
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.

Diamond Den- a quiet, peaceful and private haven.
Situated in the extremely peaceful village of Butterwick, just a few moments walk to the river rye and bridge, Diamond Den is the perfect retreat. Being at the foot of the Howardian Hills provides a wealth of walking opportunities and we are just a short drive away from some spectacular market towns, including Helmsley (8m) Malton( 5.4m), Ampleforth (9.7m) and Pickering (8.5m). You will have your own private garden space and parking. ACCESS TO THE SLEEPING AREA IS UP A LADDER- PLEASE SEE IMAGES

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.

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.

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.

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.

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.

Strolling Distance To Pickering Town Centre
Enjoy a clean, comfortable, experience at this peacefully located, budget friendly holiday home. Just a very short stroll away from Pickering town centre with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking subject to availability or car park with ev chargers less than 300 meters away. Secure garage for bikes and/or motorcycles

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/

2 bedroom lodge with hot tub in private woodland
Delightful 2 bedroom lodge set in private woodland, with decking, outdoor seating, firepit and a Scandinavian style wood fired hot tub for guests private use. Enjoy the sounds of nature when you stay in this unique place. Secluded location with easy access to the North Yorkshire Moors National Park and walking distance to the pretty market town of Pickering. Moors, coast, forest nearby and a steam railway literally on the doorstep. No Wi-Fi and patchy mobile signal - the perfect escape!

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.

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.

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.
Popular amenities for Pickering family-friendly rentals
Family-friendly home rentals with a hot tub

Cosy Rural Cabin with Private Hot Tub

Wykeham Cottage, Stunning Cottage in Harwood Dale

Stunning rural shepherds hut

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

Cozy Stay at Animal Sanctuary

Escape into Nature - Woodpecker

The Highlander

Luxury Cottage close to Castle Howard with hot tub
Family- and pet-friendly home rentals

Grooms Cottage by Sheriff Hutton Castle Near York

The Pump House @ Pockthorpe

The Little House Peaceful & self-contained

Farm Cottage with Stunning Views.

Spacious character historic cottage

Elstree Escape (private annexe, inc parking)

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

Seaside escape close to North Bay, Scarborough
Family-friendly home rentals with a pool

Jubilee Hall apartment 2 - Modern and spacious

Salty Kisses, The Bay, Filey

Well located lodge

Relax at lovely Collie Cottage, The Bay Filey

Hot Tub Pet Friendly York

Yorkshire Coast Retreat The Bay Filey Wifi Pets

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

Clara's Den at The Bay, Filey
Quick stats about holiday rentals that are family-friendly in Pickering
Total rentals
110 properties
Nightly prices starting at
$78 SGD before taxes and fees
Total number of reviews
3.2K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
100 properties include access to wifi
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- Flamingo Land Resort
- The Bay Filey
- Harewood House
- Fountains Abbey
- Durham Cathedral
- National Railway Museum
- Royal Armouries Museum
- North Yorkshire Water Park
- York Castle Museum
- Hartlepool Sea Front
- Cayton Bay
- Saltburn Beach
- Studley Royal Park
- Scarborough South Cliff Golf Club
- Locomotion
- Ganton Golf Club
- Ryedale Vineyards
- York Art Gallery
- Castle Howard
- Scarborough Beach
- Filey Beach