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 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.

View holiday cottages in Pickering
Pickering cottages

Popular cottages in Pickering

Exterior | Chestnut  Cottage, Ebberston, nr. Scarborough
Customers' Choice

Ebberston, near Scarborough, Yorkshire

Chestnut Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

2 nights

From

£249
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Blossom

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

2 nights

From

£535
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering
Customers' Choice

Lockton, near Pickering, Yorkshire

Horcum View

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

4 nights

From

£285
View
Open plan living space | Oak Lodge - Southolme Lodges, Pickering

Pickering, Yorkshire

Southolme Lodges - Oak Lodge

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

4.3

out of 5

2 nights

From

£269
View
Garden | Rawcliffe House Farm - Giltspur, Stape, nr. Pickering

Stape, near Pickering, Yorkshire

Giltspur

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 7
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£1,110
View
Living room | Kays Cottage, Middleton, near Pickering

Middleton, near Pickering, Yorkshire

Kays Cottage

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.5

out of 5

4 nights

From

£279
View
Balcony | Castle Cottage, Pickering

Pickering, Yorkshire

Castle Cottage

Pets stay free
Wifi
Garden / Patio
Woodburning Stove
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.3

out of 5

4 nights

From

£309
View
Exquisite holiday cottage | Cherry Laurel - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Laurel

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£505
View
Exterior | Hill View Cottage, Sinnington near Pickering
Customers' Choice

Sinnington near Pickering, Yorkshire

Hill View Cottage

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

2 nights

From

£369
View
Exterior | Fox Cub Cottage - Fox and Rabbit Holiday Cottages, Lockton, near Pickering
Customers' Choice

Lockton, near Pickering, Yorkshire

Fox Cub Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

2 nights

From

£335
View

Dog friendly cottages in Pickering

Exterior | Chestnut  Cottage, Ebberston, nr. Scarborough
Customers' Choice

Ebberston, near Scarborough, Yorkshire

Chestnut Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.9

out of 5

2 nights

From

£249
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Blossom

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

2 nights

From

£535
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering
Customers' Choice

Lockton, near Pickering, Yorkshire

Horcum View

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

4 nights

From

£285
View
Living room | Kays Cottage, Middleton, near Pickering

Middleton, near Pickering, Yorkshire

Kays Cottage

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

4.5

out of 5

4 nights

From

£279
View
Balcony | Castle Cottage, Pickering

Pickering, Yorkshire

Castle Cottage

Pets stay free
Wifi
Garden / Patio
Woodburning Stove
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.3

out of 5

4 nights

From

£309
View
Exquisite holiday cottage | Cherry Laurel - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Laurel

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£505
View
Exterior | Hill View Cottage, Sinnington near Pickering
Customers' Choice

Sinnington near Pickering, Yorkshire

Hill View Cottage

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

2 nights

From

£369
View
Exterior | Fox Cub Cottage - Fox and Rabbit Holiday Cottages, Lockton, near Pickering
Customers' Choice

Lockton, near Pickering, Yorkshire

Fox Cub Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

2 nights

From

£335
View
Living room | The Swiss Cottage, Pickering

Pickering, Yorkshire

The Swiss Cottage

Pets stay free
Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

6 nights

From

£505
View

Luxury cottages in Pickering

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

Thornton le Dale near Pickering, Yorkshire

Cherry Blossom

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

2 nights

From

£535
View
Exquisite holiday cottage | Cherry Laurel - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Laurel

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£505
View
Exterior | Hill View Cottage, Sinnington near Pickering
Customers' Choice

Sinnington near Pickering, Yorkshire

Hill View Cottage

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

2 nights

From

£369
View
Garden | Rinstone Lodge, Thornton le Dale, near Pickering
Customers' Choice

Thornton le Dale, near Pickering, Yorkshire

Rinstone Lodge

Hot Tub
Luxury
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

4 nights

From

£685
View
Living room | Cherry Garth Cottages : Cherry Garth - Cherry Garth Cottages, Thornton le Dale near Pickering
Customers' Choice

Thornton le Dale near Pickering, Yorkshire

Cherry Garth Cottages : Cherry Garth

Pets stay free
Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

4 nights

From

£525
View

Newton-on-Rawcliffe, near Pickering, Yorkshire

Holly House - Holly House Barn 1

Luxury
Wifi
Car parking on site
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

2 nights

From

£299
View
Exterior | Forge Gardens, Thornton Le Dale, near Pickering
Customers' Choice

Thornton Le Dale, near Pickering, Yorkshire

Forge Gardens

Pets stay free
Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

4 nights

From

£485
View
Living room | Box Tree Cottage, Pickering
Customers' Choice

Pickering, Yorkshire

Box Tree Cottage

Pets stay free
Luxury
Wifi
Car parking on site
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

6 nights

From

£655
View
Delightful open-plan living space | West Wood Hideaway, Wrelton, near Pickering
Customers' Choice

Wrelton, near Pickering , Yorkshire

West Wood Hideaway

Luxury
Wifi
Car parking on site
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

2 nights

From

£325
View
Living room | Bo Peep Cottage, Thornton-Le-Dale

Thornton-Le-Dale, Yorkshire

Bo Peep Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 5
  • 3 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

3

out of 5

5 nights

From

£479
View
Kitchen | 1 Chapel Terrace, Pickering

Pickering, Yorkshire

1 Chapel Terrace

Luxury
Wifi
Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.9

out of 5

4 nights

From

£289
View
Hot tub | The Workshop - Ryehills Farm, Pickering

Pickering, Yorkshire

Ryehills Farm - The Workshop

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£745
View

Romantic cottages in Pickering

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

Thornton le Dale near Pickering, Yorkshire

Cherry Blossom

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.5

out of 5

2 nights

From

£535
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering
Customers' Choice

Lockton, near Pickering, Yorkshire

Horcum View

Pets stay free
Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

4 nights

From

£285
View
Balcony | Castle Cottage, Pickering

Pickering, Yorkshire

Castle Cottage

Pets stay free
Wifi
Garden / Patio
Woodburning Stove
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

4.3

out of 5

4 nights

From

£309
View
Exquisite holiday cottage | Cherry Laurel - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Laurel

Pets stay free
Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

2 nights

From

£505
View
Exterior | Hill View Cottage, Sinnington near Pickering
Customers' Choice

Sinnington near Pickering, Yorkshire

Hill View Cottage

Pets stay free
Hot Tub
Luxury
Wifi
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

4.7

out of 5

2 nights

From

£369
View
Living room | The Swiss Cottage, Pickering

Pickering, Yorkshire

The Swiss Cottage

Pets stay free
Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 6
  • 3 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

6 nights

From

£505
View
Garden | Rinstone Lodge, Thornton le Dale, near Pickering
Customers' Choice

Thornton le Dale, near Pickering, Yorkshire

Rinstone Lodge

Hot Tub
Luxury
Wifi
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

5

out of 5

4 nights

From

£685
View
Living room | Cherry Garth Cottages : Cherry Garth - Cherry Garth Cottages, Thornton le Dale near Pickering
Customers' Choice

Thornton le Dale near Pickering, Yorkshire

Cherry Garth Cottages : Cherry Garth

Pets stay free
Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

4 nights

From

£525
View
Exterior | Mulberry Hayloft, Little Barugh, near Pickering

Little Barugh, near Pickering, Yorkshire

Mulberry Hayloft

Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 6
  • 3 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

6 nights

From

£495
View

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

  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

Bonus: 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.