Pet-friendly vacation rentals in Pickering

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Top-rated pet-friendly home rentals in Pickering

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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The kitchen area is designed with a wood countertop and light cabinetry. A sink is located beside a window that allows natural light to illuminate the space. Fresh greenery is positioned on the sill, and neatly arranged utensils and containers enhance the organized ambiance.
Cottage in North Yorkshire
4.82 out of 5 average rating, 287 reviews

Cosy ‘Cobblers Cottage’ - Pickering

Enjoy easy access to everything from our perfectly located, traditional stone home on the gateway to the North York Moors National Park. Just steps away from Pickering town centre with an array of shops, pubs, cafes, bars, restaurants, bakers, butchers & takeaways on offer. A short stroll to the North Yorkshire Moors Railway giving pleasant & easy access to Whitby, Goathland, Levisham, Newtondale and Grosmont. Also perfectly located for Scarborough, Whitby, Malton, Helmsley & Dalby Forrest.

Top guest favorite
A spacious living area is presented with a blend of rustic and modern decor. A wood-burning stove is situated next to a large window, illuminating a comfortable sofa and dining table. A vibrant area rug adds color, while large light fixtures create an inviting ambiance.
Barn in North Yorkshire
5 out of 5 average rating, 196 reviews

Blacksmith’s Barn - Cosy, Chilled & Dog Friendly.

Our beautifully converted barn is ideally located in the picturesque village of Ruston. Set within a stunning Grade II listed farmstead, just 50 metres from the edge of the North York Moors National Park & with easy access of coastal walks, beaches & market towns including Whitby, Pickering, Filey, Cayton & Malton. Stylishly & comfortably furnished, the ground floor is roomy & open plan with a wood burner & under floor heating. The mezzanine bedroom has a super comfortable King size bed & bath.

Top guest favorite
The cottage is constructed of traditional stone, showcasing a quaint exterior with a pitched roof and chimney. Two large windows with flower boxes frame the entrance, which features a light-colored door. The surroundings include a peaceful street lined with other characterful buildings.
Cottage in North Yorkshire
4.92 out of 5 average rating, 335 reviews

Cosy character cottage in heart of Pickering

31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Top guest favorite
A charming Victorian stone cottage stands against a backdrop of greenery. The cottage features a mix of dark stone and light brick, with a small front porch and a sloped garden area. Two large windows allow natural light to enter the welcoming interior.
Home in North Yorkshire
4.97 out of 5 average rating, 110 reviews

Stationmaster's Cottage

A detached Victorian stone cottage in the shadow of Pickering Castle and overlooking North York Moors Railway station, this characterful property with real fire is only 3 minutes walk away from town centre amenities, the castle and a ten minute walk to the start of the Tabular Hills way and gateway to the North York Moors National Park. Free parking is provided in the Platform 3 Car Park diagonally opposite the property 70 yards away (dashboard pass provided). Please note: steep stepped access.

Top guest favorite
The exterior of a characterful Yorkshire longhouse is displayed, showcasing stone walls and a tiled roof. Flower baskets hang from the front, adding a touch of color. The entrance features a light-colored door framed by two potted plants. Windows reflect a welcoming ambiance.
Cottage in North Yorkshire
4.96 out of 5 average rating, 124 reviews

Spacious character historic cottage

Our 17th Century, characterful Yorkshire longhouse provides a spacious, retreat, and a fantastic base for family and friends to meet up with plenty of opportunities for days out in the surrounding North York Moors. The house is in the vibrant market town of Pickering with it's famous heritage railway. Pickering has a cafes, restaurants and pubs along it's bustling high street and a weekly market selling fresh, local produce. 7+2 guests (sofa bed in the snug for 2 guests at an extra charge)

Top guest favorite
Fields and rolling hills stretch into the distance under a clear sky, with scattered clouds casting soft shadows on the landscape. A wooden gate opens into the lush, green path leading towards open meadows, inviting exploration in the tranquil countryside.
Cottage in North York Moors National Park
4.99 out of 5 average rating, 589 reviews

Fully Fenced Dog Field, Sea Views & Forest Walks

Enjoy your morning coffee in the warmth of Woodpeckers Cottage, Silpho as you watch the winter sun rise over the sea. Enjoy time with your dog in the fully fenced field, as the warm morning mist rises from the dewy grass. Take in the far-reaching views and watch deer graze in nearby fields. Take the scenic drive to dog-friendly beaches for refreshing winter walks in the salty air. At the end of the day, wrap up in a snuggle blanket, sit outside, and gaze at the stars in this Dark Sky Reserve.

Guest favorite
The exterior of a charming stone cottage is visible, featuring a traditional roof with red tiles. Two entrances can be seen, framed by multiple windows that allow natural light to enter. The facade combines a rustic aesthetic with neighborhood characteristics.
Cottage in North Yorkshire
4.94 out of 5 average rating, 139 reviews

Lovely cottage for N. York Moors & Steam Trains

19 Burgate is in the popular market town of Pickering, minutes’ walk from shops, eating places, Castle & Steam Railway (seasonal) - ideal for exploring the Moors, coastline & historic sights. It offers contemporary comfort, with a cosy living room, modern kitchen-diner, luxurious bathroom (walk-in shower, bath) & quality bedrooms. The garden offers eating/drinks outside and access to private parking. Prices are for 2 guests, with a small extra charge for the 2nd bedroom and well-behaved pets.

Guest favorite
A hot tub is positioned on a paved area, surrounded by gravel and wooden fencing. Lush greenery is visible in the background, with a cloud of steam rising from a passing steam locomotive, creating a unique view. Outdoor seating can be seen nearby.
Cottage in Newbridge
4.91 out of 5 average rating, 175 reviews

3 Railway Cottage Pickering , Hot Tub, Pets all'd

3 Railway Cottages is a cosy well equipped self-catering cottage, located just one mile from the market town of Pickering. It is dog friendly (£10 per dog per night) with a hot tub and garden including outdoor seating and a train viewing area right bedside the NYMR heritage railway. The cottage lies at the foot of the North York Moors and has many footpaths and bridleways close by for walkers and cyclists. The cottage sleeps up to 4 adults and has everything you need for a comfortable stay

Top guest favorite
The living kitchen area features exposed beams and floral wallpaper. A cozy seating arrangement is complemented by a plush rug and a vintage cast iron stove. Kitchen amenities are visible, including a stove, oven, and storage. Warm light fixtures illuminate the space.
Guest suite in Rosedale Abbey
4.99 out of 5 average rating, 244 reviews

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Top guest favorite
A scenic view of a cottage by the River Seven is presented, with a backdrop of lush greenery and blooming daffodils adorning the riverbank. The charming stone building features a red-tiled roof and multiple windows reflecting the serene countryside.
Cottage in Sinnington
4.98 out of 5 average rating, 132 reviews

Goose End Cottage, North Yorkshire

Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

Top guest favorite
The exterior of the Annex features a stone facade with a rustic tiled roof. A light-colored door is placed centrally, flanked by small windows. Lush green plants and flowers are positioned at the entrance, enhancing the welcoming appearance amidst a garden setting.
Tiny home in Urra
4.98 out of 5 average rating, 166 reviews

Maltkiln House Annexe North Yorkshire moors

Maltkiln House Annex is the perfect getaway for two people who love to be in the countryside. You can enjoy uninterrupted views sitting at the bottom of the garden which is your own space. The Annex dates back to the 16th century and is full of charm. You can walk from our Annex straight up onto the Cleveland way where you can walk or bike for miles. Our Annex is a popular stop off for people walking the coast to coast. We are also very close to some great pubs and restaurants.

Top guest favorite
The living area features a cozy sofa covered with a soft grey throw, complemented by patterned cushions. A wooden dining table is visible nearby. Stone walls and exposed wooden beams create a charming, rustic feel, while a wood-burning stove adds warmth to the space.
Barn in North Yorkshire
4.92 out of 5 average rating, 291 reviews

Delightful Barn with log burner near Pickering

A tranquil, 19th century converted barn with private garden and outdoor fire overlooking the local countryside. A short drive from Pickering and close to the Moors, Whitby and York, the barn is great for a relaxing break. Inside, you will find a renovated living area, with a wood burning stove, Smart TV and fully fitted kitchen complete with oven, fridge washing machine and dish washer, the barn offers everything you will need for a relaxing getaway in Yorkshire.

Popular amenities for Pickering pet-friendly home rentals

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,448 GYDG$28,989 GYDG$29,614 GYDG$33,994 GYDG$33,994 GYDG$36,079 GYDG$37,748 GYDG$35,662 GYDG$35,871 GYDG$32,742 GYDG$30,448 GYDG$32,742 GYD
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Quick stats about vacation rentals that are pet-friendly in Pickering

  • Total vacation rentals

    Explore 80 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at G$14,599 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,430 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Pickering vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pickering rentals

  • 4.8 Average rating

    Pickering stays are highly rated by guests—averaging 4.8 out of 5!