Holiday rentals in Pickering

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Popular amenities for Pickering holiday rentals

Stay near Pickering's top sights

Cedarbarn Farm Shop, Cafe & Miniature Railway17 locals recommend
Beck Isle Museum15 locals recommend
Spice 4 U12 locals recommend
The White Swan Inn8 locals recommend
Figaros6 locals recommend
Lidl4 locals recommend

Other great holiday rentals in Pickering

Guest favourite
Cottage in Meltham
4.97 out of 5 average rating, 123 reviews

Greens End Cottage

Lucy AlexandraRating, 5 stars2 weeks ago
Lovely house, loved the decor and touches around the place. All the beds were really comfortable, felt like we were staying in a luxury hotel. The outside table gets some lovely afternoon sun, was great to sit out after our walk. Great location for getting out walking. Loved our stay.
Top guest favourite
Home
5 out of 5 average rating, 24 reviews

Chance Escapes

SylvianRating, 5 stars1 week ago
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!
Guest favourite
Campervan/Motorhome
4.86 out of 5 average rating, 22 reviews

Seaview Retreat Crimdon Dene

LouiseRating, 5 stars2 weeks ago
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 💚
Guest favourite
Barn
4.92 out of 5 average rating, 64 reviews

Hidden Family Farm Paradise- near York & the Coast

LyndseyRating, 5 stars1 month ago
We have just returned from a stay in this wonderful barn. Pictures don’t do it justice. It’s even more beautiful than the pictures show. Great location and really peaceful. The children loved seeing the chickens and horses. Great location and would definitely recommend for families wanting to go to Whitby , Dalby Forest and the little village of Thornton Le Dale with its lovely cafes.
Guest favourite
Flat
4.92 out of 5 average rating, 48 reviews

Bel air The hideaway

KarenRating, 5 stars4 days ago
Second time staying here and loved it, so handy to everywhere and had everything we needed😀
Top guest favourite
Place to stay
5 out of 5 average rating, 39 reviews

Sunrise & Seaview with pool access

IanRating, 5 stars7 months ago
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.
Guest favourite
Home
4.95 out of 5 average rating, 43 reviews

Castle and Mount Views Scarborough

StevenRating, 5 stars6 months ago
Short stay but everything was as expected and will definitely book again if another reason to visit the area arises.
Top guest favourite
Home
5 out of 5 average rating, 22 reviews

Character 5 bedroom property

NeilRating, 5 stars4 months ago
If you’re staying in Pocklington then this house is fantastic. Huge! Clean! Warm and cosy. All the mod cons. Really really exceeded our expectations. It’s just a couple of minutes walk from Market Place. Only comment is that maybe there should be fans in all the bathrooms…otherwise, it’s like Dr. Who’s Tardis…way bigger than you think. Loved it.

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.

Destinations to explore

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