Self catering holiday cottage rentals in Pickering near Scarborough, Yorkshire, England

Pickering is a picturesque market town, located at the edge of the North York Moors National Park.  By virtue of its location, Pickering is sometimes referred to as the ‘Gateway to the North Yorkshire Moors’.  Excellent opportunities for walking, cycling and wildlife watching await visitors to the National Park.  Pickering could be an obvious choice for a country holiday but did you know that the coast at Scarborough is just 18 miles away?  What’s more with the historical city of York being just 27 miles from Pickering, this could be an excellent location for a varied self-catering holiday in Yorkshire. 

What Pickering near Scarborough, Yorkshire offers for Self-Catering Holidays


In Pickering itself whilst on a cottage holiday you can catch a ride on the North York Moors Steam Railway which takes visitors through some spectacular scenery in the North Yorkshire Moors on a steam train.  Just a short drive from Pickering, at Hemsley you will find Helmsley Walled Garden with its stunning collection of colourful flowers and plants.  Helmsley Walled Garden is open to visitors between March and October and admission charges apply. 

Whether you are looking for a mansion to rent or a small romantic cottage for two, we trust that you will enjoy browsing through the choices available here.  We hope you find good quality self-catering accommodation to meets your needs in or near Pickering.

Book a Pickering near Scarborough cottage and look forward to discovering some of the best of Yorkshire on holiday.

15 rental properties

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Price from: £525
Next available: 11th Mar to 20th May 22
5 star
sleeps 3 - 6 guests 3 - 6
3 bedrooms 3
3 bathrooms 3
no dogs allowed

3 bedroom Georgian Cottage, Pickering near Scarborough 13 miles away

Lovely family-friendly and dog-friendly 3 bedroom holiday cottage which features a charming interior and a romantic four poster bed in one of the bedrooms, situated by the village green in the village of Fylingthorpe in the North York Moors National Park.

Facilities & Features: TVFree Wifi
Price from: £401
Next available: 4th Feb to 13th May 22
5 star
sleeps 2 - 5 guests 2 - 5
2 bedrooms 2
2 bathrooms 2
no dogs allowed

2 bedroom Holiday Apartment, Pickering near Scarborough 4 miles away

Elegant and stylish 2 bedroom 2 bathroom holiday apartment in seaside town of Scarborough.

Facilities & Features: Free Wifi
Price from: £611
Next available: 29th Jan to 11th Feb 22
4 star
sleeps 4 - 8 guests 4 - 8
4 bedrooms 4
2 bathrooms 2
dog-friendly cottage, 1 dog(s) welcome1

4 bedroom Holiday Cottage, Pickering near Scarborough 10 miles away

Escape to the North Yorkshire Coast for a relaxing break with a stay in this appealing 4 bedroom dog-friendly cottage, situated within a holiday village just 3 miles from the coastal town of Filey, close to the North York Moors National Park, the facilities on site include a swimming pool, sauna, steam room and gym.

Facilities & Features: TVFree WifiSaunaOwn swimming pool ()Tennis court
Price from: £361
Next available: 4th Feb to 18th Feb 22
3 star
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

2 bedroom Cottage, Pickering near Scarborough 14 miles away

Picturesque, dog and family friendly country hideaway with beautiful gardens, located in the village of Cropton in the North York Moors National Park, perfect for discovering the charming towns and villages of the moors, for visiting Helmsley Walled Garden, Duncombe Park's fantastic gardens and for visiting the historical city of York for a day trip This stone built cottage is located in the village of Cropton in the North Yorks Moors and can sleep four people in two bedrooms.

Facilities & Features: TV
Price from: £340
Next available: 11th Feb to 11th Mar 22
4 star
sleeps 1 - 5 guests 1 - 5
3 bedrooms 3
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

3 bedroom Holiday Bungalow, Pickering near Scarborough 16 miles away

3 bedroom pet-friendly cottage in village in the North York Moors National Park, sleeping up to 5 people, just 7 miles from Whitby.

Facilities & Features: TV
Price from: £373
Next available: 29th Jan to 11th Feb 22
5 star
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
no dogs allowed

1 bedroom Stone-Built Holiday Cottage, Pickering near Scarborough 9 miles away

Stylish one bedroom holiday barn situated close to Staintondale, with a Whirlpool bath and king-size bed plus a location close to the coast within the North York Moors National Park, this is a great place for a romantic break for two.

Facilities & Features: TV
Price from: £297
Next available: 31st Jan to 4th Feb 22
3 star
sleeps 1 - 2 guests 1 - 2
1 bedrooms 1
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

1 bedroom Romantic Retreat, Pickering near Scarborough 14 miles away

Pretty one bedroom stone-built holiday cottage with a village setting within the North York Moors National Park, ideal for romantic breaks.

Facilities & Features: TV
Price from: £730
Next available: 2nd Sep to 23rd Sep 22
4 star
sleeps 3 - 6 guests 3 - 6
3 bedrooms 3
2 bathrooms 2
dog-friendly cottage, 1 dog(s) welcome1

3 bedroom Coastal Cottage, Pickering near Scarborough 19 miles away

Quaint and lovely 3 bedroom pet-friendly coastal cottage in village of Sandsend, with fabulous coastal views from patio, just 3 miles from Whitby.

Facilities & Features: Free Wifi
Price from: £582
Next available: 4th Feb to 18th Feb 22
4 star
sleeps 4 - 9 guests 4 - 9
4 bedrooms 4
2 bathrooms 2
no dogs allowed

4 bedroom Coastal Cottage, Pickering near Scarborough 5 miles away

Holiday in Scarborough in a secluded setting, just moments from the seafront and a short walk from the beach, with spacious rooms, a games room with snooker table and a lovely enclosed courtyard garden, this beautifully presented 4 bedroom cottage is well placed for discovering the delights of Scarborough and the nearby North York Moors National Park.

Facilities & Features: TVGames room
Price from: £345
Next available: 30th Jan to 4th Feb 22
4 star
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
dog-friendly cottage, 1 dog(s) welcome1

2 bedroom Cottage, Pickering near Scarborough 9 miles away

High quality 2 bedroom dog-friendly holiday cottage with own garden situated just 3 miles from Filey on the North Yorkshire coast and close to the North York Moors National Park, located on a holiday development where guests benefit from access to excellent shared leisure facilities on site including an indoor swimming pool, gym and sauna.

Facilities & Features: TVSaunaOwn swimming pool ()Tennis court
Price from: £450
Next available: 31st Jan to 2nd Apr 22
5 star
sleeps 1 - 4 guests 1 - 4
2 bedrooms 2
1 bathrooms 1
no dogs allowed

2 bedroom Cottage by the Riverbank, Pickering near Scarborough 16 miles away

Escape for a romantic break or tranquil holiday in this delightful 2 bedroom holiday home, with a riverside garden this is a great place for a fishing break or take it easy holiday in Whitby and is conveniently close to the North York Moors National Park and the North Yorkshire Coast.

Facilities & Features: TVFree Wifi
Sorry, this owner/agency has not provided full pricing information.
Price from: £1626
Next available: -
sleeps 6 - 12 guests 6 - 12
4 bedrooms 4
5 bathrooms 5
no dogs allowed

4 bedroom Unique Holiday House

Attached to a historic water mill in Pickering, this roomy 4 bedroom holiday house offers unnrivalled views of the historic North York Moors Steam Railway which passes right past the house (sorry no pets permitted).

Facilities & Features: TVFree Wifi