Pickering Cottages

Self-catering holiday cottages in Pickering

Our self-catering holiday cottages in Pickering are well placed for exploring the surrounding North Yorth Moors National Park and nearby Yorkshire Coast. Whether you're looking for a romantic retreat in the nearby countryside, a family-friendly holiday home close to the centre of the market town or a dog-friendly cottage with walks from the front door, our hand-picked collection of almost 100 Pickering properties has something to suit everyone

Many of our Pickering cottages are full of character, with features such as exposed beams, wood burners and enclosed gardens. Alongside rural barn conversions in peaceful countryside spots, you’ll find properties in nearby pretty villages like Thornton-le-Dale and traditional stone cottages in the centre of town within easy reach of the town's independent shops, pubs and cafés.

With much to see and do in and around the popular North Yorkshire town, Pickering is a great choice for fun-filled days out and exploring the history and heritage of the area before returning to a comfortable cottage at the end of the day.

Discover Pickering and the surrounding area

Not only is the attractive market town of Pickering well placed for exploring the North York Moors and enjoying days out at the Yorkshire Coast, but it’s full of independent shops, cafes and art galleries, with a regular market each Monday in the town’s historic marketplace.

On an elevated spot on the edge of town lies Pickering Castle, an English Heritage site with ancient ruins, fields of wildflowers and spectacular views across the Vale of Pickering.

One of the town's best-known attractions is the North Yorkshire Moors Railway, where heritage steam trains travel through the moors, passing through stations at Levisham, Goathland and Grosmont on their way to Whitby.  Spend the day enjoying some fresh sea air and tasty fish and chips before heading back to Pickering. Closer to home, Beck Isle Museum offers an insight into local life through the centuries, while nearby Cedarbarn Farm Shop has a miniature railway and play area for little ones along with various pick your own experiences throughout the year.

For a dog-friendly day out that’s fun for the rest of the family too, head to Dalby Forest where you’ll find walking trails, cycle routes and a variety of activities including Go Ape tree top courses and orienteering.

Pickering is also perfectly placed for exploring the wider region. Head to the handsome market town of Helmsley and enjoy a picnic alongside the River Rye or spend a day discovering York's historic streets and attractions. Nearby historic houses worth visiting include Castle Howard and Nunnington Hall and your just a short drive away from one of Yorkshire’s best theme parks, Flamingo Land, where you can have a fun day out with the kids.

Find your perfect Pickering cottage

If this has put you in the mood for a getaway to Pickering, whether for a last-minute short break or a longer summer holiday, browse our hand-picked collection of self-catering cottages in and around the market town. Use the filters on the left-hand side of the page to find luxury cottages or properties with features such as games rooms and hot tubs.