229+ Vacation Rentals & Holiday Homes in Pickering |
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Pickering Accommodations - Hotels & Rentals

About Pickering Vacation Rentals

Discover More than 229 Incredible Getaway Rentals Available in Pickering. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Pickering.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Pickering, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Pickering. The Average Size of Places to Stay Near Pickering is 461.43 ft², with Prices Averaging US $192 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Pickering. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Pickering

Type Count
Vacation Homes 158
Holiday Apartments 48
Villas 6

Use these Quick Filters to Find a Vacation Rental in Pickering

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Pickering with Online Reservations.

Weather in Pickering, ON

View the weather forecast for Pickering before booking your Pickering Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Activities PickeringGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World PickeringGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Herongate Barn Theatre
Deer Creek North Golf Course
Glen Cedars Golf Club
Luke Andrews Wood Sculptures
AnNonedale Golf and Country Club
CN Tower
Toronto Eaton Centre
Canada's Wonderland
Rogers Centre
Scotiabank Arena
Ripley's Aquarium of Canada
Metro Toronto Convention Centre
Royal Ontario Museum
Toronto Zoo
Casa Loma
Vaughan Mills Mall
University of Toronto - St. George Campus
Royal Alexandra Theatre
Hockey Hall of Fame
Harbourfront Centre

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Luke Andrews Wood Sculptures 680 Properties
Annandale Golf and Country Club 221 Properties
Glen Cedars Golf Club 105 Properties
Deer Creek North Golf Course 32 Properties
Herongate Barn Theatre 28 Properties

Frequently Asked Questions About Pickering?

What are the top hotels, lake houses & vacation rentals in Pickering?

We provide an array of great vacation destinations in Pickering. If you are looking to stay in or around the Pickering area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Pickering:

Which hotel, lake house, or vacation rental in Pickering is best for families?

Searching for a family-friendly getaway in Pickering? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Pickering?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 229 in the Pickering area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Pickering.

Nearby Neighborhood (1) 
Neighborhood Property Count
Scarborough Vacation Rentals in Oshawa, Ontario 247

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