Pickering Holiday Cottages
Vale of Ryedale, North Yorkshire

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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. The Kirk Theatre has numerous events and productions throughout the year. 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

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

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View more cottages – Pickering Holiday Cottages – Page 2

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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 for 2 guests set above a gift shop overlooking the main street in Pickering. Spire View has an ideal central location for enjoying the town & exploring the area. 2 flights of internal stairs (may not be suitable for those with mobility issues) lead up to cosy & comfortable self catering accommodation. Compact kitchen with dining area. Sitting room with views over town to the 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 & North Yorkshire Moors Railway 2 minutes’ walk.
More info…….!

Spire View ( Ref 943752 ) Pickering North Yorkshire    Spire View Pickering ( Ref 943752 ) North Yorkshire holiday cottage sleeps 2    Spire View ( Ref 943752 ) Pickering holiday cottage rental for 2 guests

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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 2 guests has a central location in Pickering. Homely Station View is set above a gift shop, overlooking market place & North Yorkshire Moors Railway. 2 flights of internal stairs (may not be suitable for those with mobility issues) lead to self catering accommodation with open plan living space: kitchen, dining area & comfortable modern seating area. 1 twin bedroom. Shower room. Off-road parking for 1 car. Sorry no pets. Pickering shop & pub 3 minutes’ walk.
More info…….!

Station View ( Ref 951135 ) Pickering North Yorkshire    Station View ( Ref 951135 ) Pickering North Yorkshire holiday cottage sleeps 2    Station View ( Ref 951135 ) Pickering holiday apartment rental for 2 guests

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

Delightful period townhouse in central Pickering location facing market place & near to railway station – ideal for get-togethers! Property dates back to 1793 when the building was a Saddlers. Original features such as oak beams & inglenook fireplace have been retained. Accommodation is set over 3 floors. Ground floor has open plan kitchen/dining area with wood-burner & spacious lounge. 3 first floor bedrooms: 1 super king-size, 1 king-size, 1 double & family bathroom. 2 second floor bedrooms: 1 king-size & 1 double, both with additional single bed. Shower room. Toilet. Charming patio to rear with furniture & barbecue. Outdoor shed with fridge & dryer. Off-road car parking for 1 car, more parking within 2 minutes’ walk. Sorry no pets. Short walk to Pickering amenities.
More info…….!

Pickering holiday cottage for 11 guests in North Yorkshire    Pickering holiday cottage - North Yorkshire holiday cottage sleeps 11    Pickering holiday cottage rental for 11 guests

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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! Beck Cottage 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. Small sheltered 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…….!

Beck Cottage Pickering ( Ref 24339 ) Pickering self catering accommodation North Yorkshire    Beck Cottage ( Ref 24339 ) Pickering - North Yorkshire holiday cottage sleeps 6    Beck Cottage Pickering ( Ref 24339 ) Rent Pickering holiday cottage for 4 guests

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Photo of Dovecote Cottage ( Ref 1018399 ) Holiday cottage in Pickering Ryedale North Yorkshire - Self catering accommodationDovecote, Pickering – 1018399
Two bedrooms – Sleeps 4

Stone-built holiday cottage located a short stroll to Pickering attractions & amenities. Dovecote offers self catering accommodation for 4 guests. Stylish kitchen, dining room, utility, 1 beamed en-suite double bedroom & bathroom. 1 beamed king-size bedroom (zip & link – can be twin). Steep stairs to first floor beamed sitting room with sofa bed. Enclosed rear garden with furniture. Roadside car parking. 1 well-behaved pet welcome. Shop & pub within 0.1 miles. N.B. internal steps in property.
More info…….!

Dovecote Cottage ( Ref 1018399 ) Pickering North Yorkshire    Dovecote Cottage Pickering ( Ref 1018399 ) North Yorkshire holiday cottage sleeps 4    Dovecote Cottage ( Ref 1018399 ) Pickering holiday cottage rental

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Photo of Dove Cottage ( Ref 1033746 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireDove Cottage, Pickering – 1033746
Two bedrooms – Sleeps 4

Grade II listed three-storey holiday cottage for 4 guests, set in heart of Pickering – ideal for couples & small families! Dove Cottage offers self catering accommodation, renovated to high standard & retaining many period features. Ground floor has cosy sitting room with wood-burning stove in inglenook fireplace & stylish shaker-style kitchen with dining area. First floor has 1 boutique style bedroom with king-size bed, cast-iron fireplace & window seat. Bathroom. Second floor has 1 twin bedroom (zip & link – can be super king-size). Sheltered private courtyard with patio furniture. Utility room/secure storage for 4 cycles. Designated parking for 1 car in Black Swan pub car park. 1 well-behaved dog welcome (more on request). Shop & pub 0.1 miles.
More info…….!

Dove Cottage ( Ref 1033746 ) Pickering North Yorkshire    Dove Cottage ( Ref 1033746 ) Pickering North Yorkshire holiday cottage sleeps 4    Dove Cottage Pickering ( Ref 1033746 ) North Yorkshire Holiday cottage rental for 4 guests

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Photo of Adelaide's Cottage ( Ref 1111683 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireAdelaide’s Cottage, Pickering – 1111683
Two bedrooms – Sleeps 4

Centrally located holiday cottage in Pickering for 4 guests, short distance from amenities & attractions. Adelaide’s Cottage offers self catering accommodation with original beamed ceilings throughout. Ground floor has country-style well-equipped kitchen with dining area & inviting sitting room. 2 well-presented first floor bedrooms: 1 king-size & 1 twin. Contemporary shower room. Small shared seating area. Short walk to on-street car parking. 1 small well-behaved dog welcome (not left unattended). Shop & pub 0.1 miles.
More info…….!

Adelaide's Cottage ( Ref 1111683 ) Pickering North Yorkshire    Adelaide's Cottage ( Ref 1111683 ) Pickering North Yorkshire holiday cottage sleeps 4    Adelaide's Cottage Pickering ( Ref 1111683 ) North Yorkshire Holiday cottage rental for 4 guests

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Pickering Castle in North Yorkshire England

Visit Pickering Castle (English Heritage)

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Photo of 31 Outgang Road ( Ref 953578 ) Rent Pickering holiday cottage sleeps 2 - Ryedale self catering accommodation in North Yorkshire31 Outgang Road, Pickering – 953578
One bedroom – Sleeps 2

31 Outgang Road is a homely terraced Pickering holiday cottage – ideal for a couple! Property offers cosy self catering accommodation with characterful ceiling beams on ground floor. Well-equipped kitchen with breakfast bar & sitting room with wood-burner. 1 first floor double bedroom. Bathroom. Enclosed lawned garden to rear with patio & furniture. Roadside car parking. 1 well-behaved pet welcome. Pickering shops, pubs & restaurants 10 minutes’ walk.
More info…….!

31 Outgang Road ( Ref 953578 ) Pickering holiday home in North Yorkshire    31 Outgang Road Pickering ( Ref 953578 ) North Yorkshire holiday cottage sleeps 2    31 Outgang Road ( Ref 953578 ) Pickering North Yorkshire Holiday cottage rental

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Photo of Cobblers Cottage ( Ref 936135 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireCobbler’s Cottage, Pickering – 936135
Three bedrooms – Sleeps 5

Attractive stone-built semi-detached Grade II Listed holiday cottage in Pickering set on main A170 road. Cobbler’s Cottage has been refurbished to a high standard & is located 5 minutes’ walk from town centre amenities. Accommodation has well-equipped kitchen, dining room & cosy sitting room with wood-burner. Utility with bike/push chair storage. 3 bedrooms: 1 king-size double, 1 double & 1 single with pull-out stacker bed. Bathroom & toilet. Roadside car parking: first come, first served. 2 well-behaved dogs welcome. Shop & pub 2 minutes’ walk.
More info…….!

Cobblers Cottage ( Ref 936135 ) Pickering North Yorkshire    Cobblers Cottage Pickering ( Ref 936135 ) North Yorkshire holiday cottage sleeps 5    Cobblers Cottage ( Ref 936135 ) Pickering - North Yorkshire Holiday cottage rental

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Photo of Bay Tree Cottage ( Ref 1115722 ) Rent Pickering holiday cottage - Ryedale self catering accommodation in North YorkshireBay Tree Cottage, Pickering – 1115722
Two bedrooms – Sleeps 4

Beautifully-presented Pickering holiday cottage for 4 guests, located in Westgate on main A170 road. Bay Tree Cottage offers tastefully furnished welcoming property – ideal for a couple or family! Accommodation is set over 3 floors. Ground floor has light & airy beamed living/dining room with open stonework & wood-burning stove, amply-fitted kitchen & cloakroom. First floor has 1 double bedroom. Bathroom. Second floor has 1 twin bedroom. South-facing patio with furniture. Roadside car parking. Sorry no pets. Short walking distance to town amenities.
More info…….!

Bay Tree Cottage ( Ref 1115722 ) Pickering North Yorkshire    Bay Tree Cottage Pickering ( Ref 1115722 ) North Yorkshire holiday cottage sleeps 4    Bay Tree Cottage ( Ref 1115722 ) Pickering holiday cottage rental

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

Attractive semi-detached holiday cottage, which adjoins the owners’ home & bed/breakfast, set back from the main A170 road. Westgate Cottage is 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 bike storage. Off-road parking for 1 car. Sorry no pets. Shop 5 minutes’ walk & pub 2 minutes’ walk. Good base for exploring North York Moors & eastern coastal resorts.
More info…….!

Westgate Cottage ( Ref 904479 ) Pickering North Yorkshire    Westgate Cottage Pickering ( Ref 904479 ) North Yorkshire holiday cottage sleeps 4    Westgate Cottage ( Ref 904479 ) - Pickering holiday cottage rental

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Photo of Lockton Cottage ( Ref 983666 ) Pickering holiday cottage - Self catering accommodation in Ryedale North YorkshireLockton Cottage, Pickering – 983666
Two bedrooms – Sleeps 4

Grade II Listed end terrace stone-built holiday cottage in Pickering. Lockton Cottage offers an ideal base for exploring the area – suitable for families or friends! Ground floor accommodation 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. Lockton Cottage is on main A170 road but is secondary glazed.
More info…….!

Lockton Cottage ( Ref 983666 ) Pickering North Yorkshire    Lockton Cottage Pickering ( Ref 983666 ) North Yorkshire holiday cottage sleeps 4    Lockton Cottage Pickering ( Ref 983666 ) - Pickering holiday cottage rental for 4 guests

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Photo of Duckys ( Ref 1102719 ) Pickering holiday cottage for 4 guests - Self catering accommodation in Ryedale North YorkshireDucky’s, Pickering – 1102719
Three bedrooms – Sleeps maximum 4

Superb terraced Pickering holiday cottage for 4 guests. Ducky’s offers pet-friendly self catering accommodation – ideal for couples or a family! Ground floor has spacious well-equipped kitchen with dining area & sitting room with wood-burning stove. 3 well-presented bedrooms on first floor: 1 king-size & 2 singles. Bathroom. Rear garden with lawn & furniture. Bike store. Off-road parking for 3 cars. 2 well-behaved pets welcome. Sorry no stag/hen parties or single gender groups under the age of 25. Shop 0.5 miles & pub 0.2 miles.
More info…….!

Duckys ( Ref 1102719 ) Holiday cottage in Pickering North Yorkshire    Duckys ( Ref 1102719 ) Pickering North Yorkshire holiday cottage sleeps 4    Duckys Pickering ( Ref 1102719 ) North Yorkshire Holiday cottage rental

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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

The Old Cartway is a charming mid-terrace stone-built holiday cottage on main A170 road 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 of property. 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…….!

The Old Cartway Pickering ( Ref 964829 ) Holiday cottage in Pickering North Yorkshire    The Old Cartway Pickering ( Ref 964829 ) North Yorkshire holiday cottage sleeps 6    The Old Cartway ( Ref 964829 ) Pickering holiday cottage rental for 6 guests

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Photo of 17 Costa Way ( Ref 1070204 ) Rent Pickering holiday home sleeps 5 - Ryedale self catering accommodation in North Yorkshire17 Costa Way, Pickering – 1070204
Three bedrooms – Sleeps 5

Inviting holiday bungalow for 5 guests, set in residential area on outskirts of Pickering. 17 Costa Way offers lovingly furnished ground floor accommodation – ideal for family & friends! Living/dining room with electric fire. Kitchen. 3 bedrooms: 1 en-suite double, 1 double & 1 single. Bathroom. Enclosed garden with lawn & summerhouse. Off-road parking for 1 car, additional roadside parking available. 1 well-behaved pet welcome. Shop & pub 0.5 miles.
More info…….!

17 Costa Way ( Ref 1070204 ) Pickering North Yorkshire    17 Costa Way Pickering ( Ref 1070204 ) North Yorkshire holiday cottage sleeps 3    17 Costa Way ( Ref 1070204 ) Pickering - North Yorkshire Holiday cottage rental

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

Enjoy a trip on the popular North Yorkshire Moors Railway

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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 Pickering holiday cottage oozes charm & character. Property is set on Castlegate leading to Pickering Castle. Keep Cottage is stylishly appointed throughout. Ground floor accommodation has a well-equipped kitchen with dining area set in brick alcove & welcoming 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 car parking outside Keep Cottage. 1 well-behaved dog welcome. Pickering shop & pub 5 minutes’ walk. N.B. low beams in property.
More info…….!

Keep Cottage ( Ref 904784 ) Rent Pickering holiday home in North Yorkshire    Keep Cottage Pickering ( Ref 904784 ) North Yorkshire holiday cottage sleeps 5    Keep Cottage ( Ref 904784 ) Pickering - North Yorkshire Holiday cottage rental

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Photo of 12 Castlegate ( Ref 1119779 ) Pickering holiday cottage for 4 guests - Ryedale self catering accommodation in North Yorkshire12 Castlegate, Pickering – 1119779
Two bedrooms – Sleeps 3-4

Attractive characterful terraced Grade II Listed holiday cottage near Pickering Castle. 12 Castlegate offers tastefully furnished & decorated accommodation for 4 guests. Ground floor has beamed sitting room with open fire, separate dining room, sleek kitchen & bathroom. 2 first floor bedrooms: 1 double & 1 single with pull-out bed. Private enclosed garden with furniture & barbecue. Roadside car parking: first come, first served. 1 well-behaved dog welcome (downstairs only). Shop 0.3 miles & pub 0.4 miles. N.B. 2 steps down to kitchen.
More info…….!

12 Castlegate Pickering ( Ref 1119779 ) Rent Pickering holiday home in North Yorkshire    12 Castlegate Pickering ( Ref 1119779 ) North Yorkshire holiday cottage sleeps 4    12 Castlegate Pickering ( Ref 1119779 ) - North Yorkshire Holiday cottage rental

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Photo of Robin Cottage ( Ref 1119942 ) Pickering holiday cottage North YorkshireRobin Cottage, Pickering – 1119942
Two bedrooms – Sleeps 4

Delightful two-bedroom Pickering holiday cottage for 4 guests. Robin Cottage is set close to local amenities & attractions – ideal base for couples or a family wishing to explore the area! Ground floor has hallway, inviting living/dining room with ‘flame-effect’ electric fire & well-equipped kitchen. 2 first floor bedrooms: 1 super king-size (zip & link – can be twin) & 1 king-size. Shower room. Rear garden with lawn, furniture & summerhouse. Roadside car parking: first come, first served (can unload outside property). Sorry no pets. Shop 0.2 miles & pub 0.1 miles.
More info…….!

Robin Cottage ( Ref 1119942 ) Rent Pickering holiday home in North Yorkshire    Robin Cottage Pickering ( Ref 1119942 ) North Yorkshire holiday home sleeps 4    Robin Cottage ( Ref 1119942 ) Pickering - North Yorkshire Holiday cottage rental

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View more Pickering Holiday Cottages – Page 2

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Enjoy your holiday cottage in Pickering, North Yorkshire!

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View other holiday cottages in Cropton – Wrelton – Sinnington – Rosedale – Hutton le Hole – Kirkbymoorside – Harome – Helmsley – Hovingham – Newton Upon Rawcliffe – Thornton-le-Dale – Lockton & Levisham – Wilton – Goathland – Castleton – Danby – Glaisdale – Staithes – Whitby 1 – Whitby 2 – Whitby area – Robin Hood’s Bay – Scarborough – Scarborough area – Staxton & Ganton – Filey – Little Barugh & Marishes – Malton area – York – York Apartments – York area