding fields. From beautiful gardens to live entertainment, there’s no shortage of things to do on self-catering holidays in Helmsley. Check out Helmsley Arts Centre for live music, comedy, films and art exhibitions.

Exterior of a stone cottage with enclosed porch and sun lounge overlooking a lawn.
Sleeps
11
Bedrooms
4

Castle View is a tastefully furnished, large, family-friendly village holiday cottage in Helmsley in the heart of the North York Moors National Park. It is also within an easy drive of the North Yorkshire coast. This dog-friendly holiday let sleeps 11 in 4 bedrooms.

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A stone built holiday cottage in Hovingham overlooks a steam running past its frontage on a summer's day.
Sleeps
6
Bedrooms
3

Harwood Cottage is a truly elegant stone cottage set beside a small stream in Hovingham, Yorkshire, sleeping 6. A lawned garden hosts the conservatory, while the interior features a log fire in the sitting room and many original details lovingly restored, combined with contemporary comforts.

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Stone-built, barn conversion exterior with a raised, secure BBQ terrace.
Sleeps
10
Bedrooms
4

The Old Cart House is a large luxury barn conversion in the North York Moors, situated on a hill farm in Farndale near Helmsley; a genuinely stunning renovation from top to bottom, this large holiday home in North Yorkshire boasts top-of-the-range decor throughout and contemporary finishes, perfect for group and large family holidays. Pets welcome.

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A stone-built, 2-storey holiday cottage in Helmsley overlooking a large lawn.
Sleeps
4
Bedrooms
2

Based on a working livestock farm, Wethercote Cottage is an authentic farmhouse adjoined to the owner’s home in the heart of the North York Moors near Helmsley. This remote 2-bedroom rural retreat is ideal for walking or cycling holidays. Pets welcome.

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L=shaped rural holiday bungalow surrounded by a large hedge and parking spaces.
Sleeps
2
Bedrooms
1

Applewood is a pretty one-bedroom cottage situated in the village of Harome near Helmsley within walking distance of the Michelin-starred Star Inn and nestled between the North Yorkshire Moors National Park and the Howardian Hills, a designated Area of Outstanding Natural Beauty.

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Visible from most Helmsley holiday homes, Helmsley Castle looms over the town. Reserve an hour or two to discover how the castle evolved over the centuries, from a medieval fortress to an extravagant Tudor mansion. Nearby, the ancestral home of the Earls of Feversham, Duncombe Park, is a magnificent stately home surrounded by 30 acres of stunning gardens. The ruins of Byland and Rievaulx nestle in neighbouring valleys, surrounded by tranquil countryside full of birdsong.

A stone’s throw to the north of Helmsley, the North York Moors National Park is a paradise for walking, horse-riding and wildlife-watching. This expanse of high, heather moorland and lush, green valleys is crisscrossed by scenic footpaths that follow ancient roads’ routes. If you fancy a day on the beach, the classic resort of Scarborough is less than an hour’s drive eastward on the A170. Twenty-four miles north of Helmsley, York is a fascinating city with some of England’s most impressive architecture.