Dog-Friendly Cottages in Pickering

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Your Pickering, North Yorkshire search returned 128 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A stone, terraced cottage resting in market town of Pickering, North Yorkshire. Open fire. WiFi. Excellent area for walking, cycling and touring. Close to coast. Kirkbymoorside 7 miles. (Ref. 1119779)

  • Wi-fi
  • Dishwasher
  • 15% off - Fri 8th Aug to 31st Aug 2025

7 nights from £360

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8

    Sykes Rating

An attractive, mid-terrace barn conversion resting in Marton near Kirkbymoorside, North Yorkshire. Woodburning stove. Pet-friendly. Enclosed garden. Off-road parking. Pickering 4.8 miles; Helmsley 9.1 miles. (Ref. 1081033)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £379

Last booked 5 hours ago
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  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0

    Sykes Rating

This inviting mid-terrace sits at the centre of Pickering in North Yorkshire, on the fringes of the North York Moors National Park. Three-storey. Pet-friendly. Amenities in walking distance. Malton 8.7 miles; Scarborough 18.2 miles; York 26.8 miles. (Ref. 1025071)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £377

Last booked yesterday
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7 nights from £394

  • Sleeps8
  • Bedrooms4
  • PetsYes

    5.0

    Sykes Rating

This delightful detached house is situated in Sinnington, North Yorkshire. WiFi, Pet-friendly, Off-road parking. Pickering 3 miles; Kirkbymoorside 3.5 miles. (Ref. 998951)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £619

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A wonderful stone bungalow located in the village of Gillamoor, North Yorkshire. Open-plan. Woodburner. Open countryside views. Kirkbymoorside 2.7 miles; Pickering 11 miles. (Ref. 984261)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Games room

7 nights from £476

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Beth's Cottage, a splendid holiday cottage resting just outside Sherburn, North Yorkshire. Open-plan living space. Single-storey. Enclosed garden. Filey 15.2 miles; Scarborough 15.4 miles; York 25.6 miles. (Ref. 1148578)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £662

  • Sleeps5
  • Bedrooms3
  • PetsYes

    4.9

    Sykes Rating

A wood-clad lodge resting within the town of Kirkbymoorside. All-ground-floor. Pet-friendly. WiFi. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011653)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £479

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

A stunning two bedroom lodge nestled in Allerston, North Yorkshire. Hot tub. Woodburning stove.Off-road parking. Rural. Pickering 5.2 miles; Scarborough 16.2 miles; Helmsley 17.8 miles. (Ref. 1097488)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Baby-friendly

7 nights from £885

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

Delightful detached stone cottage on owner's complex in Appleton-le-Moors village. Cosy, characterful accommodation with open fire, garden room, fine views over open countryside. Wonderful walking/cycling from the door. Kirkbymoorside 3.5 miles. (Ref. 936454)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £448

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Low Grounds Cottage, a wonderful holiday bungalow resting just outside Harome, North Yorkshire. Woodburning stove. Rural location. Private driveway. Kirkbymoorside 6 miles; Pickering 13.1 miles; Thirsk 17.7 miles; York 23.7 miles. (Ref. 1153174)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £490

  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A stunning, two-bedroom lodge resting in Allerston near Thornton Dale, North Yorkshire. Hot tub. Woodburning stove. Open-plan. Pickering 5.2 miles; Scarborough 16.2 miles; Helmsley 17.8 miles. (Ref. 1097485)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher

7 nights from £869

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This quaint, single-storey barn conversion rests in Scagglethorpe, North Yorkshire. Pet-friendly. Off-road parking. Woodburning stove. Garden with furniture. Malton 4.3 miles; Scarborough 18.9 miles; York 22.5 miles. (Ref. 981428)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £317

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Molly's Cottage, a beautifully-decorated holiday abode in the lovely village of East Knapton near Rillington, North Yorkshire. Underfloor heating. Off-road parking. Pet-friendly. Filey 15.2 miles; Scarborough 15.4 miles; York 25.6 miles. (Ref. 1148579)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £590

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Nell's Cottage is a wonderful, single-storey cottage nestled in rural East Knapton, near Rillington, North Yorkshire. Pet-friendly. Open-plan. Romantic. Malton 8 miles; North York Moors National Park 13.2 miles; York 25.6 miles; Scarborough 15.4 miles. (Ref. 1148580)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £491

  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This romantic detached bungalow resides on the outskirts of Pickering, North Yorkshire. WiFi. Remote. Garden. Woodburning stove. Kirkbymoorside 7.5 miles; Helmsley 13 miles; Scarborough 18.5 miles. (Ref. 1062267)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine

7 nights from £372

  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0

    Sykes Rating

A superb, detached lodge resting on the outskirts of Kirkbymoorside. All-ground-floor. WiFi. Pet-friendly. Pickering 7.8 miles; Scarborough 25.4 miles. (Ref. 1011649)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Baby-friendly

7 nights from £523

Last booked 2 days ago
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

Millers Cottage is a detached bungalow resting in the hamlet of Old Malton, near Malton, North Yorkshire. Close to a shop and pub. Couple’s retreat. Malton 1 mile; Pickering 7.4 miles; North York Moors National Park 9.4 miles. (Ref. 1147474)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £377

  • Sleeps3
  • Bedrooms2
  • PetsYes

    4.9

    Sykes Rating

A charming two-bedroom cottage resting near Brompton-By-Sawdon, Scarborough. Woodburning stove. Close to amenities. Pet-friendly. Beautiful views. Scarborough 9.8 miles; Pickering 9.9 miles; York 32.3 miles. (Ref. 1108141)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine

7 nights from £389

  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

Grade II listed mid-terrace cottage resting in Pickering town centre. Woodburning stove. Pet-friendly. Kirkbymoorside 7.2 miles; Scarborough 17.9 miles. (Ref. 1033746)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £495

Stay in the heart of North Yorkshire with your pooch by booking to stay at one of these dog-friendly cottages in Pickering for your next staycation! 

Why Book Dog-Friendly Cottages in Pickering? 

If bringing your four-legged friends along on holiday with you is a must-do, then you’ve come to the right place with this collection of dog-friendly cottages in Pickering. 

Nestled in the middle of North Yorkshire’s wide-open countryside, these properties are also no more than a short drive away from the North York Moors and the beautiful Yorkshire Coast, giving you the chance to enjoy the best of both worlds. 

The properties themselves also come complete with dog-friendly furnishings, lots of space to unwind and relax and all the amenities and creature comforts that you’re used to at home. You can also enjoy wonderful walks with your pooch along Pickering Beck or around the ruins of Pickering Castles; there's so much to explore with your pooch by your side.

So, whether you plan on spending your time wandering across the countryside, relaxing at one of the region’s best beaches or exploring historic sites and monuments, you can do it all from these pet-friendly cottages in Pickering! 

Explore plenty of other ideas on what to see and do here with our North Yorkshire Travel Guide » 

Places to Visit from these Pickering Dog-Friendly Cottages 

With so much to see, do and explore from these dog-friendly cottages in Pickering, you’ll have no issues planning your day trips and adventures whilst staying here on your next break! 

For those of you that want to spend time by the coast should head to the bustling seaside town of Scarborough. Found on the Yorkshire Coast and only a 35-minute drive from these properties, it's a place that’s long been a popular holiday hotspot in the region. 

Whilst visiting, be sure to head down to the town’s beautiful South Bay Beach for a walk along the sands with your pooch before stopping off somewhere for a delicious fish and chips, a delicacy that makes this region world-famous. If you have the time, we’d also recommend taking a walk up to the historic Scarborough Castle to take in the stunning views of the town and out across the North Sea. 

Another great place to consider visiting from these pet-friendly cottages in Pickering is the bustling market town of Malton. Situated just a 15-minute drive away, it’s often regarded as the “Food Capital of North Yorkshire” due to the vast amount of well-renowned restaurants that can be found all over the town centre. Not only that, but it’s also nestled right on the edge of the Howardian Hills, an impressive area of natural beauty that once made up the majority of the Castle Howard estate and a great place to explore with your dog. 

Other Popular Destinations near these Pet-Friendly Cottages in Pickering: 

Bridlington 

Filey 

Hunmanby 

Robin Hood’s Bay 

Whitby 

Types of Pickering Holidays 

Aside from these dog-friendly cottages in Pickering, there’s also a full collection of all available holiday cottages in Pickering to take a look at, as well as a larger collection of dog-friendly cottages in North Yorkshire. You can also choose from these lodges in Pickering