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Family-friendly vacation rentals in Pickering

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Quick stats about vacation rentals that are family-friendly in Pickering

  • Total vacation rentals

    Explore 130 vacation rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at G$12,552 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Pickering vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pickering rentals

  • 4.9 Average rating

    Pickering stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Pickering

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

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Guest favorite
Cottage in North Yorkshire

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.

Indoor spacesKitchenBeach

4.82 out of 5 average rating, 345 reviews
Superhost
Home in North Yorkshire

Country Cottage with Steam Railway Views.

Positioned on a pedestrian road, wake up to the sound of birds or the steam railway. Cosy up to the log burner or sit out in the evening sun, on our west facing decking overlooking the railway. 1 minute walk to forest paths and Pickering castle, or a 2 minute walk to the town centre; you couldn’t be more perfectly located. Pickering has the charm of a rural North Yorkshire town with all the amenities you need for a relaxing break or a family centred vacation. Discounts for stays over 2 nights.

Indoor spacesFamilyLong stay

4.88 out of 5 average rating, 162 reviews
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

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.

Indoor spacesKitchenCleanliness

4.97 out of 5 average rating, 148 reviews
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

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.

Indoor spacesFamilyCheck-in

4.91 out of 5 average rating, 387 reviews
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

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)

Indoor spacesFamilySleep quality

4.95 out of 5 average rating, 139 reviews
Top 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

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.

FamilyIndoor spacesCheck-in

4.94 out of 5 average rating, 163 reviews
Top guest favorite
Cottage in North Yorkshire

Katiann's Cottage

Accommodation Master Bedroom, en-suite walk in shower, 1 x King Size Bed, Freeview TV Twin Bedroom - 2 single beds TV Travel cot & highchair available Bedlinen & Towels Bathroom - bath, shower, sink, toilet Kitchen Diner - dishwasher, Washer, electric oven & hob, fridge, microwave, cook utensils & iron Cosy lounge 2 leather recliner sofas, Smart TV, electric log burner Gas Central Heating Free Wi-fi 1 private parking space & plenty of free public parking & chargers nearby 1 x small dog fee

KitchenFamilyLaundry

4.98 out of 5 average rating, 188 reviews
Superhost
An outdoor courtyard is presented with a hot tub, framed by greenery and stone walls. A wooden table holding a teapot and cups adds a cozy touch. Decorative elements like pinecones and flowers enhance the space, inviting relaxation in this private setting.
Cottage in North Yorkshire

La Fenetre Holiday Cottage

Central location just one minute walk from the town centre with lots of shops, bars & restaurants. HOT TUB! Pet Friendly. Contact us for special offers. Private outdoor courtyard. Our cottage offers very comfortable accommodation and is within easy walking distance of amenities, parking very close by, the perfect base for exploring local attractions, including York, Whitby, Scarborough, Dalby Forest, Flamingo Land & North Yorkshire Moors. The cottage is snug & makes maximum use of space.

KitchenIndoor spacesLaundry

4.81 out of 5 average rating, 534 reviews
Top guest favorite
The exterior of the cottage displays a charming stone facade with a red-tiled roof. A large window with multiple panes is positioned at the front, while two dormer windows are set into the roof, providing additional natural light to the upper levels.
Cottage in North Yorkshire

Castlegate Cottage

Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.

FamilyIndoor spacesComfort

4.93 out of 5 average rating, 417 reviews
Top guest favorite
The open plan living area features a log burner surrounded by a brick fireplace, complemented by a comfortable blue chair and a coffee table. A dining area with a wooden table is visible in the background, while a fully equipped kitchen is accessed through an archway.
Cottage in North Yorkshire

2 bed Cottage Pickering, Priv Parking, Logburner

Oak Cottage is in the perfect place to explore Pickering and the surrounding North Yorkshire Moors and Coast. With Parking for 1 car and Just a 5 to 10 minute walk into central Pickering and the NYM Railway. Fully equipped for a comfortable and relaxing stay with lots of luxurious extras. We can sleep upto 4 people and one well behaved dog is welcome, but must be added to your booking for a small charge. It is a terraced cottage on the main road.

FamilyIndoor spacesQuiet

4.95 out of 5 average rating, 128 reviews
Guest favorite
A large floor-to-ceiling window offers expansive views of the countryside and sunlight filtering through trees. A warm wooden bench is adorned with a welcoming sign and small plants. A cozy coffee table with decorative items can be seen in front, enhancing the inviting space.
Barn in Aislaby

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion. It sits on the edge of the North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of Pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock and woodland. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom, pizza oven on site, parking, walkable pub.

KitchenIndoor spacesOutdoor spaces

4.94 out of 5 average rating, 382 reviews
Top guest favorite
The exterior of the cottage features a charming red-brick facade with a combination of rectangular and arched windows. The front door is painted in a soft blue, providing a welcoming contrast to the brickwork. The building's roof displays traditional tiles and a classic design.
Cottage in Thornton Dale

Lovely Cottage & Garden. Family & Bike Friendly

A stunning 3 bedroom cottage & garden in Thornton. Family & MTB/cyclist friendly. A converted period building in the beautiful North York Moors National Park, ideal as a base for your outdoor activities or quiet getaway in this famously picturesque Yorkshire village. Beautifully light and spacious stone cottage with period features and all modern facilities. Set in the quiet Prospect Place cul-de-sac with your own off-street parking space.

Indoor spacesKitchenOutdoor spaces

4.94 out of 5 average rating, 139 reviews

Popular amenities for Pickering family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A large tree trunk is visible in the foreground, with a bud on a branch. In the background, a wooden structure resembling a cabin is surrounded by a grassy field, fenced areas, and greenery, set against an overcast sky.
Cabin in Low Dalby

Dalby Forest Luxury Lodge

KitchenIndoor spacesComfort

4.97 out of 5 average rating, 119 reviews
Top guest favorite
A stone cottage with a red-tiled roof is visible behind a dry-stone wall. Brightly colored flowers and greenery surround a playful pig statue in the foreground. The sunny sky provides a clear view of the welcoming farmhouse and its charming surroundings.
Cottage in Newton-on-Rawcliffe

Charming farm based cottage with hot tub/sauna

Indoor spacesFamilyView

4.98 out of 5 average rating, 232 reviews
Top guest favorite
A wooden lodge is nestled within lush green woodland, surrounded by trees. The structure features a spacious deck with outdoor seating, and a Scandinavian style wood-fired hot tub is situated nearby, blending seamlessly into the natural setting.
Cabin in Rivendell

2 bedroom lodge with hot tub in private woodland

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 168 reviews
Top guest favorite
A historic building is set against a backdrop of blue sky, with seasonal flowers blooming in the foreground. Crocuses and small yellow flowers create a vibrant carpet of color across the lush, green lawn, inviting relaxation and appreciation of the natural surroundings.
Home in Langton

North Wing of Langton Hall - Grade 2 listed

Indoor spacesKitchenBackyard

4.94 out of 5 average rating, 197 reviews
Superhost
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

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

KitchenFamilyLaundry

4.9 out of 5 average rating, 197 reviews
Top guest favorite
The exterior of a shepherd's hut is displayed, featuring wooden doors that open to invite guests inside. Two rustic chairs are positioned on a gravel area, complemented by planter boxes along the edge. Rolling hills and a farmhouse can be seen in the background.
Shepherd’s hut in North Yorkshire

Moo view Luxury Shepherd’s hut

FamilyIndoor spacesWalkability

4.93 out of 5 average rating, 163 reviews
Top guest favorite
A quaint outdoor seating area is arranged with a round table and four woven chairs. A wine bottle and two glasses rest on the table. A stone wall adds texture to the setting, while a wooden door with a decorative window complements the rustic charm.
Vacation home in Harwood Dale

Wykeham Cottage, Stunning Cottage in Harwood Dale

Indoor spacesKitchenQuiet

4.96 out of 5 average rating, 190 reviews
Top guest favorite
An aerial view captures the rustic cabin surrounded by expansive green fields, with rolling hills visible in the background. The property features a red-tiled roof and a spacious gravel area for parking. Fencing encloses the garden, offering a sense of privacy and openness.
Farm stay in Broxa

The View Broxa - Luxury Lodge - Yorkshire Coast

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 187 reviews

Family- and pet-friendly home rentals

Top guest favorite
The cozy lounge area features original wood beams and a brick fireplace. A television is positioned next to a woven basket. A green sofa is paired with a chair, creating an inviting space. Natural light enters through a curtained window, complemented by a vase of flowers.
Cottage in North Yorkshire

Yorkshire cottage with private parking &EV charger

Indoor spacesFamilyHeating

4.98 out of 5 average rating, 114 reviews
Top guest favorite
The three-storey town house features a classic stone facade with large windows that allow natural light to fill the interior. The entrance includes two white doors, each framed by decorative columns, with a small set of steps leading up to them.
Home in Kirkbymoorside

The Town House

Indoor spacesKitchenTV

4.93 out of 5 average rating, 101 reviews
Superhost
Cottage in North Yorkshire

Between Coast & Moors • Pickering 2BR • Sleeps 4

KitchenFamilyLocation

4.84 out of 5 average rating, 142 reviews
Top guest favorite
A cozy suite is featured, with a spacious bed neatly made. A comfortable seating area contains a gray sofa with decorative pillows, a vintage trunk, and a piano. Natural light pours through two windows, illuminating the wooden floor and soft wall colors.
Guest suite in Nunnington

Renovated 16th century haven in North Yorks Moors

KitchenFamilyLocation

4.88 out of 5 average rating, 225 reviews
Guest favorite
A bright bedroom features a spacious bed with soft bedding, complemented by a decorative chest of drawers. Natural light floods the room, highlighting the neutral decor. A doorway leads to an en-suite bathroom, and a comfortable seating area is visible in the background.
Home in Kirkbymoorside

Oakforge Cottage, a spacious home from home.w

Indoor spacesKitchenComfort

4.9 out of 5 average rating, 476 reviews
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

Goose End Cottage, North Yorkshire

FamilyIndoor spacesCondition

4.97 out of 5 average rating, 158 reviews
Guest favorite
A charming two-story brick house features large windows with white frames, allowing ample natural light. The front entrance is marked by a light blue door, complemented by potted plants on each side. A quiet street view and neighboring houses provide a peaceful setting.
Cottage in Sinnington

Beulah House

Indoor spacesKitchenComfort

4.92 out of 5 average rating, 149 reviews
Top guest favorite
A converted stable is situated on a grassy area, surrounded by trees. The structure features a simple wooden door and a metal chimney, with a wood-burning stove visible inside. A cooking fire pit with a tripod and cauldron is placed in front of the stable on a circle of brick.
Hut in Low Dalby

DIY shed in the middle of the woods.

Indoor spacesKitchenView

4.96 out of 5 average rating, 150 reviews

Family-friendly home rentals with a pool

Guest favorite
A heated indoor swimming pool is seen, featuring clear water reflecting natural light. Large windows provide views of the surrounding garden. A pink float is positioned in the water, adding a touch of color to the serene setting.
Bungalow in York

Ellerburn Lodge

KitchenFamilyPool

4.88 out of 5 average rating, 241 reviews
Guest favorite
A cozy lounge area is furnished with a blend of comfortable seating, including a tufted blue sofa and a brown leather couch. A small wooden table displays a tea set, while a chessboard is ready for play. Natural light filters through a large window, offering a view of greenery.
Home in North Yorkshire

Cosy 2 bedroom river/coastal retreat. Heated pool.

Indoor spacesFamilyLocation

4.81 out of 5 average rating, 132 reviews
Top guest favorite
A light blue beach house is featured, set against a clear blue sky. A spacious deck is adorned with a white umbrella, while a comfortable seating area invites relaxation. Lush green grass surrounds the property, contributing to a cheerful outdoor setting.
Cabin in Filey

Secret of Eden Beach House - Pet friendly WiFi E.V

FamilyKitchenParks

4.97 out of 5 average rating, 442 reviews
Guest favorite
A balcony railing offers a clear view of the expansive green landscape that leads to the sea. Gentle slopes and distant coastline are visible under a bright blue sky, creating a serene outdoor atmosphere.
Cottage in North Yorkshire

3 bedroom cottage with fabulous sea views.

FamilyIndoor spacesHeating

4.85 out of 5 average rating, 102 reviews
Top guest favorite
The exterior of a two-story brick cottage is presented, showcasing a modern architecture with white window trims. A well-maintained lawn and hedges frame the property, while a clear blue sky with scattered clouds provides a bright backdrop.
Cottage in Filey

Willow Cottage: 3 Bed, 3 Bath, Pool, WiFi, dogs

FamilyKitchenValue

4.97 out of 5 average rating, 132 reviews
Top guest favorite
The entrance to Ivy Cottage is framed by lush greenery, featuring a welcoming white door with a modern design. Bright, red-tipped leaves contrast with the soft tones of the brick wall, creating an inviting first impression.
Cottage in North Yorkshire

Ivy Cottage -Award-Winning Complex- The Bay, Filey

Indoor spacesFamilyHospitality

4.97 out of 5 average rating, 268 reviews
Top guest favorite
A two-story cottage features a white exterior with a dark slate roof and distinctive entrance. Surrounded by landscaped gardens, the home is complemented by a tree in the foreground and neighboring buildings of varied architectural styles, showcasing a charming holiday village atmosphere.
Home in North Yorkshire

Salty Kisses, The Bay, Filey

KitchenIndoor spacesAccess

4.93 out of 5 average rating, 165 reviews
Guest favorite
A spacious living area features a light-colored corner sofa with decorative cushions, positioned near a large window that allows natural light to fill the room. A coffee table sits beside the sofa, and the kitchen area is visible in the background.
Vacation home in Cayton

2 bed holiday lodge

FamilyIndoor spacesBeach

4.94 out of 5 average rating, 124 reviews

When is the best time to visit Pickering?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,611 GYDG$38,284 GYDG$37,029 GYDG$39,121 GYDG$39,749 GYDG$40,376 GYDG$40,376 GYDG$39,540 GYDG$36,820 GYDG$36,611 GYDG$37,238 GYDG$40,586 GYD
Avg. temp3°C3°C5°C7°C10°C12°C15°C14°C12°C9°C6°C3°C

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