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

Exterior | Mill Cottage, Pickering

Pickering, Yorkshire

Mill Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£795
View
Living room | 4 Smiddy Hill, Pickering

Pickering, Yorkshire

4 Smiddy Hill

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

5

out of 5

7 nights

From

£559
View
Living room | Hallgarth House, Pickering

Pickering, Yorkshire

Hallgarth House

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 10
  • 5 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£845
View
Reserve today for only 25%
Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.8

out of 5

7 nights

From

£493
View
Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£575
View
Exterior | Evergreen Cottage, Sinnington, nr. Pickering

Sinnington, near Pickering, Yorkshire

Evergreen Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£423
View
Reserve today for only £25
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

4.5

out of 5

7 nights

From

£287
View
Reserve today for only £25
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

5

out of 5

7 nights

From

£705
View
Reserve today for only £25
Perfect holiday hideaway | Saltersgate - Hungate Cottages, Pickering

Pickering, Yorkshire

Hungate Cottages - Saltersgate

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 7
  • 4 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£875
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering

Lockton, near Pickering, Yorkshire

Horcum View

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

4.9

out of 5

7 nights

From

£333
View

Dog Friendly Cottages in Pickering

Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.8

out of 5

7 nights

From

£493
View
Exterior | New Meadows Cottage, Pickering

Pickering, Yorkshire

New Meadows Cottage

Wifi
Car parking on site
Garden / Patio
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 2 pets allowed

2.8

out of 5

7 nights

From

£407
View
Reserve today for only £25
Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£575
View
Exterior | Evergreen Cottage, Sinnington, nr. Pickering

Sinnington, near Pickering, Yorkshire

Evergreen Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£423
View
Reserve today for only £25
Perfect holiday hideaway | Saltersgate - Hungate Cottages, Pickering

Pickering, Yorkshire

Hungate Cottages - Saltersgate

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 7
  • 4 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£875
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering

Lockton, near Pickering, Yorkshire

Horcum View

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

4.9

out of 5

7 nights

From

£333
View
Exterior | Featherstone Cottage, Newton-upon-Rawcliffe

Newton-upon-Rawcliffe, Yorkshire

Featherstone Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 10
  • 5 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£815
View
Reserve today for only 25%
Sands Farm Cottages - Fuchsia Cottage, Wilton near Pickering

Wilton near Pickering, Yorkshire

Sands Farm Cottages - Fuchsia Cottage

Hot Tub
Wifi
Car parking on site
  • Sleeps up to 2
  • 1 bedroom
  • 1 bathroom
  • Up to 1 pet allowed

4.3

out of 5

7 nights

From

£749
View
Reserve today for only £25
Exterior | Fox Cover Cottage, Little Edstone, near Pickering

Little Edstone, near Pickering, Yorkshire

Fox Cover Cottage

Wifi
Swimming pool
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£645
View
Reserve today for only £25
Lovely detached holiday home | Peasholm, Thornton le Dale, near Pickering

Thornton le Dale, near Pickering, Yorkshire

Peasholm

Enclosed Garden / Patio
Pub within 1 mile
Detached
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

3.4

out of 5

7 nights

From

£453
View
Reserve today for only £25
Exterior | Old Maltongate Farm Cottage, Thornton Le Dale

Thornton Le Dale, Yorkshire

Old Maltongate Farm Cottage

Wifi
Car parking on site
Detached
  • Sleeps up to 2
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£493
View
Reserve today for only £25

Luxury Cottages in Pickering

Living room | 4 Smiddy Hill, Pickering

Pickering, Yorkshire

4 Smiddy Hill

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

5

out of 5

7 nights

From

£559
View
Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£575
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

5

out of 5

7 nights

From

£705
View
Reserve today for only £25
Living room | Willowfield Cottage, Thornton-Le-Dale

Thornton-Le-Dale, Yorkshire

Willowfield Cottage

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

7 nights

From

£575
View
Exquisite holiday cottage | Cherry Laurel - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Laurel

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

4.6

out of 5

7 nights

From

£543
View
Exterior | Warrington House - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Warrington House

Luxury
Wifi
Enclosed Garden / Patio
  • Sleeps up to 9
  • 4 bedrooms
  • 4 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£765
View
Delightful single-storey holiday home | Newstead Cottage, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Newstead Cottage

Luxury
Wifi
Car parking on site
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£929
View
Living room | Warrington Mews - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Warrington Mews

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

5

out of 5

7 nights

From

£537
View
Exterior | Forge House, Thornton Le Dale, near Pickering

Thornton Le Dale, near Pickering, Yorkshire

Forge House

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

5

out of 5

7 nights

From

£513
View
Exterior | Trackside Cottage, Pickering

Pickering, Yorkshire

Trackside Cottage

Luxury
Wifi
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

5

out of 5

7 nights

From

£565
View
Delightful open-plan living space | West Wood Hideaway, Wrelton, near Pickering

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

7 nights

From

£363
View
Exquisite holiday cottage | Cherry Blossom - Cherry Garth Cottages, Thornton le Dale near Pickering

Thornton le Dale near Pickering, Yorkshire

Cherry Blossom

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

5

out of 5

7 nights

From

£523
View

Romantic Cottages in Pickering

Exterior | Mill Cottage, Pickering

Pickering, Yorkshire

Mill Cottage

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£795
View
Living room | Hallgarth House, Pickering

Pickering, Yorkshire

Hallgarth House

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 10
  • 5 bedrooms
  • 2 bathrooms
  • Up to 0 pets allowed

4.8

out of 5

7 nights

From

£845
View
Reserve today for only 25%
Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 1 pet allowed

4.8

out of 5

7 nights

From

£493
View
Living area | Higgledy Hideout, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, Yorkshire

Higgledy Hideout

Luxury
Wifi
Pub within 1 mile
  • Sleeps up to 5
  • 3 bedrooms
  • 2 bathrooms
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£575
View
Exterior | Evergreen Cottage, Sinnington, nr. Pickering

Sinnington, near Pickering, Yorkshire

Evergreen Cottage

Wifi
Enclosed Garden / Patio
Pub within 1 mile
  • Sleeps up to 4
  • 2 bedrooms
  • 1 bathroom
  • Up to 2 pets allowed

5

out of 5

7 nights

From

£423
View
Reserve today for only £25
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

5

out of 5

7 nights

From

£705
View
Reserve today for only £25
Perfect holiday hideaway | Saltersgate - Hungate Cottages, Pickering

Pickering, Yorkshire

Hungate Cottages - Saltersgate

Wifi
Car parking on site
Pub within 1 mile
  • Sleeps up to 7
  • 4 bedrooms
  • 2 bathrooms
  • Up to 1 pet allowed

5

out of 5

7 nights

From

£875
View
Pretty holiday bungalow  | Horcum View, Lockton, near Pickering

Lockton, near Pickering, Yorkshire

Horcum View

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

4.9

out of 5

7 nights

From

£333
View
Living room | Willowfield Cottage, Thornton-Le-Dale

Thornton-Le-Dale, Yorkshire

Willowfield Cottage

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

7 nights

From

£575
View
Exterior | Featherstone Cottage, Newton-upon-Rawcliffe

Newton-upon-Rawcliffe, Yorkshire

Featherstone Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • Sleeps up to 10
  • 5 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.6

out of 5

7 nights

From

£815
View
Reserve today for only 25%
Exterior | Fox Cover Cottage, Little Edstone, near Pickering

Little Edstone, near Pickering, Yorkshire

Fox Cover Cottage

Wifi
Swimming pool
Car parking on site
  • Sleeps up to 5
  • 3 bedrooms
  • 3 bathrooms
  • Up to 2 pets allowed

4.5

out of 5

7 nights

From

£645
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

Sign up for a chance to win £500!

Stay updated on the latest deals, exclusive offers and new holiday destinations by joining the cottages.com newsletter! Register today and automatically be entered into our prize draw to win a £500 voucher.

Click here for terms and conditions. You can opt out anytime by using the unsubscribe link in our emails. We will use your information as per our Privacy Notice.