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

Pickering Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Pickering vacation rentals

1 bedroom, desk, iron/ironing board, travel crib

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

Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish
City Centre
9.0 out of 10, Wonderful, (7 reviews)
"very nice place. easy access to GOtrain"
Canada
Guy
The price is CA $198
CA $364 total
includes taxes & fees
Sep 14 - Sep 15
Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish
Interior

2. 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 CA $135
CA $201 total
includes taxes & fees
Aug 25 - Aug 26
Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!
Interior

3. 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
Interior

4. 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 1 - Sep 2
BEACH HOUSE : FIRST FLOOR
Dining

5. Cozy & modern apartment in Pickering

Cozy & modern apartment in Pickering
Village East
8.4 out of 10, Very good, (5 reviews)
"Clean and spacious "
Canada
Nouman
The price is CA $98
CA $199 total
includes taxes & fees
Sep 8 - Sep 9
Cozy & modern apartment in Pickering
Smart TV

6. 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 $449 total
includes taxes & fees
Aug 25 - Aug 26
Cozy & Charming Apt For 4 | Quiet & Privacy
Interior

7. Beautiful three bedroom house in Pickering

Beautiful three bedroom house in Pickering
Duffin Heights
8.8 out of 10, Excellent, (10 reviews)
"The host was very good at communicating. The property was very welcoming."
United States
Dizahab C.
The price is CA $108
CA $524 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful three bedroom house in Pickering
Interior

8. A beautiful Walkout basement

A beautiful Walkout basement
Highbush
9.6 out of 10, Exceptional, (9 reviews)
"Space was great, clean and a good location"
Canada
Chelsea
The price is CA $162
CA $396 total
includes taxes & fees
Sep 21 - Sep 22
A beautiful Walkout basement
Exterior

9. 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 CA $182
CA $457 total
includes taxes & fees
Sep 1 - Sep 2
Chic 2BR Suite Stylish Stay w/ Kitchen + Backyard
Interior

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
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 CA $279
CA $550 total
includes taxes & fees
Sep 7 - Sep 8
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park
Smart TV, fireplace

11. 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 CA $274
CA $673 total
includes taxes & fees
Aug 27 - Aug 28
Spacious 4-bedroom house in Pickering
Interior

12. 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 $544 total
includes taxes & fees
Sep 6 - Sep 7
Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard
Living area

13. 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 $568 total
includes taxes & fees
Sep 7 - Sep 8
Airy Nest - 4 Beds, 2.5 Baths, 2 park
4 bedrooms, desk, iron/ironing board, WiFi (free)

14. 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 $568 total
includes taxes & fees
Sep 7 - Sep 8
Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard
Smart TV

15. 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 $292
CA $542 total
includes taxes & fees
Sep 8 - Sep 9
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
1 bedroom, desk, WiFi (free), bed sheets

16. 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
Aug 25 - Aug 26
Cozy Countryside Guesthouse with BBQ & Firepit
Living area

17. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
Pickering
The price is CA $243
CA $374 total
includes taxes & fees
Aug 25 - Aug 26
LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
1 bedroom, desk, WiFi (free), bed sheets

18. 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 CA $107
CA $164 total
includes taxes & fees
Aug 26 - Aug 27
Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything
Smart TV

19. Cozy Suite-Close to Pickering Casino Resort, dog parks, and waterfront Trail

Cozy Suite-Close to Pickering Casino Resort, dog parks, and waterfront Trail
Ajax
10.0 out of 10, Exceptional, (9 reviews)
"My stay was amazing as always...This is the best VRBO to stay at whenever I'm traveling to Toronto.The owner is an amazing person and always accommodating!!!"
United States
William D.
The price is CA $77
CA $208 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Suite-Close to Pickering Casino Resort, dog parks, and waterfront Trail
Private kitchen

20. 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 CA $175
CA $349 total
includes taxes & fees
Aug 25 - Aug 26
New Modern Home + Free Parking In Ajax
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

Toronto Don Valley Hotel and Suites

Toronto Don Valley Hotel and Suites

8/10 Good
"This is overall a nice hotel when you can find a good price on the rooms. It was the most affordable hotel in Toronto so I took the chance and Ubered where I needed to be from there. It is worth the stay but had a few issues. I’m in a long distance relationship and have been using hotels a lot to have somewhere to stay when my partner visits so I bring a laptop to connect to the hotel tv’s. Disappointed that the tv’s at this hotel are old and low quality because the hdmi input was so in the back of it that I almost couldn’t plug in my laptop to watch programming I’d actually watch in a hotel. I hope they upgrade the tv’s or get streaming capabilities because no one likes to watch basic cable anymore. Thankfully I figured the tv out though. Also there aren’t any microwaves which made me sad since I usually like to bring popcorn as a snack. The wifi did mostly work but it did keep cutting out more often than other hotels. I understand it’s a big hotel but it is something customers nowadays really care about so I hope the hotel takes this into account. I’m also not sure how maintenance does things because we didn’t get our towels or sheets replaced at any point or asked to do so. It is a decent place overall though. The room was fairly standard but had a bit of extra room which was nice."
Kara 3-night trip
Posted 3 hours ago
Toronto Don Valley Hotel and Suites

Find out more about Pickering

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

A beautiful Walkout basement: Visitors give good reviews to this Pickering vacation home rental, which 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. Our travelers also rate Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location! as a favorite home for rent in Pickering.

How many vacation rentals are there in Pickering?

Choose from 64 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. While in the area, you can also visit popular places like Toronto Zoo and Scarborough Town Centre.

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.