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Pickering Holiday Rentals

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Our top choices for Pickering holiday rentals

Cottage in Pickering

Craven Garth Cottages
3.0 star property
9.4 out of 10, Exceptional, (46)
"Really nice place,friendly landlord and very helpful"
United Kingdom
Corin
The price is NZ$522
includes taxes & fees
10 Jan - 11 Jan 2026
Craven Garth Cottages

Cottage in Pickering

5 Church View
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is NZ$774
includes taxes & fees
3 Jan - 4 Jan 2026
5 Church View
10.0 out of 10, Exceptional, (1)
"If you are looking for somewhere to stay in Pickering, 2 minutes from the town centre, this is for you. We were surprised to find that the house is on 4 floors, one bedroom in the basement; kitchen, front room and toilet on the ground floor; shower, bath, toilet and living room on the second floor; two bedrooms (double and two singles) on the top floor. The stairs are quite steep and probably not suitable for young children but fine for adults. There is no on-site parking but just across the...
United States
Spencer Greystrong
The price is NZ$685
includes taxes & fees
3 Jan - 4 Jan 2026
2 bedroom accommodation in Pickering
9.0 out of 10, Wonderful, (8)
"Most enjoyable, well appointed cottage comfortable central to the town. Plenty to do and see with the railway nearby. We are looking forward to coming back next year. The Young family. "
United Kingdom
Sonia Y.
The price is NZ$486
includes taxes & fees
15 Jan - 16 Jan 2026
2 bedroom accommodation in Pickering
10.0 out of 10, Exceptional, (1)
"Beautiful property. Everything you could want to make the stay enjoyable was provided. Lovely welcome pack. Excellent communication. Great location for exploring inland and the coast. Would recommend to anybody"
United States
Kathy S.
The price is NZ$1,182
includes taxes & fees
6 Jan - 7 Jan 2026
Luxury Cottage nestled in the Heart of Pickering - Pet Friendly (FREE)
The price is NZ$1,252
includes taxes & fees
5 Jan - 6 Jan 2026
Honey Pot Barn - Escape for Two
2.0 star property
Romantic woodland cabin with private hot tub and moorland views

Cottage in Pickering

Spire View
3.0 star property
The price is NZ$569
includes taxes & fees
2 Jan - 3 Jan 2026
Spire View

Cottage in Pickering

Ghyll Cottage
3.5 star property
The price is NZ$699
includes taxes & fees
5 Jan - 6 Jan 2026
Ghyll Cottage

Cottage in Pickering

Hogwarts Cottage
3.0 star property
8.0 out of 10, Very good, (2)
"Only concern was parking.apart from thatvspot on"
United Kingdom
Paul
The price is NZ$718
includes taxes & fees
4 Jan - 5 Jan 2026
Hogwarts Cottage

Cottage in Pickering

Dovecote
2.0 star property
The price is NZ$857
includes taxes & fees
3 Jan - 4 Jan 2026
Dovecote

Cottage in Pickering

Farm Yard Cottage
3.5 star property
The price is NZ$819
includes taxes & fees
6 Jan - 7 Jan 2026
Farm Yard Cottage

Cottage in Pickering

Gateside
3.0 star property
The price is NZ$857
includes taxes & fees
2 Jan - 3 Jan 2026
Gateside

Cottage in Pickering

Bute Cottage
3.0 star property
The price is NZ$1,450
includes taxes & fees
5 Jan - 6 Jan 2026
Bute Cottage

Cottage in Pickering

Derwent House
3.0 star property
The price is NZ$923
includes taxes & fees
2 Jan - 3 Jan 2026
Derwent House

Cottage in Pickering

Ducky's
3.5 star property
The price is NZ$902
includes taxes & fees
2 Jan - 3 Jan 2026
Ducky's

Cottage in Pickering

1 The Old Methodist Chapel
3.5 star property
The price is NZ$1,114
includes taxes & fees
5 Jan - 6 Jan 2026
1 The Old Methodist Chapel

Cottage in Pickering

Sixpence Cottage
3.0 star property
Sixpence Cottage

Cottage in Pickering

Brewers Cottage
3.0 star property
The price is NZ$815
includes taxes & fees
6 Jan - 7 Jan 2026
Brewers Cottage

Cottage in Pickering

The Cottage
3.0 star property
The price is NZ$810
includes taxes & fees
4 Jan - 5 Jan 2026
The Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pickering Hotel Reviews

Find out more about Pickering

Everything you need to know about Pickering holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pickering holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pickering holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pickering holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pickering. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pickering holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pickering holiday rentals we have selected for you start as low as NZ$127 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pickering rentals

At Expedia, we put the best Pickering holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pickering rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pickering holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pickering. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Pickering?

Yes, there are holiday rentals in Pickering close to North Yorkshire Moors Railway, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the gardens in Pickering. Make sure you have time to check out the forests and theme park during your trip.

What are some of the best holiday rentals that Pickering has to offer?

Cottage in the centre of Whitby - beautiful coastal and Abbey views : This holiday home rental outside of Pickering offers a fireplace, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Pickering?

Expedia has 35 holiday rentals for your stay in Pickering.

What’s there to see and do in Pickering?

Cultural attractions include Beck Isle Museum and Gillies Jones Glass, whereas Dalby Forest Visitor Centre and North Riding Forest Park are a couple of picturesque spots to enjoy the outdoors. North Yorkshire Moors Railway and Rosedale Abbey are other places to visit while you're in town.

What’s a holiday rental in Pickering like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pickering. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip.