A locomotive hauls a carriage set through open countryside.

Find My Favourite Holiday Cottages in Pickering

Pickering is an ancient market town on the southern edge of the dramatic North York Moors. Holiday cottages in Pickering tend to be within a comfortable stroll of the town centre, which is home to several cosy pubs and excellent eateries – including Willowgate Bistro, Feast and local favourite Capplemans Fish and Chip Restaurant. With its famous Medieval wall paintings, traditional railway and stunning views across the Vale of Pickering, this traditional community has plenty to offer visitors. Pickering is the perfect base for experiencing life in an authentic Yorkshire town and exploring some of the region’s most impressive countryside. At the heart of Pickering is a pretty marketplace where various independent businesses sell everything from fresh, local produce to gifts and antiques.

The North Yorkshire town of Pickering is situated on the edge of the North Yorkshire Moors, between the towns of Scarborough, Whitby, Helmsley and Malton and is often referred to as the “Gateway to the North York Moors”. The scenery around Pickering is spectacular, and it’s not just about the Moors. The region is full of historical places of interest and ancient Abbeys and houses to explore.

Single storey of a barn conversion overlooking a lawn on a North Yorkshire farm.
Sleeps
2
Bedrooms
1

The Smithy at Keld Head Cottages is a quaint romantic cottage on a gorgeous property outside Pickering in North Yorkshire. The rural holiday cottage boasts exposed beams, a traditional fireplace, award-winning gardens, beautiful views, and extensive indoor and outdoor play areas.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Cycling Holidays
  • Eco Cottages
  • Farm Cottages
  • Independent Cottages
  • Large Cottage Discounts
  • Remote Cottages
  • Romantic Cottages
  • Short Breaks
  • Small Cottages
  • Walking Holidays
A large, single storey barn conversion overlooks a lawn.
Sleeps
7
Bedrooms
3

Find warm accommodation for your Yorkshire holiday at The Stables at Keld Head Cottages, one of nine traditional cottages on the edge of the market town of Pickering, North Yorkshire, retaining much of the converted stone-built barn’s original features, with open beamed ceilings and stone fireplace.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Farm Cottages
  • Independent Cottages
  • Short Breaks
  • Walking Holidays
Barn conversions in a courtyard overlook a raised flower bed in its centre
Sleeps
5
Bedrooms
2

Tucked in near the Great Fryup Dale in the heart of North York Moors National Park, The Byre in the civil parish of Danby, North Yorkshire, sits on a working organic farm, a two-storey countryside cottage featuring exposed beams, vaulted ceiling, and ground floor underfloor heating.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Cycling Holidays
  • Farm Cottages
  • Independent Cottages
  • Short Breaks
  • Walking Holidays
Exterior ofa barn conversion behind a shrub-filled garden.
Sleeps
5
Bedrooms
2

One of nine countryside cottages that make up Keld Head Farm Cottages and nestled near the foot of rolling moorlands, Pigeon Cote near the market town of Pickering, North Yorkshire, retains much of its original charm and features, with open beamed ceilings and traditional stone fireplace.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Farm Cottages
  • Independent Cottages
  • Small Cottages
Exterior of a barn conversion overlooking a garden courtyard
Sleeps
8
Bedrooms
4

Pasture View Cottage is a large eco-friendly, single-storey country cottage on the edge of Pickering for holidays exploring the North York Moors and the North Yorkshire coast. Features include a large private garden and a very well-equipped kitchen. Children will love the play area and play shed.

  • Accessible By Train
  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Eco Cottages
  • Independent Cottages
  • Large Holiday Cottages
  • Short Breaks
  • Walking Holidays
A lounge with armchairs, oak-beamed ceiling and a staircase.
Sleeps
2
Bedrooms
2

Mill Cottage is a multi-award-winning property set on Keld Head Cottages near Pickering in North Yorkshire. The stone-built rural cottage has been carefully refurbished with traditional features and modern comforts and boasts gorgeous gardens, large indoor and outdoor play areas and lovely views.

  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Farm Cottages
  • Independent Cottages
  • Romantic Cottages
  • Small Cottages
Exterior of a large barn conversion with external steps to 1st flor front door - facing a mature garden
Sleeps
4
Bedrooms
2

The upside-down design of Barn Cottage captures the beautiful views of the Yorkshire countryside and adds another feature to this award-winning holiday cottage near Pickering. The rural cottage offers extensive manicured gardens with multiple play areas and spaces to entertain, relax, and unwind.

  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Farm Cottages
  • Independent Cottages
  • Romantic Cottages
  • Short Breaks
  • Small Cottages
  • Walking Holidays
Sleeps
4
Bedrooms
2

Owl is a two-bedroom apartment on the ground floor beneath Granary. It has two bedrooms, a double and a twin, and an open-plan living area with a fitted kitchen, lounge, and dining area. The apartment also has a shared indoor heated pool, spa, and sauna. Well-behaved dogs are welcome.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Cottages with Hot Tubs
  • Countryside Cottages
  • Dog-Friendly Holiday Cottages
  • Holiday Cottages With a Pool
  • Independent Cottages
  • Small Cottages
Sleeps
19
Bedrooms
10

Mel House Cottages are a group of four pet-friendly properties that sleep from 3 to 19 Guests in the centre of attractive Newton-on-Rawcliffe in the North York Moors. Three of the four properties are rated at various levels of accessibility for disabled use. Facilities include an indoor Pool, Hot Tub, and Sauna.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Countryside Cottages
  • Dog-Friendly Holiday Cottages
  • Holiday Cottages With a Pool
  • Independent Cottages
  • Large Holiday Cottages
  • Short Breaks
  • Walking Holidays

Stays in Pickering holiday homes would be incomplete without a trip to one of the town’s most celebrated historical attractions, the 15th-century wall paintings at St Peter and St Paul’s Church. Nearby is the imposing motte-and-bailey fortification of Pickering Castle, which dates back to the days of William the Conqueror and is open for visitors to explore. Taking a ride on a North Yorkshire Moors Railway steam locomotive is a magical way to experience the area’s breathtaking scenery. Trains run regularly from Pickering to Grosmont – and as far as the coastal town of Whitby during the summer. Enjoy an unforgettable meal on the Pullman Dining Train while 24 miles of glorious countryside float by. 

If you want to explore the windswept beauty of the North York Moors National Park, holiday cottages in Pickering are ideally located at the southern boundary. Wild moorlands, ancient abbeys, tumbling rivers and pretty villages can all be found in the park, which is a long-running favourite among ramblers and wildlife watchers.