A coastal scene with a frozen waterway, a lighthouse, and a rocky shoreline.

Pickering Holiday Rentals

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Our top choices for Pickering holiday rentals

King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg
Pickering
10.0 out of 10, Exceptional, (29 reviews)
"Very warm and tidy house. Host was very responsive. Highly recommended."
United Kingdom
Simon H.
The price is NZ$713
includes taxes & fees
6 July - 7 July
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard

Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard
Pickering
The price is NZ$819
includes taxes & fees
19 July - 20 July
Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard

Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park

Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park
Pickering
10.0 out of 10, Exceptional, (7 reviews)
"The house is beautiful, clean, and quiet. The host was very responsive and answered all my questions promptly. We had a great stay."
United States
Manouchka M.
The price is NZ$945
includes taxes & fees
13 July - 14 July
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park

Cozy Entire Apartment - Quiet & Privacy

Cozy Entire Apartment - Quiet & Privacy
Pickering
8.0 out of 10, Very good, (2 reviews)
"I highly recommend this place. It far exceeds the pictures the level of modem comfort , appeal and cleanliness. The location, additional is very central. Very close to prominent attractions like The Marina, The Toronto Zoo, Lake Eerie and lovely botanical gardens. I am already planning my next trip for October and this will be my choice of accommodation! Seldom do you go to an air b and b and there’s washer and dryer with detergent provided. I was blown away by this cozy place as described. The...
United States
Suzette M.
The price is NZ$509
includes taxes & fees
13 July - 14 July
Cozy Entire Apartment - Quiet & Privacy

Modern Suite, Sleeps 6, Private Entry,Free Parking, 40 min to Downtown Toronto .

Modern Suite, Sleeps 6, Private Entry,Free Parking, 40 min to Downtown Toronto .
Pickering
10.0 out of 10, Exceptional, (2 reviews)
"The property was PERFECT! It was clean and well decorated. It reminded me of home. The host is very responsive"
United States
Angela
The price is NZ$317
includes taxes & fees
10 July - 11 July
Modern Suite, Sleeps 6, Private Entry,Free Parking, 40 min to Downtown Toronto .

Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish

Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish
Pickering
10.0 out of 10, Exceptional, (5 reviews)
"Easy walking distance to GO station to get into Toronto. Easy walk over a pedestrian bridge to the new Pickering City Centre and Movie Theatre. Brand new building with excellent security and a concierge. Nice gym. Walking distance to the waterfront trail. The only negative is that there is currently building construction next door so it is a bit loud during the day. It is quiet after about 5 pm and overnight."
Canada
Fiona
The price is NZ$493
includes taxes & fees
7 July - 8 July
Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish

Stylish Newly Built Pickering Family Home

Stylish Newly Built Pickering Family Home
Pickering
The price is NZ$846
includes taxes & fees
5 July - 6 July
Stylish Newly Built Pickering Family Home

Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard

Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard
Pickering
10.0 out of 10, Exceptional, (1 review)
"Place was amazing. Super clean. Jasmine was super helpful with any questions I had and also had great recommendations."
United States
Branden T.
The price is NZ$521
includes taxes & fees
7 July - 8 July
Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard

A beautiful Walkout basement

A beautiful Walkout basement
Pickering
9.0 out of 10, Wonderful, (4 reviews)
"Great place and quiet neighborhood. "
United States
Lance C.
The price is NZ$496
includes taxes & fees
6 July - 7 July
A beautiful Walkout basement

Cozy & modern apartment in Pickering

Cozy & modern apartment in Pickering
Pickering
10.0 out of 10, Exceptional, (4 reviews)
"We had a great stay at Zarmina’s spacious basement suite. The check-in process was easy, the location was very convenient, and the place was very quiet, clean, and well kept. Zarmina responded to my needs right away, which made the stay even better. The price was also very reasonable for what was offered. I highly recommend this place and would stay again!"
Canada
Akiko M.
The price is NZ$233
includes taxes & fees
6 July - 7 July
Cozy & modern apartment in Pickering

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
Pickering
9.2 out of 10, Wonderful, (5 reviews)
"I had a wonderful stay! The place was clean, cozy, and exactly what I needed. The host was welcoming and made everything easy. I’d definitely recommend it and would love to come back again!"
Canada
Nyajah H.
The price is NZ$615
includes taxes & fees
6 July - 7 July
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

Spacious 4-bedroom house in Pickering

Spacious 4-bedroom house in Pickering
Pickering
7.6 out of 10, Good, (4 reviews)
"Perfect and quiet location for us, plenty of room, clean and comfortable. "
United States
Jacob M.
The price is NZ$841
includes taxes & fees
6 July - 7 July
Spacious 4-bedroom house in Pickering

Airy Nest - 4 Beds, 2.5 Baths, 2 park

Airy Nest - 4 Beds, 2.5 Baths, 2 park
Pickering
The price is NZ$762
includes taxes & fees
19 July - 20 July
Airy Nest - 4 Beds, 2.5 Baths, 2 park

Cozy Countryside Guesthouse with BBQ & Firepit

Cozy Countryside Guesthouse with BBQ & Firepit
Pickering
6.0 out of 10, (2 reviews)
"It was an alright night away. Place was fairly clean, newer Reno for sure with some smaller kinks to be worked out. No wifi instructions and noises in the morning with occupants of the other side of the house. Neat spot for a little getaway for the night."
Canada
Geoff G.
The price is NZ$249
includes taxes & fees
5 July - 6 July
Cozy Countryside Guesthouse with BBQ & Firepit

Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s

Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s
Pickering
10.0 out of 10, Exceptional, (2 reviews)
"The property is a very quick drive to Frenchman’s Bay and a lovely walk to stores such as the grocery store and Michael’s. The host was helpful when we had questions and an issue with the TV. It was a quiet environment although we did hear the dog barking at times for awhile. The Vrbo was clean and well cared for. Overall I would recommend this Vrbo."
United States
Cheryllynne C.
The price is NZ$248
includes taxes & fees
23 July - 24 July
Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s

BEACH HOUSE : FIRST FLOOR

BEACH HOUSE : FIRST FLOOR
Pickering
The price is NZ$293
includes taxes & fees
28 July - 29 July
BEACH HOUSE : FIRST FLOOR

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!
Pickering
The price is NZ$244
includes taxes & fees
9 July - 10 July
Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!

Residence and Conference Centre – Toronto

Residence and Conference Centre – Toronto
2.5 star property
North York
8.0 out of 10, Very good, (1,325 reviews)
"amazing stay!!"
Canada
alexandra
The price is NZ$125
includes taxes & fees
26 July - 27 July
Residence and Conference Centre – Toronto

Oak House Residence

Oak House Residence
3.0 star property
Downtown Toronto
9.2 out of 10, Wonderful, (121 reviews)
"Super convenient location, very fair price, and the rooms were nice and clean."
Canada
Sarah
The price is NZ$248
includes taxes & fees
7 July - 8 July
Oak House Residence

Residence and Conference Centre – King City

Residence and Conference Centre – King City
2.0 star property
King
8.6 out of 10, Excellent, (580 reviews)
"We enjoyed the staff was pleasant and the place was very clean. Great for a family to stay"
United States
Alberta
The price is NZ$118
includes taxes & fees
6 July - 7 July
Residence and Conference Centre – King City
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

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

Can I find a holiday rental in Pickering?

Yes, there are holiday rentals where you'll be only 5.1 mi (8.1 km) from Toronto Zoo, giving you a secluded option if you'd like a quiet spot to stay. Discover why Pickering is known for its zoo. Make sure you have time to check out the hockey games and coffee shops during your trip.

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

A beautiful Walkout basement: This highly rated holiday home rental in Pickering offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate SH203-Cozy Holiday Home as a favourite home for rent in Pickering.

How many holiday rentals are there in Pickering?

Choose from 64 Expedia holiday rentals in Pickering for a memorable holiday.

What can I see and do in Pickering?

Enjoy the outdoors at Rouge National Urban Park and Lake Ontario, or simply take in cultural attractions like Herongate Barn Theatre and Luke Andrews Wood Sculptures. While in the area, you can also visit popular places such as Toronto Zoo and Scarborough Town Centre.

What are holiday rentals like in Pickering?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pickering. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.