Pickering Holiday Rentals

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Holiday Rentals in Pickering

BBQ/picnic area
Middlehead Cottages at Cropton Forest
3.0 star property
10.0 out of 10, Exceptional, (23)
"Our second time here and definitely not our last, everything you need for a comfortable weekend away. We love the location, the DVD collection, the hot tub and the log fires. Wish we could stay for longer! Really good value too. Thanks x "
Middlehead Cottages at Cropton Forest
Tent, Shared Bathroom | Exterior
The Little Hide - Grown Up Glamping
9.4 out of 10, Exceptional, (116)
"Have never been to a Glamping pod before but would absolutely visit the little hide again. The pod was a good size and had everything we needed. Great location and the showers/ toilets are well kept. Would come back next time and will bring a disposable bbq to use at the shared area."
The price is NZ$166
includes taxes & fees
2 Jun - 3 Jun
The Little Hide - Grown Up Glamping
Beach
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
9.8 out of 10, Exceptional, (226)
"What a beautiful place to stay. Brilliant location, magic views and very peaceful."
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
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Cottage, Private Bathroom | Private kitchen
Five Star Stays
4.0 star property
9.8 out of 10, Exceptional, (98)
"Cottage was amazingly my really clean, and the decor was amazing will definitely stay here again "
The price is NZ$248
includes taxes & fees
19 May - 20 May
Five Star Stays
Aerial view
40ft x 20ft luxury holiday lodge near Scarborough; 3 bed, sleeps 6, hot tub
9.8 out of 10, Exceptional, (206)
"The nice property, has everything you need, big lodge, nice hot tube.I wish to book again!"
40ft x 20ft luxury holiday lodge near Scarborough; 3 bed, sleeps 6, hot tub
Penthouse, 2 Bedrooms, Sea View
The Sands - Sea Front Apartments
5.0 star property
9.8 out of 10, Exceptional, (119)
"Great location with helpful and friendly staff but it was very difficult to get a decent flow of hot water in the shower."
The price is NZ$1,138
includes taxes & fees
2 Jun - 3 Jun
The Sands - Sea Front Apartments
Terrace/patio
Glendevon Cottage - Enjoy 2-Night Stays
9.8 out of 10, Exceptional, (117)
"Staithes is mine and my partner's favourite place in the UK. We have stayed in Staithes a few times now and I can honestly say I would recommend this cottage to anyone. The location is perfect with a bit of a sea view from the bedroom window. The cottage has a lovely cosy feel to it, beds are really comfy and has everything you need for a short/ long stay. Thank you Anne!"
Glendevon Cottage - Enjoy 2-Night Stays
Beach nearby
Apartment Aquamarine, the Bay Filey
9.4 out of 10, Exceptional, (86)
"Fabulous"
Apartment Aquamarine, the Bay Filey
Deluxe Apartment, Private Bathroom, Sea View (2) | Miscellaneous
Sea View House
3.5 star property
8.6 out of 10, Excellent, (27)
"The property has some maintenance issues that need sorting. Carpet to bathroom and bedroom is loose. Its a curved staircase and its very dangerous. I asked about fixing it which i was told would be done by handyman. All he did was tuck it in so within a day was loose again which caused an accident. Bathroom is damp and paint and plaster is peeling off. Few other bits as well need sorting. Its a nice central place with lovely views. The owner has said it is getting an overhaul soon and all these...
The price is NZ$255
includes taxes & fees
19 May - 20 May
Sea View House
Exterior
Whitby Bridge Luxury Apartments
3.5 star property
7.8 out of 10, Good, (7)
"Fantastic location, apartment well equipped, quality bed linen and towels "
The price is NZ$329
includes taxes & fees
20 May - 21 May
Whitby Bridge Luxury Apartments
Property grounds
The County Boutique Apartment
10.0 out of 10, Exceptional, (120)
"A1+++ Everything you need...just pack a toothbrush! Highly recommended Thanks!"
The County Boutique Apartment
Property grounds
Beach House "Just Beachy" Sleeps 4, WiFi, Netflix, Pet Friendly, close to beach
10.0 out of 10, Exceptional, (23)
"We spent a long weekend in this lovely beach house with its modern decor and many facilities. It was well placed in the holiday village near to the pub and shop and path to the beach. The path itself was steep in parts but manageable. There is a lovely walk along the beach to Filey. A wondered stay."
Beach House "Just Beachy" Sleeps 4, WiFi, Netflix, Pet Friendly, close to beach
Fridge, microwave, oven, stovetop
⭐️EXCEPTIONAL⭐️ONE BEDROOM APARTMENT WHITBY!😍ABBEY VIEWS! 3PM CHECK IN SLEEPS 4
10.0 out of 10, Exceptional, (109)
"The flat is well appointed, clean, and very quiet. It is steps away from the seaside pavilion as well as the dockside attractions. Even better was the prompt and friendly communications with the owner who instilled a sense of security and welcome."
⭐️EXCEPTIONAL⭐️ONE BEDROOM APARTMENT WHITBY!😍ABBEY VIEWS! 3PM CHECK IN SLEEPS 4
Outdoor dining
Family and pet friendly converted barn in a peaceful rural setting
9.8 out of 10, Exceptional, (207)
"Long weekend stay but not long enough. Cottage in a great place for visiting the area. Kids and dogs loved it. Met the alpacas close up."
Family and pet friendly converted barn in a peaceful rural setting
Beach nearby
Filey. Active leisure or relaxing beach holiday.
9.8 out of 10, Exceptional, (231)
"A perfect base to explore, close to the sea, beautiful house and fantastic relaxed setting. Would love to stay again."
Filey. Active leisure or relaxing beach holiday.
Exterior
Situated on the Whitby Lighthouse site has a raised deck giving wonderful views.
9.6 out of 10, Exceptional, (4)
"Absolutely lovely stay in a unique property. Such a beautiful place and we loved Whitby too."
Situated on the Whitby Lighthouse site has a raised deck giving wonderful views.
View from room
Apartments in Skinningrove, Cattersty Sands Beach
2.0 star property
5.4 out of 10, (3)
"1. Getting difficult to.find the exact location of property, its helpful if mentioned the building name. 2.Whole night struggled to run the heating but didnt work survived without heating. 3. Wifi id provided not available in the premises. "
Apartments in Skinningrove, Cattersty Sands Beach
Interior
Cottage With Sea Views
9.6 out of 10, Exceptional, (132)
"The property was in a great location and the view was spectacular!"
Cottage With Sea Views
Beach
Cottage in the centre of Whitby - beautiful coastal and Abbey views
9.8 out of 10, Exceptional, (87)
"Great location and well equipped property. We had a great stay. Thanks Hilda."
Cottage in the centre of Whitby - beautiful coastal and Abbey views
Beach nearby
Brigg End View - a cottage that sleeps 4 guests in 2 bedrooms
9.8 out of 10, Exceptional, (6)
Brigg End View - a cottage that sleeps 4 guests in 2 bedrooms
Don't see what you're looking for?
See all available properties in Pickering
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.

Other types of properties in Pickering you may be interested in

Front of property - evening/night
White Horse Farm Inn
3.5 star property
8.2 out of 10, Very good, (82)
"Food was fantastic only issue we had bathroom lock was damaged advised them straight away and guttering leaked as it raining kept me awake most of the night ( advised them the next day ) "
The price is NZ$257
includes taxes & fees
26 May - 27 May
White Horse Farm Inn
Standard Twin Room
Leonardo Hotel Middlesbrough
4.0 star property
8.6 out of 10, Excellent, (826)
"Nice clean hotel However when ordering food in the restaurant two of the items on the menu were not available"
The price is NZ$138
includes taxes & fees
16 Jun - 17 Jun
Leonardo Hotel Middlesbrough
Bar (on property)
The Royal Hotel
3.0 star property
8.0 out of 10, Very good, (431)
"Had a wonderful one night stay"
The price is NZ$122
includes taxes & fees
2 Jun - 3 Jun
The Royal Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Pickering holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Pickering. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Pickering. Seeing all the best attractions is bound to make you fall in love with Pickering. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Pickering short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Pickering?

Yes, there are holiday rentals close to the most popular sights in Pickering, 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.

How many holiday rentals are there in Pickering?

Expedia has 49 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 York Moors National 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.

Recent reviews of Pickering properties
Expedia verified reviews