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

Pickering Holiday Rentals

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Check prices for these dates

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

Our top choices for Pickering holiday rentals

Dining

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 AU$367
includes taxes & fees
14 Sept - 15 Sept
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 AU$206
includes taxes & fees
27 Aug - 28 Aug
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 AU$183
includes taxes & fees
21 Sept - 22 Sept
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 AU$227
includes taxes & fees
2 Sept - 3 Sept
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 AU$203
includes taxes & fees
8 Sept - 9 Sept
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 AU$451
includes taxes & fees
27 Aug - 28 Aug
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)
"Beautiful and clean home & host communicates really well and was very helpful. Would come again!"
United States
Bry G.
The price is AU$521
includes taxes & fees
31 Aug - 1 Sept
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 AU$405
includes taxes & fees
9 Sept - 10 Sept
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 AU$410
includes taxes & fees
27 Aug - 28 Aug
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 AU$558
includes taxes & fees
7 Sept - 8 Sept
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 AU$674
includes taxes & fees
1 Sept - 2 Sept
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 AU$535
includes taxes & fees
6 Sept - 7 Sept
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 AU$558
includes taxes & fees
7 Sept - 8 Sept
Airy Nest - 4 Beds, 2.5 Baths, 2 park
4 bedrooms, desk, iron/ironing board, free WiFi

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 AU$558
includes taxes & fees
7 Sept - 8 Sept
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 AU$524
includes taxes & fees
8 Sept - 9 Sept
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
1 bedroom, desk, free WiFi, 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 AU$206
includes taxes & fees
30 Aug - 31 Aug
Cozy Countryside Guesthouse with BBQ & Firepit
Living area

17. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
Pickering
The price is AU$376
includes taxes & fees
27 Aug - 28 Aug
LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
1 bedroom, desk, free WiFi, 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 AU$181
includes taxes & fees
31 Aug - 1 Sept
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, (10 reviews)
"It was good experience."
Canada
Tulashi
The price is AU$223
includes taxes & fees
30 Aug - 31 Aug
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 AU$358
includes taxes & fees
27 Aug - 28 Aug
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

Sheraton Centre Toronto Hotel

Sheraton Centre Toronto Hotel

10/10 Excellent
"We really enjoyed our stay. I would recommend it to anyone."
Cynthia 2-night trip
Posted less than an hour ago
Sheraton Centre Toronto Hotel

Find out more about Pickering

Everything you need to know about Pickering holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pickering holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Pickering holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pickering holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pickering holiday rentals we have selected for you start as low as AU$192 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Pickering rentals

At Expedia, we put the best Pickering holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Pickering?

Yes, there are holiday rentals in Pickering close to 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 coffee shops during your trip.

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

A beautiful Walkout basement: This highly rated holiday home rental in Pickering offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location! as a favourite home for rent in Pickering.

How many holiday rentals are there in Pickering?

Choose from 63 Expedia holiday rentals in Pickering for a memorable holiday.

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 holiday rentals like in Pickering?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pickering. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family trip.