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

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Our top choices for Pickering holiday 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 £109
includes taxes & fees
22 Sept - 23 Sept
Cozy & modern apartment in Pickering

2. 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, (3 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 £98
includes taxes & fees
22 Sept - 23 Sept
Brand new luxurious basement studio apartment 5 minutes away from Frenchman’s

3. 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 £199
includes taxes & fees
4 Oct - 5 Oct
Ultimate KING & QUEEN,PrivateBalcony, FreeParking, WIFI, Safe, Stylish

4. 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 £102
includes taxes & fees
22 Sept - 23 Sept
Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!

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 £110
includes taxes & fees
17 Oct - 18 Oct
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 £186
includes taxes & fees
2 Oct - 3 Oct
Modern Comforts, Quiet Neighborhood, Free 02 Parking

7. 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 £223
includes taxes & fees
22 Sept - 23 Sept
Chic 2BR Suite Stylish Stay w/ Kitchen + Free Parking

8. 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 £245
includes taxes & fees
22 Sept - 23 Sept
Cozy & Charming Apt For 4 | Quiet & Privacy

9. 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 £201
includes taxes & fees
1 Oct - 2 Oct
A beautiful Walkout basement

10. 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.
The price is £324
includes taxes & fees
24 Sept - 25 Sept
King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

11. 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 £285
includes taxes & fees
22 Sept - 23 Sept
Modern Nest - 4 BR House, 5 Beds, 2.5 Baths, 3 Park

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 £300
includes taxes & fees
28 Sept - 29 Sept
Cedar Nest - 5 Beds, 3.5 Baths, 2 Park, Backyard

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

Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard
Lamoreaux
The price is £277
includes taxes & fees
27 Sept - 28 Sept
Soleil Nest - 5 Beds, 2.5 Baths, 2 Park, Backyard

14. 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 £111
includes taxes & fees
22 Sept - 23 Sept
Cozy Countryside Guesthouse with BBQ & Firepit

15. 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 £318
includes taxes & fees
28 Sept - 29 Sept
Spacious 4-bedroom house in Pickering

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

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)
Lamoreaux
7.8 out of 10, Good, (8 reviews)
"We had an amazing stay here, would definitely recommend!"
Canada
Aqsa
The price is £246
includes taxes & fees
23 Sept - 24 Sept
Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

17. 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 £307
includes taxes & fees
28 Sept - 29 Sept
Airy Nest - 4 Beds, 2.5 Baths, 2 park

18. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE
Pickering
The price is £205
includes taxes & fees
22 Sept - 23 Sept
LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

19. 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 £600
includes taxes & fees
22 Sept - 23 Sept
The EastSide Manor - Fully Equipped Mansion, Games Room, Free Parking and More

20. Modern Comforts, Quiet Neighborhood, free 02 parking

Modern Comforts, Quiet Neighborhood, free 02 parking
Liverpool
The price is £189
includes taxes & fees
2 Oct - 3 Oct
Modern Comforts, Quiet Neighborhood, free 02 parking
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 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, apart-hotels, 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 favorite 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 depends 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 £136 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 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. 

Explore a world of travel with Expedia

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?

Entire Private Suite! Free Parking! Comfortable Stay! Excellent Location!: This highly rated holiday home rental in Pickering 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 holiday rentals are there in Pickering?

Choose from 68 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.