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, (117)
"Really enjoyed our stay, very cozy and peaceful in nature. A lovely getaway."
The price is NZ$166
per night
2 Jun - 3 Jun
The Little Hide - Grown Up Glamping
Penthouse, 2 Bedrooms, Sea View
The Sands - Sea Front Apartments
5.0 star property
9.8 out of 10, Exceptional, (120)
"We enjoyed our stay at the Sands apartment. It was a nice area with lovely views looking out to north beach. We stayed in a duplex apartment on the ground floor and felt the bedrooms were a bit small and cramped. Not enough storage space eg. No chest of drawers in the main bedroom and only 10 hangers between two adults. We lived out our cases. The outside patio area and chairs were filthy and not cleaned for our arrival. Having seen inside another two bed On the 4th floor it was far superior in...
The price is NZ$1,145
per night
2 Jun - 3 Jun
The Sands - Sea Front Apartments
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Beach
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
9.8 out of 10, Exceptional, (227)
"Wildgoose Cottage was a fabulous, away from it all break. The only noise we heard was nature, cows, pheasant and lots of birds. We were lucky to see a deer with a fawn and boxing hares. This is a very relaxing place to stay but a good 45 minutes walk to the centre of Whitby either along the road or the Cleveland Way."
Beautiful Cosy Cottage On The Cliff Top With Stunning Sea Views
Aerial view
40ft x 20ft luxury holiday lodge near Scarborough; 3 bed, sleeps 6, hot tub
9.8 out of 10, Exceptional, (207)
"Had the most wonderful time at Diane’s den! Couldn’t fault it! Will be coming back"
40ft x 20ft luxury holiday lodge near Scarborough; 3 bed, sleeps 6, hot tub
Cottage, Private Bathroom | Private kitchen
Five Star Stays
4.0 star property
9.8 out of 10, Exceptional, (98)
"It was great location, outskirts of popular beach attractions "
The price is NZ$281
per night
27 May - 28 May
Five Star Stays
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$219
per night
27 May - 28 May
Sea View House
Beach nearby
Apartment Aquamarine, the Bay Filey
9.4 out of 10, Exceptional, (87)
"Good Value , as advertised relaxing few days away, would use again On site pub prices very high, excellent swimming pool ideal for young families, site very popular with dog owners"
Apartment Aquamarine, the Bay Filey
Property grounds
Beach House "Just Beachy" Sleeps 4, WiFi, Netflix, Pet Friendly, close to beach
10.0 out of 10, Exceptional, (24)
"Everything was fantastic, a brilliant place to sit back and enjoy life."
Beach House "Just Beachy" Sleeps 4, WiFi, Netflix, Pet Friendly, close to beach
Exterior
Whitby Bridge Luxury Apartments
3.5 star property
7.8 out of 10, Good, (8)
"Fantastic location, apartment well equipped, quality bed linen and towels "
The price is NZ$373
per night
2 Jun - 3 Jun
Whitby Bridge Luxury Apartments
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
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
Rainbow Cottage - A home from home in the heart of Whitby
9.6 out of 10, Exceptional, (98)
"Perfect for a short break away. Clean, had everything we needed and the location is brilliant."
Rainbow Cottage - A home from home in the heart of Whitby
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
Beach
Cottage in the centre of Whitby - beautiful coastal and Abbey views
9.8 out of 10, Exceptional, (88)
"Amazing location with a great view."
Cottage in the centre of Whitby - beautiful coastal and Abbey views
Beach nearby
Filey. Active leisure or relaxing beach holiday.
10.0 out of 10, Exceptional, (208)
"We had all we needed,had a very enjoyable stay. The only thing that spiolt it was the weather."
Filey. Active leisure or relaxing beach holiday.
Beach nearby
Cosy Cottage in Staithes. North Yorkshire Moors Coast. Weekend Breaks Available
9.0 out of 10, Wonderful, (43)
"cottage could do with a good clean but other then that it was brilliant ."
Cosy Cottage in Staithes. North Yorkshire Moors Coast. Weekend Breaks Available
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
Exterior
A luxury country cottage by the sea, 5 ensuite bedrooms, walkable to the harbour
10.0 out of 10, Exceptional, (64)
"Beautiful, spacious renovated old mill. Great outdoor space overlooking private stream. Luxury bedrooms with ensuite shower rooms. Large kitchen, dining room and 2 lounge areas. An amazing stay with everything you could possibly want in a quiet, secluded area, close to Whitby. Would thoroughly recommend and wiuld definitely stay again if in the area. Thanks again The Australia and English group of friends"
A luxury country cottage by the sea, 5 ensuite bedrooms, walkable to the harbour
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, (83)
"Great place to stay with wonderful view of the valley. Food was excellent. Wonderful service from Liam and Stuart who went out of their way to help us."
The price is NZ$197
per night
27 May - 28 May
White Horse Farm Inn
Bar (on property)
The Royal Hotel
3.0 star property
7.8 out of 10, Good, (446)
"The property has aged wonderfully and takes you back to old time Whitby. The stay at the royal hotel is unique in and of itself. The views it offers are outstanding; of the sea and the abbey atop the hill. "
The price is NZ$111
per night
16 Jun - 17 Jun
The Royal Hotel
Exterior
Britannia Grand Hotel Scarborough
3.0 star property
5.8 out of 10, (1862)
"Our room was large and comfortable, had armchsirs, bedside lights, bath shower. Staff were friendly and helpful."
The price is NZ$87
per night
3 Jun - 4 Jun
Britannia Grand Hotel Scarborough
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