
Holiday rentals in Pickering
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Top-rated holiday rentals in Pickering
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Other great holiday rentals in Pickering

Chance Escapes
Absolutely perfect stay. The house is such a great size and layout, especially for a family. Great sized garden for children & everyone kept happy with so many televisions...! Some really good and helpful recommendations of things to do for the children. Overall, not a single negative or complaint I can think of!

Brimham Retreat holiday home Lido Leisure Park 🐶✅
Great caravan - perfect for what our family needed for a few nights away from home. Would definitely recommend. Thank you.

Seaview Retreat Crimdon Dene
Beautiful caravan and very clean. Looks exactly like the photos. Well decorated and little extras. really helpful things like salt and vinegar and shower gel. right on the sea front with a 10 walk to get feet on the sand. Beach was amazing really peaceful and lovely sunrise view. A lovely few days stay 💚

Durham lodge North Yorkshire
Lovely, clean, spacious lodge in a lovely setting with a perfectly placed hot tub. The lodge meet all our requirements. Plenty of storage space, extra bedding provided and all the essentials. Highly recommended.

Hidden Family Farm Paradise- near York & the Coast
This is perfect for anyone who just wants to be out the way with no one around it was definitely what we needed! The kids loved going out and seeing the horses and the place was just beautiful inside and out. Would love to have a reason to come back again. My partner had a stroke in July so struggles in places too busy so he was in his element here 🥰

Bel air The hideaway
Second time staying here and loved it, so handy to everywhere and had everything we needed😀

Sunrise & Seaview Exclusive area . No 8 The Sands
Another lovely stay in Rachel's luxury caravan away from all the hustle and bustle, we have now stayed four times in the past twelve months and never once had a problem thank you rachel from Ian and Christine.

Castle and Mount Views Scarborough
Short stay but everything was as expected and will definitely book again if another reason to visit the area arises.
Quick stats about holiday rentals in Pickering
Total rentals
120 properties
Nightly prices starting at
£30 before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Your guide to Pickering
Welcome to Pickering
Lying at the southern border of the dramatic North York Moors, Pickering is an ancient market town that can trace its roots to 270 BCE. St Peter and St Paul’s church was built in Saxon times, and contains some of the country’s most complete medieval wall paintings; Pickering Castle was begun by William the Conqueror. You can still walk around the ruins of its motte-and-bailey fortress (used by no fewer than six English kings), while the Beck Isle Museum offers a chance to see everyday life as it’s been lived here in more recent centuries.
The town’s marketplace and high street are still the thriving hub of the community, full of independent shops, cafes, and businesses from bakeries to antique stores, while the natural splendour (and glorious isolation) of the moors are practically on the doorstep. And if that’s not enough to quicken your pulse, you can always visit the nearby theme park Flamingo Land.
The best time to stay in a holiday rental in Pickering
The neighbouring North York Moors are at their most stunning in summer and autumn, when they’re ablaze with pink and purple heather and busy with bees, butterflies, and other colourful wildlife, making it an ideal time to stay in one of the area’s holiday cottages. Summer is also the warmest time to be walking on the moors, although temperatures can be unpredictable, so it’s always worth packing for all conditions and making sure you’ve checked the forecast before you head out. Pickering’s famous steam railway usually opens seasonally from March, although there have been limited winter services in recent years; the surrounding countryside can be particularly beautiful if you’re lucky enough to see it covered in snow. In October, Pickering hosts a Railway in Wartime weekend, when the streets of the town revert to 1940s style and WWII reenactments take place.
Top things to do in Pickering
Newbridge Park
Right below the towering stone walls of Pickering Castle sits this forested community park, whose woodland has been restored by local volunteers. It’s a great area for walking, and there’s also plenty here for mountain bikers, with cycle trails, a jump park, and a pump track. They’ve even turned a disused quarry into a pleasant picnic area.
North Yorkshire Moors Railway
This historic steam railway is one of the best in the country, and Pickering is its southern terminus. A ride along its 24-mile tracks will take you through beautiful Yorkshire countryside, where you’ll stop at a sequence of lovely villages, all the way to Whitby on the east coast. Even if you’re not planning a journey, it’s worth a visit to the station, whose vintage tearoom serves fresh pies and scones.
Kirk Theatre
There’s a real tradition of theatre-going in Pickering — the small town manages to maintain no fewer than three venues — and the Kirk is at its heart. Its home, a once-derelict Wesleyan chapel, is part of the town’s fascinating religious history as a centre for nonconformist believers in the 19th century, from Methodists to Quakers.
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