Pickering Cottages

This charming town, known as the 'Gateway to the Moors' is nestled in between four major Yorkshire towns of Scarborough, Whitby, Helmsley and Malton. Ideally placed for a short break or a longer stay exploring this picturesque area, either by foot or bike. Packed with farm shops to help you pick up some locally sourced produce and head back to your home away from home to enjoy some quality time with your loved ones. If you fancy someone else doing the cooking, there are plenty of cosy tearooms and pubs where you can sit back and relax. On the edge of the North York Moors, this enchanting region comprises 1400 miles of heather moorland, pine forests, rolling hills and a stunning coastline. Along the trails and routes, look out for historic abbeys, castles and priories, traditional villages and hamlets. Breathe out, kick back and enjoy creating memories in one of our Pickering cottages.

Wildlife surrounding Pickering

Popular Cottages in Pickering

Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£559
View
Reserve today for only £25
Open plan living space | West Wood Cottage, Wrelton, near Pickering

Wrelton, near Pickering, North Yorkshire

West Wood Cottage

Luxury
Wifi
Car parking on site
  • 3 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

5

out of 5

7 nights

From

£327
View
Delightful open-plan living space | West Wood Hideaway, Wrelton, near Pickering

Wrelton, near Pickering, North Yorkshire

West Wood Hideaway

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£327
View
Reserve today for only £25
Well presented living room with cosy wood burner | Hillcrest, Pickering

Pickering, North Yorkshire

Hillcrest

Enclosed Garden / Patio
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£317
View
Reserve today for only £25
Exterior | Pan cottage, Middleton

Middleton, North Yorkshire

Pan cottage

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.8

out of 5

7 nights

From

£287
View
Southolme Lodges - Sycamore Lodge, Pickering

Pickering, North Yorkshire

Southolme Lodges - Sycamore Lodge

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.7

out of 5

7 nights

From

£263
View
Reserve today for only £25
Exterior | Craven Bungalow, Allerston, near Pickering

Allerston, near Pickering, North Yorkshire

Craven Bungalow

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£589
View
Reserve today for only £25
Living room | The Ridings, Thornton le Dale

Thornton le Dale, North Yorkshire

The Ridings

Car parking on site
Enclosed Garden / Patio
Garden / Patio
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.3

out of 5

7 nights

From

£463
View
Sitting-out-area | Morgan’s Rest, Pickering

Pickering, North Yorkshire

Morgan’s Rest

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

5

out of 5

7 nights

From

£635
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, North Yorkshire

Cherry Blossom

Luxury
Wifi
Enclosed Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£523
View

Dog Friendly Cottages in Pickering

Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£559
View
Reserve today for only £25
Exterior | Pan cottage, Middleton

Middleton, North Yorkshire

Pan cottage

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.8

out of 5

7 nights

From

£287
View
Living room | The Ridings, Thornton le Dale

Thornton le Dale, North Yorkshire

The Ridings

Car parking on site
Enclosed Garden / Patio
Garden / Patio
  • 7 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.3

out of 5

7 nights

From

£463
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, North Yorkshire

Cherry Blossom

Luxury
Wifi
Enclosed Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£523
View
Exterior | Fox Cub Cottage - Fox and Rabbit Holiday Cottages, Lockton, near Pickering

Lockton, near Pickering, North Yorkshire

Fox Cub Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

7 nights

From

£575
View
Charming holiday home | Bank Top Cottage, Cropton, near Pickering

Cropton, near Pickering, North Yorkshire

Bank Top Cottage

Wifi
Car parking on site
Pub within 1 mile
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.7

out of 5

7 nights

From

£527
View
Exterior | Evergreen Cottage, Sinnington, nr. Pickering

Sinnington, near Pickering, North Yorkshire

Evergreen Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 2 Pets

5

out of 5

7 nights

From

£423
View
Reserve today for only £25
Exterior | Westfield Farm, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Westfield Farm

Luxury
Wifi
Car parking on site
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 1 Pet

5

out of 5

7 nights

From

£910
View
Charming cottage | Four Seasons, Pickering

Pickering, North Yorkshire

Four Seasons

Wifi
Car parking on site
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

4.7

out of 5

7 nights

From

£625
View
Reserve today for only £25

Luxury Cottages in Pickering

Garden | Rinstone Lodge, Thornton le Dale, near Pickering

Thornton le Dale, near Pickering, North Yorkshire

Rinstone Lodge

Hot Tub
Luxury
Wifi
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

7 nights

From

£828
View
Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • 5 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 2 Pets

5

out of 5

7 nights

From

£559
View
Reserve today for only £25
Open plan living space | West Wood Cottage, Wrelton, near Pickering

Wrelton, near Pickering, North Yorkshire

West Wood Cottage

Luxury
Wifi
Car parking on site
  • 3 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

5

out of 5

7 nights

From

£327
View
Delightful open-plan living space | West Wood Hideaway, Wrelton, near Pickering

Wrelton, near Pickering, North Yorkshire

West Wood Hideaway

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£327
View
Reserve today for only £25
Living room | Willowfield Cottage, Thornton-Le-Dale

Thornton-Le-Dale, North Yorkshire

Willowfield Cottage

Hot Tub
Luxury
Wifi
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

7 nights

From

£705
View
Exterior | Craven Bungalow, Allerston, near Pickering

Allerston, near Pickering, North Yorkshire

Craven Bungalow

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

4.9

out of 5

7 nights

From

£589
View
Reserve today for only £25
Sitting-out-area | Morgan’s Rest, Pickering

Pickering, North Yorkshire

Morgan’s Rest

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 0 Pets

5

out of 5

7 nights

From

£635
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, North Yorkshire

Cherry Blossom

Luxury
Wifi
Enclosed Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£523
View
Living room | 4 Smiddy Hill, Pickering

Pickering, North Yorkshire

4 Smiddy Hill

Luxury
Wifi
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 0 Pets

5

out of 5

7 nights

From

£483
View
Exterior | Westfield Farm, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Westfield Farm

Luxury
Wifi
Car parking on site
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 1 Pet

5

out of 5

7 nights

From

£910
View
Living room | Bo Peep Cottage, Thornton-Le-Dale

Thornton-Le-Dale, North Yorkshire

Bo Peep Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • 5 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 0 Pets

7 nights

From

£705
View
Exterior | Warrington House - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Warrington House

Luxury
Wifi
Enclosed Garden / Patio
  • 9 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£795
View
Reserve today for only £25

Inspiration of things to see and do in Pickering

This charming market town in North Yorkshire offers a mix of historical sites, natural beauty, and cultural attractions. Explore the nearby village of Thornton-le-Dale with its charming thatched cottages, visit the Ryedale Folk Museum, or take a short drive to the historic city of York. With the largest collection of Yorkshire cottages, we have the perfect home away from home for you.

Here are the top five things to see and do in Pickering:

North York Moors Railway

Experience a journey on the North York Moors Railway, a heritage steam railway that runs through stunning countryside, including a stop at Pickering Station.

Pickering Castle

Explore Pickering Castle, a well-preserved Norman castle with panoramic views of the town and surrounding landscapes. Learn about its history and architecture.

Beck Isle Museum

Visit the Beck Isle Museum, a fascinating local history museum showcasing Pickering's past through exhibits on rural life, industry, and everyday objects.

Pickering Parish Church

Admire the architecture of Pickering Parish Church, dedicated to St. Peter and St. Paul. Explore the church's interior, stained glass windows, and historical features.

Dalby Forest

Enjoy outdoor activities in Dalby Forest, located near Pickering. Hike, bike, or take a leisurely walk through the woodland trails and enjoy the natural beauty.

More Popular Holiday Destinations

Reeth cottages

Whitby cottages

Scarborough cottages

Helmsley cottages

Malton cottages

Wildlife surrounding Pickering

Explore

A father hugging his son

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