Pickering

Pickering Holiday Cottages
Vale of Ryedale, North Yorkshire

Photo of Smiddy Hill Pickering with the church in the backgroundPickering is a historic market town and is well known as the ‘Gateway to the North York Moors’. The town is reputed to be one of the oldest towns in the area dating back to 270BC when founded by Peredurus – King of the Brigantes.

The magnificent spire of the Church of St Peter and St Paul dominates the skyline of Pickering. The church contains some remarkable 15th century murals. Above the town are the ruins of Pickering Castle which are steeped in royal history. Excellent panoramic views over the town can be seen from the highest point of the bailey of the castle.

Pickering is the southern terminus of the fantastic North Yorkshire Moors Railway. The train will take you on a relaxing ride through beautiful countryside on England’s longest steam railway. You can visit Levisham, Goathland, Grosmont and Whitby. It is a highly recommended excursion!

The Beck Isle Museum is an interesting place to visit if you wish to learn about local heritage, history and cultural life. Pickering is a good base for visiting many tourist attractions including Dalby Forest, Flamingo Land Theme Park, Helmsley Walled Garden, Castle Howard and the Yorkshire Heritage Coast. There is a superb choice of restaurants, cafes, shops and pubs in Pickering. Ideal for self catering holidays.

We have a wide range of Pickering Holiday Cottages for you, both in and the area around the town.

Pickering – Self Catering Accommodation

Please click through for more information, photos & reviews of these holiday cottages in Pickering.


Photo of Spire View ( Ref 943752 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireSpire View, Pickering – 943752
One bedroom – Sleeps 2

First floor holiday apartment set above a gift shop overlooking the main street in Pickering. Ideal central location for enjoying the town & exploring the area. Internal stairs lead up to cosy & comfortable self catering accommodation. Compact kitchen with dining area. Sitting room with views over town to church spire beyond. 1 twin bedroom. Shower room. Garden bench. Off road parking for 1 car in rear courtyard. Sorry no pets. N.B. adult guests only. Shop, pub, restaurant, Beck Isle Museum & Steam Railway 2 minutes’ walk.
More info…….!


Photo of Station View ( Ref 951135 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireStation View, Pickering – 951135
One bedroom – Sleeps 2

Contemporary first floor holiday apartment for two guests has a central location in Pickering. Homely property is set above a gift shop, overlooking market place & North Yorkshire Moors Steam Railway. Self catering accommodation with open plan living space: kitchen area, dining area & comfortable modern seating area. 1 twin bedroom. Shower room. Off road parking for 1 car. Sorry no pets. Shop & pub 3 minutes’ walk.
More info…….!


Photo of Railway Cottage Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireRailway Cottage, Pickering
Five bedrooms – Sleeps 11

Luxury period townhouse in central Pickering location facing market place & near to railway station. Property dates back to 1793 when the building was a Saddlers. Original features such as oak beams & inglenook fireplace have been restored & complement the contemporary decor & furnishings. Ground floor has open plan kitchen/dining area with wood-burner & generous lounge. 3 first floor double bedrooms & family bathroom. 2 second floor bedrooms: 1 twin & 1 double with additional single bed. Shower room. Charming patio to rear with furniture & barbecue. Off-road car parking. Sorry no pets. Short walk to Pickering amenities.
More info…….!


Photo of Beck Cottage ( Ref 24339 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireBeck Cottage, Pickering – 24339
Two bedrooms – Sleeps 4

Welcoming stone-built end-terrace corner holiday cottage near Pickering Railway Station – ideal for steam enthusiasts! Property has been renovated, retaining character with beams & stripped pine doors. Ground floor has galley-kitchen with dining area & sitting room has wood-burning stove & lovely view to railway yards. 2 first floor bedrooms: 1 king-size double & 1 twin. Bathroom. Patio with furniture. Off road parking for 1 car. Sorry no pets. Shop & pub 3 minutes’ walk. N.B. steep stairs, may be unsuitable for guests with limited mobility.
More info…….!


Photo of Pickering Beckside ( Ref UK2202 ) Pickering holiday cottage - Ryedale self catering accommodation in North YorkshirePickering Beckside, Pickering – UK2202
Three bedrooms – Sleeps maximum 5

Unique terraced holiday property, just round the corner from Pickering Railway Station. Tucked away in a quiet area yet short walk to main street amenities. Originally a work house serving the local mill this charming character property retains some of its original features. Accommodation is set over 3 floors. Ground floor has beamed living room & farmhouse style kitchen/dining room with Aga. Open tread stairs to 1 first floor double bedroom & bathroom. Second floor has 1 super king-size bedroom & 1 double bedroom. Small enclosed courtyard with sitting-out area & garden furniture. Roadside car parking. 1 pet welcome. Shop & pub 100 yards. Restaurant 150 yards.
More info…….!


Photo of Platform 2 & 3/4 Cottage ( Ref 903429 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshirePlatform 2 & 3/4 Cottage, Pickering – 903429
Three bedrooms – Sleeps 6

Stone-built terraced holiday cottage opposite Pickering Railway Station – ideal for steam enthusiasts! Property restored to offer stylish & comfortable accommodation. Ground floor has kitchen, cosy sitting room with dining area & wood-burner. 3 spacious bedrooms: 2 double & 1 twin (can be super king-size double). Bathroom. Small courtyard with furniture. Off road parking for 1 car (100 yards away). 2 well-behaved dogs welcome. Shop & pub 2 minutes’ walk.
More info…….!


Photo of The Sidings ( Ref 939239 ) Holiday cottage in Pickering Ryedale North Yorkshire - Self catering accommodationThe Sidings, Pickering – 939239
Three bedrooms – Sleeps 6

Cosy Grade II Listed holiday cottage set across the road from North Yorkshire Moors Railway station. Property was reputedly once a bakery & public house. Beamed self catering accommodation set over 3 floors: Kitchen with dining area. Sitting room. 3 bedrooms: 1 king-size double, 1 double & 1 second floor twin with sloping ceilings & open stairs (stairgate available). Bathroom. Attractive patio with furniture. Off road parking for 1 car. Sorry no pets. Pickering shops, pubs & restaurants 5 minutes’ walk.
More info…….!


Photo of Hallgarth House ( Ref ISE ) Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireHallgarth House, Pickering – ISE
Five bedrooms – Sleeps 10

Imposing Grade II Listed property in Pickering, oozes charm, character & elegance. Antique & reproduction furnishings & original artwork. Large living room with open fire, mullion windows & wooden floor. Sitting room with open fire. Spacious dining room. Well-equipped kitchen with Aga & breakfast area. Utility. Toilet. 5 bedrooms: 3 first floor: 1 (5ft) double & 2 twin. Bathroom. 2 second floor: 1 double & 1 twin. Bathroom. Enclosed lawned garden with furniture & barbecue. Secure bike store. Roadside car parking. Garage for small car or motorbike (300 yards). Sorry no pets. 5 minutes’ walk to Pickering market place. Shop 200 yards. Pub 150 yards.
More info…….!


Photo of Cardioid Cottage ( Ref UK2272 ) Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireCardioid Cottage, Pickering – UK2272
Two bedrooms – Sleeps 4

Centrally located holiday cottage in Pickering is tucked away in a quiet corner, yet close to town amenities. Property is thoughtfully furnished & is ideal for year round family holidays. Ground floor accommodation has living room with electric wood-burner & kitchen with dining area. 2 first floor bedrooms: 1 en-suite double & 1 twin. Bathroom. Enclosed courtyard with sitting-out area & garden furniture. Parking for 1 car. 1 pet welcome. Shops & restaurants 50 yards. Pubs 100 yards.
More info…….!


Photo of Forget-Me-Not Cottage ( Ref UK2314 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireForget-Me-Not Cottage, Pickering – UK2314
One bedroom – Sleeps 2

‘Upside down’ terraced holiday cottage is ideally located for Pickering attractions & amenities. Property has been carefully renovated & presented to a good standard. Ground floor accommodation has well-equipped kitchen, 1 double bedroom & separate toilet. First floor has living/dining room, inviting lounge with gas fire & shower room. On road car parking. Sorry no children under 16 & no pets. Shop & pub 200 yards. Restaurant 250 yards.
More info…….!


Photo of 22 Hungate ( Ref 957902 ) Pickering holiday cottage sleeps 4 - Self catering accommodation in Ryedale North Yorkshire22 Hungate, Pickering – 957902
Two bedrooms – Sleeps 4

Charming period holiday cottage set on ground floor of a converted property in Pickering, just a short stroll from town market place & amenities. Accommodation is stylishly appointed throughout & combines ‘olde worlde charm’ with contemporary comfort. Spacious kitchen with dining area. Welcoming sitting room with cosy electric fire. 2 bedrooms: 1 king-size double (zip & link – can be twin) with en-suite shower room & 1 double with en-suite bathroom. Off road parking for 1 car, approximately 200 yards away. Sorry no pets. Shop & pub 2 minutes’ walk.
More info…….!


Photo of Hungate Holiday Cottages in Pickering - Self catering accommodation sleeping up to 8 people - Rent holiday home in RyedaleHungate Cottages, Pickering
Two to Five bedrooms – Sleeps up to 12

A collection 11 lovely holiday cottages within a short stroll of town centre. Delightful setting includes award winning secluded gardens, courtyards & an orchard. Converted with flair from the outbuildings of Hungate House by the owners. Each cottage retains character, with old stone arches, fireplaces & beams. Immaculately maintained ‘home from home’ cottages, superbly well equipped. Children’s play area. Cycle storage. Parking. Pets at some properties.
More info…….!


Pickering Castle in North Yorkshire England

Visit Pickering Castle (English Heritage)


Photo of Hillcrest ( Ref CC233055 ) Ryedale holiday cottage in Pickering North Yorkshire - Self catering accommodation sleeps 4Hillcrest, Pickering – CC233055
Three bedrooms – Sleeps 4

Peacefully located spacious Edwardian house in heart of Pickering. Modernised traditional property provides good holiday accommodation for both families & couples. Ground floor has kitchen/diner. Cosy lounge with log burning stove. Utility room. Cloakroom. Garden room with dining area. 3 first floor bedrooms: 1 double & 2 single. Bathroom. Enclosed garden with furniture. Bike storage available. On street car parking. Sorry no pets. Shops & pub 200 yards, restaurant 500 yards.
More info…….!


Photo of Bow Cottage ( Ref 24977 ) Pickering self catering holiday accommodation in Ryedale North YorkshireBow Cottage, Pickering – 24977
Three bedrooms – Sleeps 6

200-year-old terraced stone holiday cottage overlooking Smiddy Hill green, close to Pickering town centre. Property is full of charm & character. 2 living rooms (1 with double sofa bed for alternative sleeping), dining room & kitchen. Shower room with toilet. 3 bedrooms: 1 ground floor double with beams. 2 first floor bedrooms: 1 king-size double & 1 twin. Enclosed lawned garden with patio, sitting-out area, furniture, summer house & barbecue. Parking for 2 cars. Sorry no pets. Shops, restaurants & pubs 50 yards.
More info…….!


Photo of La Fenetre Cottage ( Ref 952998 ) Pickering holiday cottage sleeps 5 - Self catering accommodation in Ryedale North YorkshireLa Fenetre, Pickering – 952998
Three bedrooms – Sleeps 5

Cosy & inviting semi-detached property in Pickering is set over 3 floors. Newly renovated accommodation: Ground floor has beamed open plan living space with comfy seating area, traditional dining area & homely kitchen area with breakfast bar. Wooden stairs to 1 beamed double bedroom & 1 step to second en-suite double bedroom. Curved stairway to 1 en-suite twin bedroom with beams & low ceilings. Courtyard patio to front with furniture (N.B. front courtyard is close to main road). Free roadside car parking 50 yards – first come, first served. Public car park 50 yards. 1 well-behaved pet welcome. Shop & pub 5 minutes’ walk.
More info…….!


Photo of The Old Kings Head ( Ref CC233034 ) Rent holiday cottage in Pickering - Accommodation close to town centreThe Old King’s Head, Pickering – CC233034
Three bedrooms – Sleeps 7

Spacious holiday cottage, formerly an 18th Century inn, provides comfortable accommodation for families & couples. Sits in quiet courtyard just 50 yards from Pickering town centre. Property is furnished & decorated to high standard. Ground floor has cosy living room with multi-fuel stove. Kitchen/diner. 3 bedrooms: First floor has 1 king-size & 1 twin. First floor bathroom. Second floor has 1 en-suite bedroom with king-size cast-iron bed, single bed & travel cot. Children’s play area in basement. Parking for 2 cars in courtyard. Sorry no pets.
More info…….!


Holiday cottage in Pickering North Yorkshire - Ivy House ( Ref DC5276 ) Holiday home sleeps 10 guestsIvy House, Pickering – DC5276
Five bedrooms – Sleeps 10

Beautifully presented holiday property, dating back to 1820’s, set within a short stroll of Pickering’s amenities & attractions. Elegantly furnished accommodation set over 3 floors – ideal for large groups & families! Ground floor has spacious dining kitchen with breakfast bar, dining room & sitting room, both with gas ‘flame-effect’ fire. Cloakroom. 4 first floor bedrooms: 2 en-suite, both with king-size sleigh bed, 1 twin, 1 with twin & single pull-out bed & bathroom. Narrow staircase to second floor with dressing area & bedroom with 2 double beds. Bathroom. Lawned garden, patio & furniture (N.B. covered well in grounds). Private parking for 3 to 4 cars. Sorry no pets.
More info…….!


Self catering holiday home in Pickering - Four Seasons ( Ref CC233116 ) holiday cottage sleeps 6 peopleFour Seasons, Pickering – CC233116
Three bedrooms – Sleeps 6

Lovingly restored charming holiday cottage, set in the heart of Pickering. Four Seasons has modern facilities with the ambience of a traditional country cottage. Ground floor accommodation has beamed lounge/dining room with oak floor & multi-fuel burner, kitchen & cloakroom. 3 bedrooms: Steep narrow stairs to first floor with 1 king-size, 1 twin & bathroom, steep narrow stairs to second floor en-suite king-size. Enclosed courtyard with sitting out area, furniture & barbecue. Parking for 1 car. 2 pets welcome. Restaurants, pubs & shops nearby.
More info…….!


Photo of Rose Cottage ( Ref UK2409 ) Pickering holiday cottage sleeps 4 - Ryedale self catering accommodation in North YorkshireRose Cottage, Pickering – UK2409
Two bedrooms – Sleeps 4

Traditional terraced holiday cottage in Pickering. Rose Cottage has been thoughtfully furnished & has some lovely features. Accommodation is set over 3 floors. 2 steps to entrance. Ground floor has cosy beamed living room with wood-burner & kitchen/dining room with beams. First floor has beamed double bedroom & bathroom. Steep stairs to second floor twin bedroom with beams. Enclosed courtyard with sitting-out area & garden furniture (N.B. 2 steps in garden). Bike store. Parking for 1 car. 1 small dog welcome. Shop 100 yards, pub 200 yards & restaurant 50 yards.
More info…….!


Photo of Westgate Cottage ( Ref 904479 ) Rent Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireWestgate Cottage, Pickering – 904079
Two bedrooms – Sleeps 4

Comfortable semi-detached holiday cottage, which adjoins the owners’ home & bed/breakfast, set back from the main A170 road. 10 minutes’ walk from Pickering market place, shops & attractions. Well-equipped bright & airy holiday property with open plan living space with kitchen, dining area & comfy sitting area with electric fire. External utility. 2 bedrooms: 1 double & 1 twin. Bathroom. Front & rear shared gardens with furniture. Lockable cycle store. Off road parking for 1 car. Sorry no pets. Shop 5 minutes’ walk, pub 2 minutes’ walk. Good base for exploring moors & coast.
More info…….!


Photo of Lockton Cottage ( Ref 920887 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireLockton Cottage, Pickering – 920887
Two bedrooms – Sleeps 4

Beautifully presented Grade II Listed end terrace stone-built holiday cottage in Pickering. Property is renovated to high standard & tastefully furnished. Ground floor has bright, modern kitchen with small dining area & cosy beamed sitting room with open fire in original fireplace. Fairly steep cottage stairs to 2 first floor bedrooms: 1 double & 1 twin. Bathroom. 2 steps to enclosed lawned garden with patio & furniture. Off road parking for 2 cars. Sorry no pets. 10 minutes’ walk to Pickering town centre amenities, pub 3 minutes’ walk. N.B. cottage is on main A170 road but is secondary glazed.
More info…….!


Photo of Cosy Cottage ( Ref 963828 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireCosy Cottage, Pickering – 963828
Two bedrooms – Sleeps 3

Delightful character mid-terrace Pickering holiday cottage. Beautifully decorated self catering accommodation with homely features – ideal romantic retreat for a couple or for a small family! Ground floor has well-equipped kitchen with feature cast-iron bakers oven, sitting room with dining area & open fire in original cast-iron fireplace. Shower room. 2 bright & airy first floor bedrooms: 1 super king-size double (zip & link – can be twin) & 1 single. Enclosed rear lawned garden with patio area, furniture, barbecue & summerhouse. Bike store. Off road parking for 1 car. Sorry no pets. Pub 2 minutes’ walk.
More info…….!


Photo of The Old Cartway ( Ref 964829 ) Rent Pickering holiday home sleeps 6 - Ryedale self catering accommodation in North YorkshireThe Old Cartway, Pickering – 964829
Four bedrooms – Sleeps 5-6

Charming mid-terrace stone-built holiday cottage in Pickering. Ground floor accommodation has well-equipped kitchen, adjoining dining room with garden views, utility area, homely sitting room with exposed beams & period open fire, 1 snug/single bedroom & shower room. Original wooden staircase to 3 first floor bedrooms: 1 double, 1 adult bunks & 1 single. Bathroom. Ramp access from the rear. Enclosed rear lawn & patio with furniture. Lockable shed. Off road parking for 1 car. 1 well-behaved dog welcome. Pub 2 minutes’ walk. Shop 10 minutes’ walk.
More info…….!


Photo of Pickering Railway Station - Home of the North Yorkshire Moors Railway

Enjoy a trip on the popular North Yorkshire Moors Railway


Photo of Castlegate Cottage ( Ref 921306 ) Stay in Pickering holiday cottage sleeps 5 - Self catering accommodation in North YorkshireCastlegate Cottage, Pickering – 921306
Three bedrooms – Sleeps 5

Pretty stone-built Grade II Listed terrace holiday cottage near Pickering Castle. Tastefully furnished property with painted beams. Ground floor accommodation has spacious open plan living space with modern kitchen, dining area & sitting area with cosy wood-burner. 3 first floor bedrooms: 1 double, 1 twin with views over rooftops & 1 single. Bathroom. Small enclosed walled yard. Roadside parking 50 yards from cottage – first come, first served. 1 well-behaved dog welcome. Shop & pub 10 minutes’ walk.
More info…….!


Photo of Keep Cottage ( Ref 904784 ) Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireKeep Cottage, Pickering – 904784
Three bedrooms – Sleeps 5

17th Century mid-terrace, period holiday cottage oozes charm & character. Property is stylishly appointed throughout. Ground floor accommodation has a well-equipped kitchen with dining area set in brick alcove & sitting room with cosy wood-burning stove. 3 first floor bedrooms: 1 double with en-suite shower room, 1 twin & 1 single. Bathroom. Conservatory leads to enclosed lawned cottage garden with patio, furniture & barbecue. Bike storage. Roadside parking outside cottage. 1 well-behaved dog welcome. Shop & pub 5 minutes’ walk.
More info…….!


Photo of 12 Castlegate ( Ref 954083 ) Pickering holiday cottage North Yorkshire12 Castlegate, Pickering – 954083
Two bedrooms – Sleeps 3-4

Attractive character Grade II Listed terraced holiday cottage in Pickering. Set in quiet location with a short walk to Pickering Castle. Property is tastefully furnished & decorated with a homely feel. Ground floor accommodation has cosy sitting room with beamed ceilings & open fire, separate dining room, modern kitchen & bathroom. 2 first floor bedrooms: 1 double & 1 single with pull-out bed. Private enclosed garden with furniture. Bike store. Roadside car parking – first come, first served. 1 well-behaved dog welcome. Gentle stroll down to Pickering amenities.
More info…….!


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Enjoy your holiday cottage in Pickering, North Yorkshire!

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