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

Greens End Cottage
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.

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!

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 💚

Hidden Family Farm Paradise- near York & the Coast
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.

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

Sunrise & Seaview with pool access
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.

Character 5 bedroom property
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.
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- Flamingo Land Resort
- Harewood House
- Durham Cathedral
- Royal Armouries Museum
- Fountains Abbey
- Scarborough Beach
- North Yorkshire Water Park
- Locomotion
- National Railway Museum
- Cayton Bay
- Saltburn Beach
- Filey Beach
- Whitby Beach
- Hartlepool Sea Front
- York Castle Museum
- Ganton Golf Club
- York Art Gallery
- Scarborough South Cliff Golf Club
- Ryedale Vineyards
- Studley Royal Park