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Our top choices for Pickering vacation homes

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
$162 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
The Comfort Stay at City of Pickering Rm A / Free Wi-Fi

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.
$129 nightly
The price is $146
Dec 28 - Dec 29
Total with taxes and fees
Cozy Countryside Guesthouse with BBQ & Firepit

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.
$303 nightly
The price is $342
Jan 12 - Jan 13, 2026
Total with taxes and fees
A beautiful Walkout basement

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, (17)
"Very nice home and setup with guests in mind. Absolutely recommend "
Canada
Jake A.
$273 nightly
The price is $309
Dec 30 - Dec 31
Total with taxes and fees
Furnished Family Home ★ KING BED ★ Parking ★ BBQ ★ Backyard ★ Discounted Price

SHB01-Cozy Holiday Home

SHB01-Cozy Holiday Home
Pickering
$91 nightly
The price is $102
Dec 28 - Dec 29
Total with taxes and fees
SHB01-Cozy Holiday Home

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

Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free
Pickering
$213 nightly
The price is $241
Dec 24 - Dec 25
Total with taxes and fees
Private 2 bedroom Unit, Private entry, 2 parking- pet/smoke free

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, (26)
"It was great! "
Canada
Andrew D.
$345 nightly
The price is $390
Jan 19 - Jan 20, 2026
Total with taxes and fees
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

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.
$291 nightly
The price is $328
Jan 11 - Jan 12, 2026
Total with taxes and fees
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

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
$329 nightly
The price is $372
Jan 4 - Jan 5, 2026
Total with taxes and fees
Ravine Retreat | Chef Kitchen | Toronto Zoo | 20 min to Therma SPA | Entire Home

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.
$462 nightly
The price is $522
Jan 1 - Jan 2, 2026
Total with taxes and fees
Newly built stunning 4-bedroom detached 2-storey home in Pickering.

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)
"Was very close to our destinations for the weekend. Quiet and very nice. Single bed was a little firm but all in all a great stay. "
Canada
Jason
$117 nightly
The price is $132
Jan 8 - Jan 9, 2026
Total with taxes and fees
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

Together Time Getaway, Just 5 Mins to Hwy 401

Together Time Getaway, Just 5 Mins to Hwy 401
Courtice
10.0 out of 10, Exceptional, (1)
"Was super clean, and fully equipped with everything we needed. Fits description and photos to a tee. Host was very helpful and easy to get in contact with if we needed to. Even left a thank you gift for us at the end of our stay. Not a bad thing to say. "
Canada
Kiana
$94 nightly
The price is $106
Jan 17 - Jan 18, 2026
Total with taxes and fees
Together Time Getaway, Just 5 Mins to Hwy 401

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.
$130 nightly
The price is $147
Dec 28 - Dec 29
Total with taxes and fees
Entire 1 bedroom basement suite with separate entrance in North Oshawa

Whitby Gateway - 2BR 3BD 2WR Kitchen Laundry

Whitby Gateway - 2BR 3BD 2WR Kitchen Laundry
Whitby
9.0 out of 10, Wonderful, (2)
"Comfortable stay. Unit was very quiet. Area is new so lots of construction close by. With the AC running in the rest of the house (most of the day) it made the unit cold. There was no way to control the temperature in the unit. Would have been great to have a side table with a lamp in the bedroom I slept in. Gravel walkway at the side of the house to access the unit. Need to be careful walking on the loose gravel. Overall stay was excellent. "
Canada
Oral
$171 nightly
The price is $193
Dec 28 - Dec 29
Total with taxes and fees
Whitby Gateway - 2BR 3BD 2WR Kitchen Laundry

2B Basement | 20% OFF | 0 Cleaning Fee | Mins to Lake | Free Parking

2B Basement | 20% OFF | 0 Cleaning Fee | Mins to Lake | Free Parking
Richmond Hill
9.4 out of 10, Exceptional, (14)
"Cozy stay perfect for teens attending sports competition."
Canada
Etienne G.
$100 nightly
The price is $113
Dec 24 - Dec 25
Total with taxes and fees
2B Basement | 20% OFF | 0 Cleaning Fee | Mins to Lake | Free Parking

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.
$70 nightly
The price is $79
Jan 8 - Jan 9, 2026
Total with taxes and fees
Private bedroom suite in shared house near Ontario Tech U in North Oshawa

The Cozy Home. Lovely 3 bedroom house near Restaurants, Park, Supermarket & 401"

The Cozy Home. Lovely 3 bedroom house near Restaurants, Park, Supermarket & 401"
Vanier
10.0 out of 10, Exceptional, (4)
"Lovely properly. Host was friendly and very helpful. Be happy to stay here again."
United Kingdom
Robert E.
$209 nightly
The price is $237
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Cozy Home. Lovely 3 bedroom house near Restaurants, Park, Supermarket & 401"

DT Retreat : Firepit, Backyard, Arcade

DT Retreat : Firepit, Backyard, Arcade
Bowmanville
10.0 out of 10, Exceptional, (2)
"Our family really enjoyed our stay. Lovely home, extremely clean, with lots to do. The hosts were incredibly responsive for any question and made us feel at home. Great option for a family staying in the area. "
Canada
Rishia
$251 nightly
The price is $284
Jan 7 - Jan 8, 2026
Total with taxes and fees
DT Retreat : Firepit, Backyard, Arcade

A Modern Private Basement Suite – Richmond Hill

A Modern Private Basement Suite – Richmond Hill
Richmond Hill
9.2 out of 10, Wonderful, (5)
"Had an incredible stay. Communication was great, they were very understanding that we were at Canadas Wonderland for the day and would be checking in late. Everything was exactly like they had advertised. Would definitely recommend. "
United States
Cheyenne C.
$142 nightly
The price is $161
Dec 25 - Dec 26
Total with taxes and fees
A Modern Private Basement Suite – Richmond Hill

Charming bungalow in lovely Richmond Hill with AC, WiFi

Charming bungalow in lovely Richmond Hill with AC, WiFi
Richmond Hill
8.2 out of 10, Very Good, (10)
"Highly recommend, will come again"
Canada
Aileen
$129 nightly
The price is $146
Jan 6 - Jan 7, 2026
Total with taxes and fees
Charming bungalow in lovely Richmond Hill with AC, WiFi
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

Pickering Vacation Homes information

Number of reviews
108
Accommodation
917 Vacation Homes
Lowest Price
$79
Highest Price
$520

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