
Family-friendly vacation rentals in Pickering
Find and book unique family-friendly homes on Airbnb
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$12,556 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.

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

Dalby Forest Luxury Lodge
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Secluded 2 bedroom cabin with wood fired hot tub
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Charming farm based cottage with hot tub/sauna
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Storey Corner - Where memories are made
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Luxury Country Cottage Hot Tub Spa Retreat | York
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Luxury Cottage close to Castle Howard with hot tub
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North Wing of Langton Hall - Grade 2 listed
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3 Railway Cottage Pickering , Hot Tub, Pets all'd
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Family- and pet-friendly home rentals

Between Coast & Moors • Pickering 2BR • Sleeps 4
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Lovely cottage for N. York Moors & Steam Trains
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2 bed Cottage Pickering, Priv Parking, Logburner
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DIY shed in the middle of the woods.
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Yorkshire cottage with private parking &EV charger
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Highfield Annex with off St Parking in Keldholme
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Beulah House
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The Courtyard Annexe (Please read all description)
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Family-friendly home rentals with a pool

The View Broxa - Luxury Lodge - Yorkshire Coast
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Ellerburn Lodge
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Secret of Eden Beach House - Pet friendly WiFi E.V
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Cosy 2 bedroom river/coastal retreat. Heated pool.
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Sandy Toes, The Bay, Filey
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Willow Cottage: 3 Bed, 3 Bath, Pool, WiFi, dogs
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Pool, playroom, animals & more in a 2-bed cottage
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One bedroomed cottage with swimming pool.
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When is the best time to visit Pickering?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$36,623 GYD | G$38,297 GYD | G$37,041 GYD | G$39,134 GYD | G$39,762 GYD | G$40,390 GYD | G$40,390 GYD | G$39,553 GYD | G$36,832 GYD | G$36,623 GYD | G$37,251 GYD | G$40,599 GYD |
| Avg. temp | 3°C | 3°C | 5°C | 7°C | 10°C | 12°C | 15°C | 14°C | 12°C | 9°C | 6°C | 3°C |
Destinations to explore
- Yorkshire Coast
- Filey Beach
- Bempton Cliffs
- Harewood House
- Fountains Abbey
- York Castle Museum
- Bramham Park
- Durham Cathedral
- Temple Newsam Park
- York University
- York Minster
- Scarborough Beach
- Teesside University
- The Deep
- Peasholm Park
- Bridlington Spa
- First Direct Arena
- Durham University
- Blue Dolphin Holiday Park - Haven
- Richmond Castle
- Lightwater Valley
- Kynren
- Howardian Hills Area of Outstanding Natural Beauty
- Skirlington Market





