Dog Friendly Cottages in Pickering: 12 Luxury Holiday Lets

Handpicked Cottages to Rent

Finding the best dog friendly cottages in Pickering aren’t hard to find. Between the four major towns of Scarborough, Whitby, Helmsley, and Malton is the southern terminus of the North Yorkshire Moors Railway. Pickering, known as the gateway to the North York Moors National Park, is a civil parish resting within an area of old stone cottages, a picturesque location that is a trendy choice for people with pooches. 


We search the best dog friendly cottages in Pickering, so you don't have to!

featured image for dog friendly holiday cottages in Pickering
Normanby, Near Pickering

Enjoy soaking in your own private hot tub or warming up beside the quaint fireplace; this picturesque Pickering cottage is a lovely romantic getaway for couples looking to unwind in the North Yorkshire countryside and take in its breathtaking natural beauty.

Thornton le Dale, Near Pickering

A lovingly restored barn, directly on the edge of the Yorkshire Moors, this beautiful property is situated on a working farm with spectacular views of fields and forests stretching as far as the eye can see. Enjoy the scenic village of Allerston, just a short drive away.

Thornton Dale, Near Pickering

This gorgeous ex-granary building has been lovingly renovated to include stunning floor to ceiling windows and an open and spacious living area. Sat on the edge of the North Yorkshire Moors, there are many beautiful countryside walks in Pickering to be enjoyed right from the door.

Normanby, Near Pickering

A charming and characterful cottage with its own private hot tub, this welcoming property is perfect for groups of up to 5 to enjoy the beautiful village of Normanby. With the Yorkshire Dales and local coastline just a short drive away, there’s no end of natural beauty to explore.

Scarborough, Near Pickering

This stunning detached property is bright and spacious, with loads of room for a family of 4 to sprawl out and relax. Enjoy soaking in the hot tub after a long day of exploring the local area, with sandy beaches and rugged coastlines just a short drive away.


A bright and inviting property with a cosy fireplace and spacious living area, this lovely retreat is ideally situated for trips to both the Yorkshire coast and the Yorkshire Moors. Take a short stroll to the historic market town of Pickering, and sample its idyllic shops and eateries.


This spacious holiday chalet backs onto a lush forest, with its own private woodland walk for perfect immersion into the natural beauty of North Yorkshire. Enjoy relaxing on the gorgeous decking, or take a short wander into the quaint village of Pickering to explore the local area.

Thornton le Dale, Near Pickering

A traditional Pickering corner cottage on the edge of the North Yorkshire Moors National Park, this cosy home features a lovely enclosed garden and patio and a roaring fireplace, perfect for warming up after exploring the natural beauty of the Moors.

Pickering, North York Moors

This superb cottage is ideal for a large group wanting a seaside stay. There are four bedrooms and two bathrooms, whilst outside parking for 4 cars, a garage for storage and a summer house in the lawned garden. Helmsley is just 13 miles, whilst the fantastic city of York is 27 miles. 

Pickering, North York Moors

A brilliant family holiday home, this semi detached cottage has three bedrooms and one family bathroom. A travel cot and highchair are available if you have young children, whilst there’s an enclosed garden with a picnic table and private parking for two vehicles. The North York Moors are on your doorstep and you’re less than a mile from Pickering Castle.

Pickering, North York Moors

This cosy Victorian cottage is perfect for a small family needing to escape to the countryside. It has a double and a twin bedroom, as well as a shower room and a utility room. Facilities include bike storage, a games room with a snooker table, and dog bowls. Jump on the North Yorkshire Moor’s Railway, which takes you from Pickering into Grosmont.

Pickering, North York Moors

A delightful converted barn ideal for a romantic retreat. It has one king size bedroom and one bathroom, outside there’s a large patio area with table and chairs and inside there’s a smart TV, Alexa and a welcome pack on arrival. Pickering Castle is just two and a half miles away, or you can head to the National Park, which is four miles and has a variety of walking routes and cycling trails.

Contact Us

List Your Pet Property Today

The Best Pet Friendly Holiday Cottages in Pickering

To ensure you and Fido find the perfect beautiful North York Moors holiday, we have listed our top picks of holiday cottages in Pickering for dogs.

Whether it is walking on the North York Moors, round Pickering market town, mountain biking in the natural beauty, sitting back and watching the world go by on a steam train or, having tea in the market town’s Middleton Post Office Tea Parlour, you are going to be in for a treat. You can’t visit North Yorkshire without sampling a pint from Black Sheep Brewery or the North Yorkshire Brewery.

A short drive from Pickering to the stunning coastline where Robin Hoods Bay and Whitby await this beautiful location of farms cluster is one of the largest cottage providers to rival even the likes of the Lake District. 

About Holidays In Pickering With Dogs

This destination is no ordinary market town deep in Pickering countryside; its natural beauty, local market towns, traditional shops, tea rooms, local village greens, nearby coastal attractions and, idyllic setting make it the perfect location for some of our favourite properties for you and your pooch… Pickering is a popular market town, a peaceful haven (except for extremely busy market days) full of surprises for your family and Fido included. Not only is Pickering a traditional trainspotter’s heaven, its drawcard includes the Dalby Forest, host of world championship mountain biking, just half an hour’s drive away.

North Yorkshire has a small market town or picturesque village on every turn, most having withstood modernity ravages, and Pickering is up there with the best. The dog friendly accommodation in Pickering plays tribute to this preservation of days gone by with almost all of the cottages made of North Yorkshire stone and retaining most of their original features.

In keeping with the historic feel, with the North Yorkshire Moors Railway Station in its midst, this market town has more than 100 traditional shops and independent outlets. It maintains that magical balance of old and new in its different quarters, joined by cobbled streets and rises. It has a traditional market every Monday too and a monthly farmers’ market. Nearby Thornton le Dale is well worth a visit too.

Just 10 miles north-east of Pickering is a gem in the North Yorkshire Crown – Dalby Forest that is great for walks, mountain bike trails for the whole family and even a summer music festival, Forest Live, organised by the Forestry Commission of North Yorkshire.

For a right royal day out with Rover, a visit to Pickering Castle has to be on your list. This splendid North Yorkshire edifice has fabulous views over the North York Moors National Park. Rising above the market town, it is a great spot for hounds that like hill climbing.  

Flamingo Land

Fido need not fret because he won’t be left out of this family day out. Dogs are allowed in Flamingo Land, a theme park and zoo, just outside Pickering. With seven themed areas and an active play zone for the younger set, you are going to need a full day to enjoy it all.

Visit the Lost Kingdom’s plains, where lions and other predators roam and let the kids enjoy the wacky world of Splosh. There are eight extreme rides for thrill-seekers, including the Mumbo Jumbo, the world’s steepest drop. Find dog friendly places to stay in Pickering dotted around many of these attractions.

Beck Isle Museum, North Yorkshire

For an insight into Pickering’s fascinating history and local life through the ages, visit the Beck Isle Museum housed in a stately building beside the beck. Recreations of period shops filled with produce from days of yore are accurate to the T.

Paws are not permitted inside but take it in turns to be the designated canine chaperone because pooches are permitted in the pretty courtyard. Take a walk along the beck and feed the ducks until it’s your turn to experience the delights of this independent museum.

Steam Train it to the Coast across the York Moors National Park.

Many Pickering dog friendly cottages in the portfolio are opposite the North Yorkshire Moors Railway Station, where you can board a steam train for a trip to Whitby. You will travel through parts of the breathtaking North York, marvelling at the breathtaking scenery before arriving at the iconic seaside town.

There are several stations where you and your dogs can disembark, the most popular being Goathland, otherwise known as the “Harry Potter stop” because it was used in the first film as Hogsmede Station.

Last Word

If you are looking for Yorkshire holiday ideas, a week away with the North York Moors on your doorstep means plenty of days out with your dogs. And it’s okay too if you want to chill in your cottage’s courtyard or garden, having sundowners, a BBQ or, your cup of morning coffee.

Beautiful Pickering countryside beckons with pet friendly cottages in Pickering and it is best to make your base in the very gateway to the North York Moors, whether it’s a picture-perfect cottage or a barn with a wood burner and private parking.

Take a look at all the pet friendly Yorkshire cottages currently available to rent.

This website uses cookies to ensure you get the best experience on our website.