Family-friendly holiday rentals in Pickering

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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 favourite
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 Pickering
4.82 out of 5 average rating, 306 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 favourite
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 Pickering
4.91 out of 5 average rating, 350 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 favourite
The wooden cabin features a covered raised decking area with steps leading to the entrance. Large windows enhance natural light, while the rustic finish blends with the surrounding greenery. The structure is set against a cloudy sky, surrounded by a fenced area with ample grass.
Farm stay in Scarborough
4.98 out of 5 average rating, 420 reviews

Serenity

Our second of three luxury handcrafted log cabins, set on a working farm in the heart of Dalby Forest. (Also see Dahlia Cabin on a separate listing.) Perfect for couples or families. Our cozy, heated cabin has a fridge, kettle, and an ensuite bathroom with heated towel rails. Enjoy the stunning views from the covered raised decking area. Close to Dalby visitors center and 30 miles of amazing mountain bike trails. We provide a continental breakfast brought to the door, and a gas bbq for cooking.

Top guest favourite
A spacious living area features a green sectional sofa and a complimentary armchair. A coffee table is centered on a woven rug, with a decorative ladder parallel to a shelf adorned with plants. Large windows allow ample natural light, framed by green accents.
Home in Pickering
4.97 out of 5 average rating, 113 reviews

The Bothy

Adults only/no pets..our Ethos ..to make your visit relaxing, recharge your batteries, revisit..all in a peaceful setting but don’t take our word for it..read our Reviews! We may not have cooking facilities but Pickering has some great eateries and pubs…what we do have is a kettle/coffee machine/fridge/BBQ Discounts for sun-thurs and early bookings…don’t delay book today! Come to beautiful North Yorkshire so much to see and do you may never want to leave! A warm welcome awaits you at The Bothy

Top guest favourite
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 Pickering
4.97 out of 5 average rating, 117 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.

Guest favourite
A charming cottage exterior is surrounded by lush greenery, featuring a stone facade and a blue front door. Tall trees and neatly trimmed bushes frame the entrance, while wildflowers and grass add a natural touch to the pathway. The peaceful setting invites exploration.
Cottage in Pickering
4.84 out of 5 average rating, 192 reviews

Cosy one bedroom cottage in Pickering

This lovely cottage is nestled in the centre of the beautiful market town of Pickering, Relax at this charming cottage which offers easy access to the enchanting landscapes of the North Yorkshire Moors and the nearby towns and coast. Whether you visit the iconic North Yorkshire Moors Railway, attend a concert at the Scarborough Open Air Theatre, or spend a day at the beach or exploring Whitby and the Moors. If you are seeking relaxation or adventure, this unique getaway is the perfect choice.

Top guest favourite
A detached holiday cottage features a red front door and distinctive round window, set against a backdrop of textured brick walls. The surrounding area is landscaped with greenery, and gravel provides off-road parking in front of the building.
Cottage in Pickering
4.93 out of 5 average rating, 358 reviews

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE

Detached holiday cottage Sleeps two (ONE DOUBLE BED) FREE WIFI Off road parking En-suite bathroom Fully equipped kitchen TV and fridge freezer Microwave Ideal location for all local attractions 2 minute walk into Pickering and local pubs, restaurants and shops Quotes from past guests: it's just perfect/best cottage we've stayed in/everything is so welcoming/ location is fantastic Places to visit in North Yorkshire http://www.iknow-yorkshire.co.uk/attractions/north_yorkshire/

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 Pickering
4.82 out of 5 average rating, 501 reviews

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.

Top guest favourite
The exterior showcases a charming stone cottage with large windows, allowing natural light to fill the interior. A gated entrance leads to a gravel path, framed by a low stone wall and greenery, offering a tranquil setting in a quiet area.
Cottage in Pickering
4.98 out of 5 average rating, 171 reviews

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, Ninja Air Fryer, 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 car parking public chargers nearby 1 x small dog subject to fee

Guest favourite
A view of tranquil rooftops showcasing the unique character of the surrounding buildings with a mix of red brick and tile. Lush greenery and trees provide a soft backdrop, highlighting the natural beauty found in this serene rural area.
Home in Pickering
4.89 out of 5 average rating, 140 reviews

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. A 1 minute walk to forest walks 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.

Top guest favourite
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 Pickering
4.93 out of 5 average rating, 389 reviews

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.

Top guest favourite
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 Pickering
4.94 out of 5 average rating, 109 reviews

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.

Popular amenities for Pickering family-friendly rentals

When is the best time to visit Pickering?

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

  • Total holiday rentals

    Explore 120 holiday rentals in Pickering

  • Nightly prices starting at

    Pickering holiday rentals start at $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,630 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    120 of Pickering holiday rentals include wifi 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!