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.

13 rental properties

Low Moor Holiday Cottages, Scarborough, Yorkshire, Northern England, England

4 bedroom Cottage, Pickering near Scarborough 4 miles away

sleeps 2 - 6 guests
2 - 6
4 bedrooms
4
1 bathrooms
1
no dogs allowed

A collection of 4 high quality country cottages nestled by rolling farmlands and countryside within the gorgeous North Yorkshire Moors National Park, 4 star rated and with WiFi internet access, these cottages are wonderful for peaceful rural retreat breaks and are just 5 miles from Scarborough.

Special features: free internet access.

Weekly Price from: £250

The Sands - Sea Front Apartments, Scarborough, Yorkshire, Northern England, England

3 bedroom Cottages, Pickering near Scarborough 5 miles away

sleeps 1 - 6 guests
1 - 6
3 bedrooms
3
2 bathrooms
2
no dogs allowed
5 star

A collection of award winning holiday apartments right by the seafront on Scarborough's blue flag award winning North Bay beach, with high quality interiors and a location like this, these are very special holiday homes.

Special features: free internet access, Gold Award Winning Cottage.

Weekly Price from: £400

Coastal Cottage near the Quayside, Scarborough, Yorkshire, Northern England, England

4 bedroom Coastal Cottage, Pickering near Scarborough 5 miles away

sleeps 4 - 9 guests
4 - 9
4 bedrooms
4
2 bathrooms
2
no dogs allowed
4 star

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.

Special features: games room.

Weekly Price from: £490
Next availability:
from 20 September to 21 September 20 from 09 October to 16 October 20

Dairy Countryside Cottage, North York Moors National Park, Staintondale, Yorkshire, Northern England, England

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

sleeps 1 - 2 guests
1 - 2
1 bedrooms
1
1 bathrooms
1
no dogs allowed
5 star

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.

Weekly Price from: £348
Next availability:
from 30 October to 20 November 20 from 27 November to 24 December 20

Bay Dream Modern Pet-Friendly Cottage, North York Moors & Coast, Filey, Yorkshire, Northern England, England

2 bedroom Cottage, Pickering near Scarborough 9 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
4 star

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.

Special features: pool (), tennis court, sauna.

Weekly Price from: £265
Next availability:
from 04 October to 05 October 20 from 09 October to 10 October 20

Maris Holiday Cottage, North Yorkshire Coast, Filey, Yorkshire, Northern England, England

4 bedroom Holiday Cottage, Pickering near Scarborough 10 miles away

sleeps 4 - 8 guests
4 - 8
4 bedrooms
4
2 bathrooms
2
dog-friendly cottage, 1 dog(s) welcome
1
4 star

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.

Special features: free internet access, pool (), tennis court, sauna.

Weekly Price from: £422
Next availability:
from 12 October to 16 October 20 from 02 November to 19 December 20

Mel House Cottages (Swimming Pool, Spa, Sauna), Pickering near Scarborough, Yorkshire, Northern England, England

10 bedroom Bungalow

sleeps 1 - 19 guests
1 - 19
10 bedrooms
10
6 bathrooms
6
dog-friendly cottage, 4 dog(s) welcome
4

A delightful collection of 4 star rated holiday cottages (including 2 wheelchair accessible cottages; 'Mallard' and 'Swift' have been M3 rated), in a pretty village location within the North York Moors National Park boasting excellent shared leisure facilities of an indoor heated pool, spa and sauna, exclusive to guests.

Special features: free internet access, pool (A heated swimming pool in the Leisure Suite on-site. It is 1.2 metres deep throughout, is roughly 6 metres long by 3 metres wide, and has a counter-current device permitting swimming 'on the spot'. ), games room, indoor hot tub, sauna.

Weekly Price from: £300

High Mill House, Pickering near Scarborough, Yorkshire, Northern England, England

4 bedroom Unique Holiday House

sleeps 6 - 12 guests
6 - 12
4 bedrooms
4
5 bathrooms
5
no dogs allowed

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).

Special features: free internet access.

Weekly Price from: £1236
Next availability:
from 19 September to 24 September 20 from 02 October to 24 October 20

Smithy Cottage, Filey, Yorkshire, Northern England, England

2 bedroom Cottage, Pickering near Scarborough 12 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
dog-friendly cottage, 3 dog(s) welcome
3

Unique 2 bedroom historical cottage with enclosed patio garden which was originally a blacksmiths, situated in a lovely rural hamlet close to Filey and Bridlington.

Special features: free internet access.

Weekly Price from: £250
Next availability:
from 25 September to 03 October 20 from 04 October to 05 October 20

The Old Watchmaker's Cottage, Cropton, Yorkshire, Northern England, England

1 bedroom Romantic Retreat, Pickering near Scarborough 14 miles away

sleeps 1 - 2 guests
1 - 2
1 bedrooms
1
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
3 star

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

Weekly Price from: £240
Next availability:
from 30 October to 06 November 20 from 20 November to 29 December 20

1 Corner Cottages, Dogs-welcome, North York Moors and Coast , Cropton, Yorkshire, Northern England, England

2 bedroom Cottage, Pickering near Scarborough 14 miles away

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
dog-friendly cottage, 1 dog(s) welcome
1
3 star

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.

Weekly Price from: £275
Next availability:
from 02 October to 03 October 20 from 20 November to 27 November 20

River Bank Cottage, Whitby, Yorkshire, Northern England, England

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

sleeps 1 - 4 guests
1 - 4
2 bedrooms
2
1 bathrooms
1
no dogs allowed
5 star

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.

Special features: free internet access.

Weekly Price from: £450


Special Offer: from 26 September to 03 October 20
Late availability: from 26 September to 03 October 20