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Pickering Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Pickering vacation rentals

1 bedroom, WiFi, bed sheets
SHB01-Cozy Holiday Home

SHB01-Cozy Holiday Home

SHB01-Cozy Holiday Home
Pickering
The price is ￥5,925
￥15,965 total
includes taxes & fees
Jan 16 - Jan 17, 2026
SHB01-Cozy Holiday Home
Terrace/patio
VRBO HUGE KING BED , PRIVATE BALCONY, LAKE VIEWS, next 2 GO & Pickering Casino

VRBO HUGE KING BED , PRIVATE BALCONY, LAKE VIEWS, next 2 GO & Pickering Casino

VRBO HUGE KING BED , PRIVATE BALCONY, LAKE VIEWS, next 2 GO & Pickering Casino
2.0 star property
Pickering
8.0 out of 10, Very Good, (1)
"The facilities and apartment are lovely, nicely decorated and comfortable."
Canada
Barb B.
The price is ￥15,951
￥31,672 total
includes taxes & fees
Jan 9 - Jan 10, 2026
VRBO HUGE KING BED , PRIVATE BALCONY, LAKE VIEWS, next 2 GO & Pickering Casino
Exterior detail
A beautiful Walkout basement

A beautiful Walkout basement

A beautiful Walkout basement
Pickering
10.0 out of 10, Exceptional, (1)
"Great place and quiet neighborhood. "
United States
Lance C.
The price is ￥18,982
￥54,024 total
includes taxes & fees
Jan 13 - Jan 14, 2026
A beautiful Walkout basement
Outdoor dining
Ultimate Hideway, Private Balcony, next to train for Fast access to downtown TO

Ultimate Hideway, Private Balcony, next to train for Fast access to downtown TO

Ultimate Hideway, Private Balcony, next to train for Fast access to downtown TO
2.0 star property
Pickering
The price is ￥13,673
￥30,257 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ultimate Hideway, Private Balcony, next to train for Fast access to downtown TO
Interior
The Comfort Stay at City of Pickering Rm A / Free Wi-Fi

The Comfort Stay at City of Pickering Rm A / Free Wi-Fi

The Comfort Stay at City of Pickering Rm A / Free Wi-Fi
Pickering
The price is ￥11,793
￥28,519 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The Comfort Stay at City of Pickering Rm A / Free Wi-Fi
Paper towels
Cozy Entire Apartment - Quiet & Privacy

Cozy Entire Apartment - Quiet & Privacy

Cozy Entire Apartment - Quiet & Privacy
Pickering
8.0 out of 10, Very Good, (2)
"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 ￥22,788
￥43,904 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy Entire Apartment - Quiet & Privacy
Beach
Furnished Family Home ★ KING BED ★ Parking ★ BBQ ★ Backyard ★ Discounted Price

Furnished Family Home ★ KING BED ★ Parking ★ BBQ ★ Backyard ★ Discounted Price

Furnished Family Home ★ KING BED ★ Parking ★ BBQ ★ Backyard ★ Discounted Price
Pickering
8.8 out of 10, Excellent, (18)
"Very nice home and setup with guests in mind. Absolutely recommend "
Canada
Jake A.
Furnished Family Home ★ KING BED ★ Parking ★ BBQ ★ Backyard ★ Discounted Price
Microwave, oven, stovetop, dishwasher
Ravine Retreat | Chef Kitchen | Toronto Zoo | 20 min to Therma SPA | Entire Home

Ravine Retreat | Chef Kitchen | Toronto Zoo | 20 min to Therma SPA | Entire Home

Ravine Retreat | Chef Kitchen | Toronto Zoo | 20 min to Therma SPA | Entire Home
Pickering
The price is ￥19,754
￥58,815 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Ravine Retreat | Chef Kitchen | Toronto Zoo | 20 min to Therma SPA | Entire Home
Outdoor dining
Elegant & Stylish, Beautiful City Views, Private Balcony, Relax & Unwind

Elegant & Stylish, Beautiful City Views, Private Balcony, Relax & Unwind

Elegant & Stylish, Beautiful City Views, Private Balcony, Relax & Unwind
Pickering
The price is ￥20,406
￥37,478 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Elegant & Stylish, Beautiful City Views, Private Balcony, Relax & Unwind
4 bedrooms, desk, iron/ironing board, travel crib
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

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

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
Pickering
10.0 out of 10, Exceptional, (1)
"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 ￥26,454
￥51,892 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
Interior
Cozy Countryside Guesthouse with BBQ & Firepit

Cozy Countryside Guesthouse with BBQ & Firepit

Cozy Countryside Guesthouse with BBQ & Firepit
Pickering
6.0 out of 10, (2)
"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 ￥13,843
￥22,853 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy Countryside Guesthouse with BBQ & Firepit
Interior
Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free

Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free

Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free
Pickering
The price is ￥27,060
￥37,788 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free
Fridge, microwave, oven, stovetop
Newly built stunning 4-bedroom detached 2-storey home in Pickering.

Newly built stunning 4-bedroom detached 2-storey home in Pickering.

Newly built stunning 4-bedroom detached 2-storey home in Pickering.
Pickering
10.0 out of 10, Exceptional, (2)
"Great property. Host was very helpful and place was very nice and clean."
Canada
Ryan J.
The price is ￥57,425
￥82,272 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Newly built stunning 4-bedroom detached 2-storey home in Pickering.
Exterior
Cozy getaway only 1 hr from Toronto, on a small private lake.

Cozy getaway only 1 hr from Toronto, on a small private lake.

Cozy getaway only 1 hr from Toronto, on a small private lake.
Kawartha Lakes
10.0 out of 10, Exceptional, (32)
"Wonderful stay, peaceful retreat "
United States
Sophia c.
The price is ￥13,399
￥18,635 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy getaway only 1 hr from Toronto, on a small private lake.
Interior
Entire 1 bedroom basement suite with separate entrance in North Oshawa

Entire 1 bedroom basement suite with separate entrance in North Oshawa

Entire 1 bedroom basement suite with separate entrance in North Oshawa
Donevan
9.6 out of 10, Exceptional, (7)
"Spacious accommodations. Easy check-in. "
Canada
Paul L.
The price is ￥8,204
￥22,918 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Entire 1 bedroom basement suite with separate entrance in North Oshawa
Dining
Private bedroom suite in shared house near Ontario Tech U in North Oshawa

Private bedroom suite in shared house near Ontario Tech U in North Oshawa

Private bedroom suite in shared house near Ontario Tech U in North Oshawa
2.0 star property
Samac
10.0 out of 10, Exceptional, (3)
"CC’s place was a perfect stay for my trip to Oshawa. Check in was easy, room was spotless and had everything needed to feel at home. Only a 5 minute walk to Durham College, and nearby restaurants. Highly recommend for anyone visiting Oshawa or Durham College"
Canada
Mark M.
The price is ￥7,748
￥16,738 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private bedroom suite in shared house near Ontario Tech U in North Oshawa
Executive View Suite | Terrace/patio
Executive Hotel Cosmopolitan Toronto

Executive Hotel Cosmopolitan Toronto

Executive Hotel Cosmopolitan Toronto
4.0 star property
Downtown Toronto
8.2 out of 10, Very Good, (2220)
"Clean, comfy, great location! "
Canada
Julie
The price is ￥17,063
￥22,176 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Executive Hotel Cosmopolitan Toronto
Banquet hall
One King West Hotel & Residence

One King West Hotel & Residence

One King West Hotel & Residence
4.0 star property
Downtown Toronto
9.2 out of 10, Wonderful, (11873)
"Great place to stay"
Canada
Peter
The price is ￥16,338
￥20,032 total
includes taxes & fees
Jan 4 - Jan 5, 2026
One King West Hotel & Residence
Fridge, microwave, oven, stovetop
One bedroom apartment/suite

One bedroom apartment/suite

One bedroom apartment/suite
Whitby
10.0 out of 10, Exceptional, (21)
"Super clean, comfortable, nice to have the little kitchenette - would stay again for sure!"
Canada
Elizabeth F.
The price is ￥10,824
￥18,282 total
includes taxes & fees
Jan 1 - Jan 2, 2026
One bedroom apartment/suite
Exterior detail
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking
Ajax
9.4 out of 10, Exceptional, (21)
"Clean quite enjoying my stay!"
Canada
Aleashia S.
The price is ￥8,887
￥18,669 total
includes taxes & fees
Jan 4 - Jan 5, 2026
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking
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

Sheraton Centre Toronto Hotel

Sheraton Centre Toronto Hotel

10/10 Excellent
"Great check in experience Room has a great view of Nathan Phillips square at the Richmond tower Grab and go breakfast at dual citizen was fine but overpriced. Pool area is great but lacks a hot tub"
Scott 1-night trip
Posted 11 hours ago
Sheraton Centre Toronto Hotel

Find out more about Pickering

Search for holiday rentals in Pickering on Expedia! You can easily find your home rentals, villas, holiday apartments in Pickering using one of the methods below:

  • View our selection of featured holiday rentals in Pickering
  • Use the map to find apartments and other holiday homes in the Pickering neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pickering while they last

Look no further and take a look at our great range of rental properties in Pickering!

Frequently asked questions

Can I find a vacation rental in Pickering?

Yes, we offer vacation rentals near well known points of interest in Pickering, or you can select a more remote option if you're looking for a relaxing stay. Discover why Pickering is known for its zoo. Make sure you have time to check out the hockey games and coffeehouses during your trip.

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

A beautiful Walkout basement: Visitors like this Pickering vacation home rental. It offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Pickering?

Choose from 65 Expedia vacation rentals in Pickering for a memorable vacation.

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. Pickering Casino Resort and Deer Creek North Golf Course are other places to visit while you're in town.

What are vacation rentals like in Pickering?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Pickering. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.