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.

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
A semi-detached cottage overlooks a stone-walled front garden.
Sleeps
4
Bedrooms
2

The quaint Grade-II listed Croft Head Cottage boasts exposed beamed ceilings, flagged floors and a wood-burning stove in a converted coaching inn close to the village of Wrelton in the North York Moors. The pet-free property welcomes families with two bedrooms and cast-iron furnishings.

  • Active Holidays
  • Agency Cottages
  • Child-Friendly Cottages
  • Countryside Cottages
  • Small Cottages
Sleeps
10
Bedrooms
4

Boundcliffe is a large holiday cottage in a rural location in North Yorkshire Moors. It sleeps ten people in four bedrooms in the village of Allerston near Pickering. It is a spacious, traditional Farmhouse that makes a marvellous countryside base for families or friends. Pets are welcome.

  • Active Holidays
  • Agency Cottages
  • Child-Friendly Cottages
  • Cottages With Games Rooms
  • Countryside Cottages
  • Cycling Holidays
  • Dog-Friendly Holiday Cottages
  • Farm Cottages
  • Large Holiday Cottages
  • Short Breaks
  • Walking Holidays
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
2-storey exterior of. stone-built barn conversion overlooking a paved terrace and a lawn
Sleeps
2
Bedrooms
1

Harvest Cottage welcomes couples to a pretty stone and pantiled farm cottage near Pickering in the heart of picturesque Levisham. The pet-friendly, one-bedroom barn conversion offers ample gardens and peace and quiet. It is an ideal base for exploring the North York Moors and coast.

  • Active Holidays
  • Agency Cottages
  • Coastal Cottages
  • Countryside Cottages
  • Dog-Friendly Holiday Cottages
  • Farm Cottages
  • Romantic Cottages
  • Small Cottages
A heated indoor pool and large jacuzzi.
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
A chapel conversion with a large rose window sits behind a low stone wall.
Sleeps
8
Bedrooms
4

The Old Methodist Chapel is a sophisticated conversion of the old chapel in Rosedale Abbey. Set amid the North York Moors and Coast, the cottage features tall arched windows, exposed timbers, stripped pine doors, a cast iron and marble fireplace, a furnished sunny patio, and an open fire.

  • Active Holidays
  • Agency Cottages
  • Child-Friendly Cottages
  • Countryside Cottages
  • Cycling Holidays
  • Large Holiday 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
An indoor heated swimming pool at a Pickering holiday cottage
Sleeps
5
Bedrooms
3

Swift Cottage is a charming 3-bedroom ground floor cottage sleeping 5 with the use of an outdoor heated pool. The cottage has an easy-access wet room with rails and a mobility chair, so accessible for guests with disabilities. Swift is in the North York Moors National Park. Pets welcome.

  • Accessible Cottages
  • Active Holidays
  • Child-Friendly Cottages
  • Cottages with Hot Tubs
  • Countryside Cottages
  • Cycling Holidays
  • Dog-Friendly Holiday Cottages
  • Holiday Cottages With a Pool
  • Independent 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.