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

Holiday Homes in Pickering

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pickering holiday homes

A modern kitchen with a central island, a wooden cabinet, and a decorative wall piece.

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

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!
Liverpool
10.0 out of 10, Exceptional, (2 reviews)
"Was what we needed for the night"
United States
Lisa S.
The price is NZ$245
includes taxes & fees
1 Sept - 2 Sept
Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!

2. Modern Comforts, Quiet Neighborhood, Free 02 Parking

Modern Comforts, Quiet Neighborhood, Free 02 Parking
2.0 star property
Liverpool
The price is NZ$418
includes taxes & fees
8 Sept - 9 Sept
Modern Comforts, Quiet Neighborhood, Free 02 Parking
A staircase with wooden steps and white trim, leading to a living area with a sofa and a coffee table.

3. BEACH HOUSE : FIRST FLOOR

BEACH HOUSE : FIRST FLOOR
Bay Ridges
8.0 out of 10, Very good, (2 reviews)
"The location was wonderful and Tanika was a great host. House was clean and well organized. Definitely would book with her again!"
United States
Mysty K.
The price is NZ$271
includes taxes & fees
7 Sept - 8 Sept
BEACH HOUSE : FIRST FLOOR
A wooden staircase with a handrail and a balustrade.

4. Beautiful three bedroom house in Pickering

Beautiful three bedroom house in Pickering
Duffin Heights
8.8 out of 10, Excellent, (10 reviews)
"Beautiful and clean home & host communicates really well and was very helpful. Would come again!"
United States
Bry G.
Beautiful three bedroom house in Pickering
A two-story house with a stone facade, a garage, and a front porch.

5. Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard

Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard
Highbush
10.0 out of 10, Exceptional, (2 reviews)
"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$489
includes taxes & fees
1 Sept - 2 Sept
Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard
A modern living room with a marble-patterned rug, a sofa, and a glass coffee table.

6. A beautiful Walkout basement

A beautiful Walkout basement
Highbush
9.6 out of 10, Exceptional, (10 reviews)
"Space was great, clean and a good location"
Canada
Chelsea
The price is NZ$476
includes taxes & fees
7 Sept - 8 Sept
A beautiful Walkout basement
A modern kitchen with a central island, a dining area with a bench, and a living room with a fireplace.

7. 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)
"Great stay, beautiful place "
Canada
Steven F.
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg
A modern kitchen with a large island, bar stools, and a dining area with a view of the outdoors.

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

Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park
Lamoreaux
10.0 out of 10, Exceptional, (8 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$690
includes taxes & fees
7 Sept - 8 Sept
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park
A staircase with wooden railings leading to a room with a bed and a white door.

9. Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard

Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard
Lamoreaux
The price is NZ$659
includes taxes & fees
6 Sept - 7 Sept
Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard
A modern bedroom with a large bed, a desk, and a chair.

10. Cozy Countryside Guesthouse with BBQ & Firepit

Cozy Countryside Guesthouse with BBQ & Firepit
Pickering
7.6 out of 10, Good, (4 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$245
includes taxes & fees
1 Sept - 2 Sept
Cozy Countryside Guesthouse with BBQ & Firepit
A modern living space with a kitchen, dining area, and seating area.

11. Airy Nest - 4 Beds, 2.5 Baths, 2 park

Airy Nest - 4 Beds, 2.5 Baths, 2 park
Lamoreaux
10.0 out of 10, Exceptional, (1 review)
The price is NZ$681
includes taxes & fees
14 Sept - 15 Sept
Airy Nest - 4 Beds, 2.5 Baths, 2 park
A modern living room with a sofa, coffee table, and dining area.

12. 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$811
includes taxes & fees
7 Sept - 8 Sept
Spacious 4-bedroom house in Pickering
A neatly made bed with white linens, a grey towel, and a nightstand with a lamp.

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

Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard
Lamoreaux
10.0 out of 10, Exceptional, (1 review)
The price is NZ$690
includes taxes & fees
7 Sept - 8 Sept
Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard
A modern living room with a grey sofa, a coffee table, and a dining area with a black chair and a small table.

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

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
Lamoreaux
7.6 out of 10, Good, (7 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$576
includes taxes & fees
8 Sept - 9 Sept
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

15. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
Pickering
The price is NZ$449
includes taxes & fees
14 Sept - 15 Sept
LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

16. Modern Comforts, Quiet Neighborhood, free 02 parking

Modern Comforts, Quiet Neighborhood, free 02 parking
Liverpool
Modern Comforts, Quiet Neighborhood, free 02 parking
A modern hotel room with a bed, bedside table, lamp, and a fireplace.

17. Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything
Ajax
10.0 out of 10, Exceptional, (16 reviews)
"We had a great stay at this clean, spacious and convenient property. Highly recommended it for anyone that prefers a larger accommodation over a local hotel."
Canada
Gianclaudio
The price is NZ$210
includes taxes & fees
1 Sept - 2 Sept
Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

18. New Modern Home + Free Parking In Ajax

New Modern Home + Free Parking In Ajax
Ajax
8.8 out of 10, Excellent, (18 reviews)
"Clean, convenient, and easy to check-in and out!"
United States
Jordan
The price is NZ$425
includes taxes & fees
1 Sept - 2 Sept
New Modern Home + Free Parking In Ajax
A dining area with a glass table, four chairs, a refrigerator, and a kitchen in the background.

19. Welcome! This is a private 1-bedroom lower-level basement suite in our home.

Welcome! This is a private 1-bedroom lower-level basement suite in our home.
Ajax
The price is NZ$276
includes taxes & fees
30 Sept - 1 Oct
Welcome! This is a private 1-bedroom lower-level basement suite in our home.

20. Spacious 4BR Family Retreat in Quiet Ajax Suburb

Spacious 4BR Family Retreat in Quiet Ajax Suburb
Ajax
The price is NZ$706
includes taxes & fees
1 Sept - 2 Sept
Spacious 4BR Family Retreat in Quiet Ajax Suburb
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

DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

10/10 Excellent
"This is a great central downtown location that's close to transit and popular spots. The highlight for my daughter and I is the breakfast. The beds are cozy, the views are good, and the staff are stellar. This was our 2nd summer in a row to visit and choose this hotel."
Gwyn 2-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Toronto Downtown

Find out more about Pickering

Pickering Holiday Homes information

Number of reviews
102
Accommodation
681 Holiday Homes
Lowest Price
NZ$210
Highest Price
NZ$811