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

Lovely stone-built holiday home | Daisy Cottage, Thornton-le-Dale

Thornton-le-Dale, North Yorkshire

Daisy Cottage

Wifi
Car parking on site
Rural Location
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.8

out of 5

7 nights

From

£393
View
Reserve today for only £25
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

4.8

out of 5

7 nights

From

£625
View
Reserve today for only £25
Living area | Stonecroft, Wrelton near Pickering

Wrelton near Pickering, North Yorkshire

Stonecroft

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£427
View
Reserve today for only £25
Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, North Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.8

out of 5

7 nights

From

£493
View
Reserve today for only £25
Lovely holiday home | Ash Garth Cottage, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Ash Garth Cottage

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 2 Bathrooms
  • 1 Pet

4.8

out of 5

7 nights

From

£585
View
Living room | Warrington Mews - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Warrington Mews

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£543
View
Reserve today for only £25
The Old King’s Head, Pickering

Pickering, North Yorkshire

The Old King’s Head

Wifi
Car parking on site
Pub within 1 mile
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£527
View
Southolme Lodges - Elm Lodge, Pickering

Pickering, North Yorkshire

Southolme Lodges - Elm Lodge

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

4.6

out of 5

7 nights

From

£297
View
Reserve today for only £25
Exterior | Old Barn Cottage, Lockton near Pickering

Lockton near Pickering, North Yorkshire

Old Barn Cottage

Wifi
Car parking on site
Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£427
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

£595
View
Reserve today for only £25
Open plan living space | Oak Lodge - Southolme Lodges, Pickering

Pickering, North Yorkshire

Southolme Lodges - Oak Lodge

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

4.6

out of 5

7 nights

From

£287
View

Dog Friendly Cottages in Pickering

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

4.8

out of 5

7 nights

From

£625
View
Reserve today for only £25
Living area | Stonecroft, Wrelton near Pickering

Wrelton near Pickering, North Yorkshire

Stonecroft

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£427
View
Reserve today for only £25
Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, North Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.8

out of 5

7 nights

From

£493
View
Reserve today for only £25
Lovely holiday home | Ash Garth Cottage, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Ash Garth Cottage

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 2 Bathrooms
  • 1 Pet

4.8

out of 5

7 nights

From

£585
View
Living room/dining room | Levisham - Hungate Cottages, Pickering

Pickering, North Yorkshire

Hungate Cottages - Levisham

Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

7 nights

From

£765
View
Reserve today for only £25
Living room | Warrington Mews - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Warrington Mews

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£543
View
Reserve today for only £25
Exterior | Old Barn Cottage, Lockton near Pickering

Lockton near Pickering, North Yorkshire

Old Barn Cottage

Wifi
Car parking on site
Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£427
View
Reserve today for only £25
Semi-detached holiday cottage | Squirrel Cottage, Thornton-le-Dale

Thornton-le-Dale, North Yorkshire

Squirrel Cottage

Wifi
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

3.9

out of 5

7 nights

From

£237
View
Reserve today for only £25
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
Reserve today for only £25
Living room | Darla Cottage, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Darla Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£639
View
Reserve today for only £25
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

Luxury Cottages in Pickering

Lovely holiday home | Ash Garth Cottage, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Ash Garth Cottage

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 2 Bathrooms
  • 1 Pet

4.8

out of 5

7 nights

From

£585
View
Living room | Warrington Mews - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Warrington Mews

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£543
View
Reserve today for only £25
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 | 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

£595
View
Reserve today for only £25
Living room | Darla Cottage, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Darla Cottage

Luxury
Wifi
Enclosed Garden / Patio
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£639
View
Reserve today for only £25
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

£353
View
Reserve today for only £25
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

£457
View
Reserve today for only £25
Kitchen | 1 Chapel Terrace, Pickering

Pickering, North Yorkshire

1 Chapel Terrace

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

5

out of 5

7 nights

From

£353
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

£483
View
Reserve today for only £25
Exterior | Trackside Cottage, Pickering

Pickering, North Yorkshire

Trackside Cottage

Luxury
Wifi
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

5

out of 5

7 nights

From

£816
View
Living room | Box Tree Cottage, Pickering

Pickering, North Yorkshire

Box Tree Cottage

Luxury
Wifi
Car parking on site
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 1 Pet

4.9

out of 5

7 nights

From

£645
View
Reserve today for only £25

Romantic Cottages in Pickering

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

4.8

out of 5

7 nights

From

£625
View
Reserve today for only £25
Living area | Stonecroft, Wrelton near Pickering

Wrelton near Pickering, North Yorkshire

Stonecroft

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

5

out of 5

7 nights

From

£427
View
Reserve today for only £25
Exterior | Swallowdale Cottage, Levisham, near Pickering

Levisham, near Pickering, North Yorkshire

Swallowdale Cottage

Wifi
Car parking on site
Enclosed Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.8

out of 5

7 nights

From

£493
View
Reserve today for only £25
Lovely holiday home | Ash Garth Cottage, Little Barugh, near Pickering

Little Barugh, near Pickering, North Yorkshire

Ash Garth Cottage

Luxury
Wifi
Car parking on site
  • 2 Guests
  • 1 Bedroom
  • 2 Bathrooms
  • 1 Pet

4.8

out of 5

7 nights

From

£585
View
Living room/dining room | Levisham - Hungate Cottages, Pickering

Pickering, North Yorkshire

Hungate Cottages - Levisham

Wifi
Car parking on site
Pub within 1 mile
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • 1 Pet

7 nights

From

£765
View
Reserve today for only £25
Living room | Warrington Mews - Warrington Retreat, Thornton-le-Dale, near Pickering

Thornton-le-Dale, near Pickering, North Yorkshire

Warrington Mews

Luxury
Wifi
Car parking on site
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathroom
  • 1 Pet

4.9

out of 5

7 nights

From

£543
View
Reserve today for only £25
The Old King’s Head, Pickering

Pickering, North Yorkshire

The Old King’s Head

Wifi
Car parking on site
Pub within 1 mile
  • 7 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • 0 Pets

4.9

out of 5

7 nights

From

£527
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 | Old Barn Cottage, Lockton near Pickering

Lockton near Pickering, North Yorkshire

Old Barn Cottage

Wifi
Car parking on site
Garden / Patio
  • 2 Guests
  • 1 Bedroom
  • 1 Bathroom
  • 2 Pets

4.9

out of 5

7 nights

From

£427
View
Reserve today for only £25
Semi-detached holiday cottage | Squirrel Cottage, Thornton-le-Dale

Thornton-le-Dale, North Yorkshire

Squirrel Cottage

Wifi
Pub within 1 mile
Garden / Patio
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 1 Pet

3.9

out of 5

7 nights

From

£237
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

£595
View
Reserve today for only £25
Exterior | Archways - Loand House Court, Wrelton, near Pickering

Wrelton, near Pickering, North Yorkshire

Loand House Court - Archways

Wifi
Car parking on site
Pub within 1 mile
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • 0 Pets

7 nights

From

£865
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

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