Pickering Vacation Rentals & Ski-in/Ski-out Homes
House
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $138/Night
7 Nights - US $964
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
150.69 ft²
- Fireplace/Heating
Balcony/Terrace- Parking
- Air Conditioner
US $55/Night
7 Nights - US $383
Apartment
4.8Average
(3 Reviews)
1 Bedroom
1 Bath
Oceanfront- Fireplace/Heating
Ocean View- Balcony/Terrace
US $110/Night
7 Nights - US $773
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1135 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $158/Night
7 Nights - US $1,103
New
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $79/Night
7 Nights - US $550
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $227/Night
7 Nights - US $1,589
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $113/Night
7 Nights - US $794
Apartment
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $131/Night
7 Nights - US $915
House
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $79/Night
7 Nights - US $552
Luxury Places to Stay in Pickering
Over 239+ Luxury Places to Stay in or Near Pickering
Villa
5 Bedrooms
4 Baths
16 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $1,305/Night
7 Nights - US $9,132
House
10.0Exceptional
(1 Review)
5 Bedrooms
6 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $976/Night
7 Nights - US $6,832
House
7.8Very Good
(8 Reviews)
8 Bedrooms
5 Baths
22 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $884/Night
7 Nights - US $6,185
Villa
5.0Average
(1 Review)
5 Bedrooms
5 Baths
14 Guests
2497.23 ft²
Hot Tub- Fireplace/Heating
View- Parking
US $819/Night
7 Nights - US $5,731
New
House
4 Bedrooms
4 Baths
7 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $739/Night
7 Nights - US $5,176
Condo
10.0Exceptional
(2 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $665/Night
7 Nights - US $4,654
House
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $602/Night
7 Nights - US $4,215
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $492/Night
7 Nights - US $3,447
House
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $478/Night
7 Nights - US $3,349
Top-Rated Vacation Rentals with a Pool in Pickering
Over 13+ Top-Rated Vacation Rentals with a Pool in or Near Pickering
Hotel
9.0Exceptional
(4701 Reviews)
1 Bath
Pool
Breakfast- Kitchen
- Parking
US $118/Night
7 Nights - US $824
Resort
8.6Fabulous
(1607 Reviews)
7 Baths
16 Guests
520.97 ft²
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
US $166/Night
7 Nights - US $1,164
Apartment
1 Bedroom
1 Bath
4 Guests
600 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $214/Night
7 Nights - US $1,498
Condo
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
6 Guests
688 ft²
Spa- Fireplace/Heating
- Pool
- Ocean View
US $109/Night
7 Nights - US $763
Villa
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
12 Guests
5000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $3,074/Night
7 Nights - US $21,518
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $122/Night
7 Nights - US $856
Apartment
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $222/Night
7 Nights - US $1,554
House
4.0Average
(5 Reviews)
4 Bedrooms
2 Baths
12 Guests
1600 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $217/Night
7 Nights - US $1,522
Condo
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Parking
US $271/Night
7 Nights - US $1,895
Pet-Friendly Vacation Rentals in Pickering
Over 35+ Pet-Friendly Vacation Rentals in or Near Pickering
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $134/Night
7 Nights - US $937
Villa
9.8Exceptional
(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $168/Night
7 Nights - US $1,173
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $227/Night
7 Nights - US $1,588
Boat Rental
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $122/Night
7 Nights - US $854
House
8.7Fabulous
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
US $86/Night
7 Nights - US $604
House
10.0Exceptional
(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $216/Night
7 Nights - US $1,510
House
9.6Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $156/Night
7 Nights - US $1,094
House
8.8Fabulous
(20 Reviews)
3 Bedrooms
2 Baths
7 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $267/Night
7 Nights - US $1,872
House
8.0Excellent
(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $432/Night
7 Nights - US $3,024
Large Vacation Homes & Villas in Pickering
Over 13+ Large Vacation Homes & Villas in or Near Pickering
House
10.0Exceptional
(1 Review)
6 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $360/Night
7 Nights - US $2,517
Villa
9.3Exceptional
(18 Reviews)
3 Bedrooms
1 Bath
7 Guests
2195.84 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $292/Night
7 Nights - US $2,046
New
House
5 Bedrooms
1 Bath
8 Guests
2500 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $248/Night
7 Nights - US $1,733
House
9.1Exceptional
(22 Reviews)
6 Bedrooms
5 Baths
18 Guests
592.01 ft²
- Fireplace/Heating
- View
- Kitchen
- Parking
US $137/Night
7 Nights - US $962
House
10.0Exceptional
(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $457/Night
7 Nights - US $3,199
House
8.0Excellent
(5 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $163/Night
7 Nights - US $1,138
House
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $760/Night
7 Nights - US $5,322
House
8.0Excellent
(1 Review)
5 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $188/Night
7 Nights - US $1,314
House
4.0Average
(1 Review)
5 Bedrooms
2 Baths
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $89/Night
7 Nights - US $626
Wheelchair Accessible Vacation Homes in Pickering
Over 3+ Wheelchair Accessible Vacation Homes in or Near Pickering
Condo
1 Bedroom
1 Bath
3 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $71/Night
7 Nights - US $499
Condo
1 Bedroom
1 Bath
4 Guests
600 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $209/Night
7 Nights - US $1,463
House
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $68/Night
7 Nights - US $478
Pickering Resorts and Airbnb Homes Under $200
Over 153+ Pickering Resorts and Airbnb Homes Under $200
Apartment
8.6Fabulous
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $62/Night
7 Nights - US $434
Apartment
9.6Exceptional
(23 Reviews)
1 Bedroom
1 Bath
4 Guests
699.65 ft²
- Fireplace/Heating
- View
- Parking
- Air Conditioner
US $54/Night
7 Nights - US $379
House
1 Bedroom
1 Bath
- Internet
- Child Friendly
Bedding/Linens
Designated Smoking Area
US $129/Night
7 Nights - US $902
Apartment
8.4Excellent
(8 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $124/Night
7 Nights - US $871
Apartment
9.4Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
8 Guests
1302.43 ft²
- Balcony/Terrace
- View
- Breakfast
- Parking
US $154/Night
7 Nights - US $1,078
House
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $145/Night
7 Nights - US $1,015
House
6.0Good
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $112/Night
7 Nights - US $787
House
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $116/Night
7 Nights - US $812
House
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $64/Night
7 Nights - US $445
Instantly Bookable Vacation Homes in Pickering
Over 95+ Instantly Bookable Vacation Homes in or Near Pickering
Apartment
8.0Excellent
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $277/Night
7 Nights - US $1,941
Apartment
1 Bedroom
1 Bath
3 Guests
- Air Conditioner
- Child Friendly
Laundry
Security/Safety
US $52/Night
7 Nights - US $364
Bed & Breakfast
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
129 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $137/Night
7 Nights - US $957
House
2.0Average
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $92/Night
7 Nights - US $647
House
2 Bedrooms
1 Bath
6 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $254/Night
7 Nights - US $1,778
New
House
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $207/Night
7 Nights - US $1,451
Apartment
2 Bedrooms
1 Bath
5 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $191/Night
7 Nights - US $1,340
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $191/Night
7 Nights - US $1,339
Apartment
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $138/Night
7 Nights - US $964
Book a Last Minute Place to Stay in Pickering
About Pickering Vacation Rentals
Explore over 248 vacation rentals in Pickering with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Pickering for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Pickering. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Pickering tailored to your preferences. On average, these rentals offer 476.58 ft² of space, and are priced at an average of US $196 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Pickering at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Pickering
| Type | Count |
|---|---|
| Vacation Homes | 167 |
| Holiday Apartments | 59 |
| Villas | 6 |
| B&B | 2 |
| Unique Vacation Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Pickering
★ Pro Tip: Discover Your Ideal Vacation Rental in Pickering with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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
Top Attractions Around Pickering, ON
Sunski offers a large selection of top attractions around Pickering . Research things to do on your vacation before you visit Pickering.
Other Places to Stay in Pickering, ON
Frequently Asked Questions About Pickering?
What are the top vacation rentals in Pickering?
When organizing your trip to Pickering, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Pickering. Peruse our collection of highly-rated properties and secure your reservation today.
- King Bed I Chefs Kitchen I Toronto Hub I 5 Beds 3.5 Bath I 8km from Tesla Chrg
- Cosy 3-Bedroom Home in Quiet Cul-de-Sac
- RedDore - 2 Bedroom Cozy Basement Suite
- Vacation Home in Pickering
- Lakeside Luxe
- Elegant 2-bedroom townhome in Pickering with AC Free Wifi and Parking included
- Lux Style | New Town | Pickering | Greater Toronto
- Spacious Basement Apt Open Concept wth Separate Entrance No Walls Dividing Rooms
- Luxurious Home Away From Home
- Luxury 3 Bedroom Family Home - w/Free WiFi & Parking. 20mins from Downtown
Which vacation homes or resorts in Pickering are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Pickering. Enjoy great views, locations and save money with SunSki Resorts.™
- Getaway Custom Luxurious Home & Affordable Price
- Spacious Basement Lower Suite 3BR Home Stay 1 King 2 Queen Beds 2 Car Parkings FIFA 2026
- Luxurious Rooms in Pickering
How many SunSkiResorts vacation rentals or resorts are available in Pickering?
Discover the ideal vacation rental in Pickering with SunSki Resorts™. We provide an extensive selection of over 248 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Pickering.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Scarborough Vacation Rentals in Oshawa, Ontario | 207 |
People Also Ask
Finding the best prices in Pickering
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