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

Pickering Vacation Rentals

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Our top choices for Pickering vacation rentals

1. Cozy & modern apartment in Pickering

Cozy & modern apartment in Pickering
Village East
8.8 out of 10, Excellent, (8 reviews)
"Clean and spacious "
Canada
Nouman
The price is CA $98
CA $199 total
includes taxes & fees
Sep 21 - Sep 22
Cozy & modern apartment in Pickering

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

Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish
City Centre
9.0 out of 10, Wonderful, (8 reviews)
"very nice place. easy access to GOtrain"
Canada
Guy
The price is CA $198
CA $363 total
includes taxes & fees
Sep 24 - Sep 25
Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish

3. 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, (3 reviews)
"Was what we needed for the night"
United States
Lisa S.
The price is CA $158
CA $227 total
includes taxes & fees
Sep 23 - Sep 24
Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!

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

Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s
Liverpool
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 CA $105
CA $172 total
includes taxes & fees
Sep 21 - Sep 22
Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s

5. 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 CA $99
CA $223 total
includes taxes & fees
Sep 23 - Sep 24
BEACH HOUSE : FIRST FLOOR

6. Modern Comforts, Quiet Neighborhood, Free 02 Parking

Modern Comforts, Quiet Neighborhood, Free 02 Parking
2.0 star property
Liverpool
The price is CA $294
CA $382 total
includes taxes & fees
Oct 5 - Oct 6
Modern Comforts, Quiet Neighborhood, Free 02 Parking

7. 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 CA $135
CA $367 total
includes taxes & fees
Oct 1 - Oct 2
A beautiful Walkout basement

8. Chic 2BR Suite Stylish Stay w/ Kitchen + Free Parking

Chic 2BR Suite Stylish Stay w/ Kitchen + Free Parking
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 CA $143
CA $408 total
includes taxes & fees
Sep 21 - Sep 22
Chic 2BR Suite Stylish Stay w/ Kitchen + Free Parking

9. Cozy & Charming Apt For 4 | Quiet & Privacy

Cozy & Charming Apt For 4 | Quiet & Privacy
West Shore
8.8 out of 10, Excellent, (3 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 CA $250
CA $424 total
includes taxes & fees
Sep 17 - Sep 18
Cozy & Charming Apt For 4 | Quiet & Privacy

10. 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
9.6 out of 10, Exceptional, (10 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 CA $279
CA $552 total
includes taxes & fees
Sep 21 - Sep 22
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park

11. 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 CA $122
CA $202 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Countryside Guesthouse with BBQ & Firepit

12. 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 CA $294
CA $571 total
includes taxes & fees
Sep 21 - Sep 22
Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard

13. 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 CA $261
CA $473 total
includes taxes & fees
Sep 17 - Sep 18
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

14. 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 CA $294
CA $571 total
includes taxes & fees
Sep 21 - Sep 22
Airy Nest - 4 Beds, 2.5 Baths, 2 park

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

Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard
Lamoreaux
The price is CA $265
CA $546 total
includes taxes & fees
Sep 20 - Sep 21
Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard

16. Spacious 4-bedroom house in Pickering

Spacious 4-bedroom house in Pickering
Pickering
7.2 out of 10, Good, (5 reviews)
"Perfect and quiet location for us, plenty of room, clean and comfortable. "
United States
Jacob M.
The price is CA $221
CA $603 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 4-bedroom house in Pickering

17. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
Pickering
The price is CA $243
CA $354 total
includes taxes & fees
Sep 17 - Sep 18
LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

18. The EastSide Manor - Fully Equipped Mansion, Games Room, Free Parking and More

The EastSide Manor - Fully Equipped Mansion, Games Room, Free Parking and More
Liverpool
The price is CA $878
CA $1,062 total
includes taxes & fees
Sep 17 - Sep 18
The EastSide Manor - Fully Equipped Mansion, Games Room, Free Parking and More

19. Modern Comforts, Quiet Neighborhood, free 02 parking

Modern Comforts, Quiet Neighborhood, free 02 parking
Liverpool
The price is CA $221
CA $350 total
includes taxes & fees
Oct 2 - Oct 3
Modern Comforts, Quiet Neighborhood, free 02 parking

20. 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, (17 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 CA $128
CA $188 total
includes taxes & fees
Oct 1 - Oct 2
Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything
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

Everything you need to know about Pickering vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pickering vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pickering vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pickering vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pickering. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pickering vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pickering vacation rentals we have selected for you start as low as CA $329 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pickering rentals

At Expedia, we put the best Pickering vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pickering rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pickering vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pickering. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Pickering?

Yes, we offer vacation rentals in Pickering near Chestnut Hill Developments Recreation Complex, or you can select a more secluded 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?

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!: Visitors like this Pickering vacation home rental. It is located near the beach and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

How many vacation rentals are there in Pickering?

Choose from 68 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.