Pickering Vacation Rentals from ￥20,783: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Pickering vacation rentals

A dining area with a long table, six chairs, a rug, and two paintings on the walls.

1. Cozy & modern apartment in Pickering

Village East

fayssal b.

￥20,994 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Liverpool

Lisa S.

￥16,694 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a stone facade, a front porch, and a garage.

3. BEACH HOUSE : FIRST FLOOR

Bay Ridges

Lloyd K.

￥23,650 total

includes taxes & fees

Nov 22 - Nov 23

A modern high-rise building with multiple balconies and large windows.

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

City Centre

Lisa S.

￥39,523 total

includes taxes & fees

Nov 25 - Nov 26

A modern interior with a wooden panel wall, a black metal gate, and a staircase.

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

Liverpool

Cheryllynne C.

￥22,512 total

includes taxes & fees

Nov 17 - Nov 18

A modern kitchen with white cabinets, a stainless steel sink, a coffee maker, a microwave, and an oven.

6. Newly Renovated, Family Friendly 2-Bedroom Retreat

Liverpool

￥24,282 total

includes taxes & fees

Nov 16 - Nov 17

A spacious foyer with a grand staircase, a glass door leading to a laundry area, and a view through a large window.

7. Modern Comforts, Quiet Neighborhood, Free 02 Parking

Liverpool

Prem

￥35,377 total

includes taxes & fees

Nov 19 - Nov 20

A two-story house with a stone facade, a garage, and a front porch.

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

Highbush

Branden T.

￥43,784 total

includes taxes & fees

Nov 16 - Nov 17

A narrow pathway leading to a wooden gate with a decorative metal plate, flanked by a brick wall and a wooden fence.

9. A beautiful Walkout basement

Highbush

Lance C.

￥40,230 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a stone facade, a balcony, and a garage.

10. King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

Pickering

Steven F.

￥57,553 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a large window, a bed, a nightstand, and a painting on the wall.

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

Lamoreaux

￥60,959 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a sofa, a dining table with chairs, a TV mounted on the wall, and a kitchen in the background.

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

West Shore

"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...

Suzette M.

￥48,058 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a sectional sofa, a small round table, and a large window offering a view of neighboring houses.

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

Lamoreaux

Aqsa

￥48,691 total

includes taxes & fees

Nov 16 - Nov 17

A modern kitchen with a large island, bar stools, and a dining area with a view of the outdoors.

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

Lamoreaux

Jacky P.

￥58,973 total

includes taxes & fees

Nov 16 - Nov 17

A modern living room with a sofa, coffee table, and dining area.

15. Spacious 4-bedroom house in Pickering

Pickering

Jacob M.

￥60,326 total

includes taxes & fees

Nov 23 - Nov 24

A hallway with a cityscape painting, a console table with books, a door, and a coat rack.

16. Cozy Countryside Guesthouse with BBQ & Firepit

Pickering

Geoff G.

￥21,310 total

includes taxes & fees

Nov 16 - Nov 17

A dark wooden door with a small window above it, flanked by two flower planters.

17. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

Pickering

￥39,206 total

includes taxes & fees

Nov 16 - Nov 17

18. Modern Comforts, Quiet Neighborhood, free 02 parking

Liverpool

￥40,158 total

includes taxes & fees

Nov 19 - Nov 20

19. New Modern Home + Free Parking In Ajax

Ajax

Leanne A.

￥37,814 total

includes taxes & fees

Nov 16 - Nov 17

A residential building with a garage, a tree in the front yard, and a car parked in the driveway.

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

Ajax

Rebecca

￥20,994 total

includes taxes & fees

Nov 17 - Nov 18

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Pickering Hotel Reviews

Radisson Blu Toronto Downtown

8/10 Good

"I loved the location of the hotel it was a central place for our tours. The staff was very helpful in helping us decide where to eat. The rooms were a bit small and I think having bedside drawers would help. Otherwise it was a good stay. Breakfast upstairs was great on our 2nd day. Will definitely stay there again."

Pickering Casino Resort Hotel

8/10 Good

"Arrived with international luggage. The check-in set up is inconvenient for parking and transporting luggage to your room. There was a lovely girl who helped me get my bags to my room. The reception staff have a lot to learn from her. She was so welcoming and lovely. The reception staff were not friendly which didn’t make me feel welcome. There was one very kind lady who helped me find somewhere to eat within the casino. The room was perfect, everything I needed. Comfortable bed and pillows. Black out curtains and minimal noise."

TOOR Hotel Toronto, part of JdV by Hyatt

10/10 Excellent

"The room was modern, and exceptionally clean. There was a little noise from outside, but it was quite tolerable. What truly made the difference, however, was the staff. Everyone I encountered was absolutely wonderful, welcoming, and genuinely attentive. They went out of their way to make sure my visit was comfortable and enjoyable. Thank you."

Find out more about Pickering

Search for holiday rentals in Pickering on Expedia! You can easily find your home rentals, villas, holiday apartments in Pickering using one of the methods below:

View our selection of featured holiday rentals in Pickering
Use the map to find apartments and other holiday homes in the Pickering neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Pickering while they last

Look no further and take a look at our great range of rental properties in Pickering!

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 72 Expedia vacation rentals in Pickering for a memorable vacation.

What can I see and do in Pickering?

Rouge National Urban Park and Lake Ontario are a couple of scenic spots to enjoy the outdoors, whereas Luke Andrews Wood Sculptures is one of the cultural attractions. 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Pickering vacation rentals

1. Cozy & modern apartment in Pickering

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

3. BEACH HOUSE : FIRST FLOOR

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

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

6. Newly Renovated, Family Friendly 2-Bedroom Retreat

7. Modern Comforts, Quiet Neighborhood, Free 02 Parking

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

9. A beautiful Walkout basement

10. King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg

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

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

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

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

15. Spacious 4-bedroom house in Pickering

16. Cozy Countryside Guesthouse with BBQ & Firepit

17. LUXE LIVING - PRIVATE COUNTRYSIDE GUESTHOUSE

18. Modern Comforts, Quiet Neighborhood, free 02 parking

19. New Modern Home + Free Parking In Ajax

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

Find vacation rentals that suit your style

Top Pickering Hotel Reviews

Radisson Blu Toronto Downtown

The Omni King Edward Hotel

Pickering Casino Resort Hotel

TOOR Hotel Toronto, part of JdV by Hyatt

Holiday Inn Toronto Downtown Centre by IHG

Cambridge Suites Toronto

Crowne Plaza Toronto North York by IHG

Hyatt Regency Toronto

Find out more about Pickering

Frequently asked questions

Go further with the Expedia app