We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Pickering Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Neighborhood

Distance from

5 mi
49 rentals in Pickering.
Chalet Claremont - King’s Room, vacation rental in Pickering
Chalet Claremont - King’s Room, vacation rental in Pickering
Chalet Claremont - King’s Room, vacation rental in Pickering

Chalet Claremont - King’s Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Chalet Claremont - Blues Room, vacation rental in Pickering
Chalet Claremont - Blues Room, vacation rental in Pickering
Chalet Claremont - Blues Room, vacation rental in Pickering

Chalet Claremont - Blues Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Chalet Claremont - Sky Room, vacation rental in Pickering
Chalet Claremont - Sky Room, vacation rental in Pickering
Chalet Claremont - Sky Room, vacation rental in Pickering

Chalet Claremont - Sky Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Chalet Claremont - Terrace Room, vacation rental in Pickering
Chalet Claremont - Terrace Room, vacation rental in Pickering
Chalet Claremont - Terrace Room, vacation rental in Pickering

Chalet Claremont - Terrace Room

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Furnished 2 Bedroom Basement Apartment, vacation rental in Pickering
Furnished 2 Bedroom Basement Apartment, vacation rental in Pickering
Furnished 2 Bedroom Basement Apartment, vacation rental in Pickering

Furnished 2 Bedroom Basement Apartment

Condo/Apartment in Scarborough, West Hill
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Brand New Beach Apt w/ 2 Bedroom & Full Washroom, vacation rental in Pickering
Brand New Beach Apt w/ 2 Bedroom & Full Washroom, vacation rental in Pickering
Brand New Beach Apt w/ 2 Bedroom & Full Washroom, vacation rental in Pickering

Brand New Beach Apt w/ 2 Bedroom & Full Washroom

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Quite | Close to Lake | 30 Min. to Downtown| WIFI, vacation rental in Pickering
Quite | Close to Lake | 30 Min. to Downtown| WIFI, vacation rental in Pickering
Quite | Close to Lake | 30 Min. to Downtown| WIFI, vacation rental in Pickering

Quite | Close to Lake | 30 Min. to Downtown| WIFI

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Family shopping plaza lake 2 kilometers, vacation rental in Pickering
Family shopping plaza lake 2 kilometers, vacation rental in Pickering
Family shopping plaza lake 2 kilometers, vacation rental in Pickering

Family shopping plaza lake 2 kilometers

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury 5 Bedroom Oasis with Pool, vacation rental in Pickering
Luxury 5 Bedroom Oasis with Pool, vacation rental in Pickering
Luxury 5 Bedroom Oasis with Pool, vacation rental in Pickering

Luxury 5 Bedroom Oasis with Pool

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Comfy 2 Bedroom Near The Beach! Frenchmans Bay! Close to HWY!, vacation rental in Pickering
Comfy 2 Bedroom Near The Beach! Frenchmans Bay! Close to HWY!, vacation rental in Pickering
Comfy 2 Bedroom Near The Beach! Frenchmans Bay! Close to HWY!, vacation rental in Pickering

Comfy 2 Bedroom Near The Beach! Frenchmans Bay! Close to HWY!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy 3 Bedroom Bungalow | Prime Location, vacation rental in Pickering
Cozy 3 Bedroom Bungalow | Prime Location, vacation rental in Pickering
Cozy 3 Bedroom Bungalow | Prime Location, vacation rental in Pickering

Cozy 3 Bedroom Bungalow | Prime Location

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stylish 3bdrm, 2bth house with 2 parking House, vacation rental in Pickering
Stylish 3bdrm, 2bth house with 2 parking House, vacation rental in Pickering
Stylish 3bdrm, 2bth house with 2 parking House, vacation rental in Pickering

Stylish 3bdrm, 2bth house with 2 parking House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
By-The-Bay 3 Bed 2 Bath Cottage! - 3 minutes to the beach!, vacation rental in Pickering
By-The-Bay 3 Bed 2 Bath Cottage! - 3 minutes to the beach!, vacation rental in Pickering
By-The-Bay 3 Bed 2 Bath Cottage! - 3 minutes to the beach!, vacation rental in Pickering

By-The-Bay 3 Bed 2 Bath Cottage! - 3 minutes to the beach!

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Brand New Detached Bongalo. 5 minutes from Cobourg Beach, vacation rental in Pickering
Brand New Detached Bongalo. 5 minutes from Cobourg Beach, vacation rental in Pickering
Brand New Detached Bongalo. 5 minutes from Cobourg Beach, vacation rental in Pickering

Brand New Detached Bongalo. 5 minutes from Cobourg Beach

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cosy 3-Bedroom Home in Quiet Cul-de-Sac, vacation rental in Pickering
Cosy 3-Bedroom Home in Quiet Cul-de-Sac, vacation rental in Pickering
Cosy 3-Bedroom Home in Quiet Cul-de-Sac, vacation rental in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Dazzling Modern Home Next to Beach & Go Train Station, vacation rental in Pickering
Dazzling Modern Home Next to Beach & Go Train Station, vacation rental in Pickering
Dazzling Modern Home Next to Beach & Go Train Station, vacation rental in Pickering

Dazzling Modern Home Next to Beach & Go Train Station

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Beautiful, Ideally located luxury entire 4 bedroom + Parking, vacation rental in Pickering
Beautiful, Ideally located luxury entire 4 bedroom + Parking, vacation rental in Pickering
Beautiful, Ideally located luxury entire 4 bedroom + Parking, vacation rental in Pickering

Beautiful, Ideally located luxury entire 4 bedroom + Parking

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Convenient Suite, vacation rental in Pickering
Convenient Suite, vacation rental in Pickering
Convenient Suite, vacation rental in Pickering

Convenient Suite

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Comfort Stay at City of Pickering, vacation rental in Pickering
The Comfort Stay at City of Pickering, vacation rental in Pickering
The Comfort Stay at City of Pickering, vacation rental in Pickering

The Comfort Stay at City of Pickering

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy 3-bedroom Bungalow, vacation rental in Pickering
Cozy 3-bedroom Bungalow, vacation rental in Pickering
Cozy 3-bedroom Bungalow, vacation rental in Pickering

Cozy 3-bedroom Bungalow

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
5 mins to Pubs, beach, waterfront trail and GO station to downtown TO, vacation rental in Pickering
5 mins to Pubs, beach, waterfront trail and GO station to downtown TO, vacation rental in Pickering
5 mins to Pubs, beach, waterfront trail and GO station to downtown TO, vacation rental in Pickering

5 mins to Pubs, beach, waterfront trail and GO station to downtown TO

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Premier NEWLY Built 3BR/2.5B Condo: Modern Luxury!, vacation rental in Pickering
Premier NEWLY Built 3BR/2.5B Condo: Modern Luxury!, vacation rental in Pickering
Premier NEWLY Built 3BR/2.5B Condo: Modern Luxury!, vacation rental in Pickering

Premier NEWLY Built 3BR/2.5B Condo: Modern Luxury!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful 3 Bedroom Home w/Free Parking, Wifi and Laundry, vacation rental in Pickering
Beautiful 3 Bedroom Home w/Free Parking, Wifi and Laundry, vacation rental in Pickering
Beautiful 3 Bedroom Home w/Free Parking, Wifi and Laundry, vacation rental in Pickering

Beautiful 3 Bedroom Home w/Free Parking, Wifi and Laundry

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Entire Modern & Spacious Unit with Free Parking, vacation rental in Pickering
Entire Modern & Spacious Unit with Free Parking, vacation rental in Pickering
Entire Modern & Spacious Unit with Free Parking, vacation rental in Pickering

Entire Modern & Spacious Unit with Free Parking

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cheerful and Spacious 6 Bedroom and 4 Bathroom House, vacation rental in Pickering
Cheerful and Spacious 6 Bedroom and 4 Bathroom House, vacation rental in Pickering
Cheerful and Spacious 6 Bedroom and 4 Bathroom House, vacation rental in Pickering

Cheerful and Spacious 6 Bedroom and 4 Bathroom House

Rental Home
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beachy Bungalow, vacation rental in Pickering
Beachy Bungalow, vacation rental in Pickering
Beachy Bungalow, vacation rental in Pickering

Beachy Bungalow

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Tranquil & Cozy 30 min to Toronto ~ Backyard ~ Free Parking, vacation rental in Pickering
Tranquil & Cozy 30 min to Toronto ~ Backyard ~ Free Parking, vacation rental in Pickering
Tranquil & Cozy 30 min to Toronto ~ Backyard ~ Free Parking, vacation rental in Pickering

Tranquil & Cozy 30 min to Toronto ~ Backyard ~ Free Parking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Luxury Modern Home Next to Beach & Go, vacation rental in Pickering
Luxury Modern Home Next to Beach & Go, vacation rental in Pickering
Luxury Modern Home Next to Beach & Go, vacation rental in Pickering

Luxury Modern Home Next to Beach & Go

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Beautiful Walk Out Basement Apt next to Beach & GO Station, vacation rental in Pickering
Beautiful Walk Out Basement Apt next to Beach & GO Station, vacation rental in Pickering
Beautiful Walk Out Basement Apt next to Beach & GO Station, vacation rental in Pickering

Beautiful Walk Out Basement Apt next to Beach & GO Station

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
2 King Beds, 1 Queen Bed 3 Bedrooms. Luxury Rental, vacation rental in Pickering
2 King Beds, 1 Queen Bed 3 Bedrooms. Luxury Rental, vacation rental in Pickering
2 King Beds, 1 Queen Bed 3 Bedrooms. Luxury Rental, vacation rental in Pickering

2 King Beds, 1 Queen Bed 3 Bedrooms. Luxury Rental

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cottage in the SixSteps Away from Beach Great Fishing Rouge River, vacation rental in Pickering
Cottage in the SixSteps Away from Beach Great Fishing Rouge River, vacation rental in Pickering
Cottage in the SixSteps Away from Beach Great Fishing Rouge River, vacation rental in Pickering

Cottage in the SixSteps Away from Beach Great Fishing Rouge River

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Exquisite private Villa just outside of the city., vacation rental in Pickering
Exquisite private Villa just outside of the city., vacation rental in Pickering
Exquisite private Villa just outside of the city., vacation rental in Pickering

Exquisite private Villa just outside of the city.

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Convenient Vacation Home - Heated Pool, vacation rental in Pickering
Convenient Vacation Home - Heated Pool, vacation rental in Pickering
Convenient Vacation Home - Heated Pool, vacation rental in Pickering

Convenient Vacation Home - Heated Pool

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy 30m to Toronto ~ Backyard-free parking, vacation rental in Pickering
Cozy 30m to Toronto ~ Backyard-free parking, vacation rental in Pickering
Cozy 30m to Toronto ~ Backyard-free parking, vacation rental in Pickering

Cozy 30m to Toronto ~ Backyard-free parking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Dazzling Modern Home Next to Beach & Go Station, vacation rental in Pickering
Dazzling Modern Home Next to Beach & Go Station, vacation rental in Pickering
Dazzling Modern Home Next to Beach & Go Station, vacation rental in Pickering

Dazzling Modern Home Next to Beach & Go Station

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Superhouse for all!, vacation rental in Pickering
Superhouse for all!, vacation rental in Pickering
Superhouse for all!, vacation rental in Pickering

Superhouse for all!

Rental Home
8 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Comfort Stay at Pickering, vacation rental in Pickering
The Comfort Stay at Pickering, vacation rental in Pickering
The Comfort Stay at Pickering, vacation rental in Pickering

The Comfort Stay at Pickering

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful One bedroom basement apartment, vacation rental in Pickering
Beautiful One bedroom basement apartment, vacation rental in Pickering
Beautiful One bedroom basement apartment, vacation rental in Pickering

Beautiful One bedroom basement apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Basement with 2 bedroom., vacation rental in Pickering
Basement with 2 bedroom., vacation rental in Pickering
Basement with 2 bedroom., vacation rental in Pickering

Basement with 2 bedroom.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Toronto 4 Bedrooms Large House Clean Beautiful Private Convenient Location, vacation rental in Pickering
Toronto 4 Bedrooms Large House Clean Beautiful Private Convenient Location, vacation rental in Pickering
Toronto 4 Bedrooms Large House Clean Beautiful Private Convenient Location, vacation rental in Pickering

Toronto 4 Bedrooms Large House Clean Beautiful Private Convenient Location

Rental Home in Scarborough, Morningside
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Big Bsmt Unit w own entrance 2 Beds/1W sleeps 4-6, vacation rental in Pickering
Big Bsmt Unit w own entrance 2 Beds/1W sleeps 4-6, vacation rental in Pickering
Big Bsmt Unit w own entrance 2 Beds/1W sleeps 4-6, vacation rental in Pickering

Big Bsmt Unit w own entrance 2 Beds/1W sleeps 4-6

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Your Warm Abode at Prime Highbush Area w/ Backyard, vacation rental in Pickering
Your Warm Abode at Prime Highbush Area w/ Backyard, vacation rental in Pickering
Your Warm Abode at Prime Highbush Area w/ Backyard, vacation rental in Pickering

Your Warm Abode at Prime Highbush Area w/ Backyard

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
New high end finishing apartment, vacation rental in Pickering
New high end finishing apartment, vacation rental in Pickering
New high end finishing apartment, vacation rental in Pickering

New high end finishing apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 28
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 Bedroom plus Office Executive Bungalow in West Rouge, vacation rental in Pickering
2 Bedroom plus Office Executive Bungalow in West Rouge, vacation rental in Pickering
2 Bedroom plus Office Executive Bungalow in West Rouge, vacation rental in Pickering

2 Bedroom plus Office Executive Bungalow in West Rouge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Luxury 1-bedroom 1-parking downtown Pickering, vacation rental in Pickering
Luxury 1-bedroom 1-parking downtown Pickering, vacation rental in Pickering
Luxury 1-bedroom 1-parking downtown Pickering, vacation rental in Pickering

Luxury 1-bedroom 1-parking downtown Pickering

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious Suite by the Lake, Great Neighbourhood!, vacation rental in Pickering
Spacious Suite by the Lake, Great Neighbourhood!, vacation rental in Pickering
Spacious Suite by the Lake, Great Neighbourhood!, vacation rental in Pickering

Spacious Suite by the Lake, Great Neighbourhood!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Absolutely Stunning Views Of Lake Ontario, vacation rental in Pickering
Absolutely Stunning Views Of Lake Ontario, vacation rental in Pickering
Absolutely Stunning Views Of Lake Ontario, vacation rental in Pickering

Absolutely Stunning Views Of Lake Ontario

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Stunning 2 bedroom suite in Pickering, On, vacation rental in Pickering
Stunning 2 bedroom suite in Pickering, On, vacation rental in Pickering
Stunning 2 bedroom suite in Pickering, On, vacation rental in Pickering

Stunning 2 bedroom suite in Pickering, On

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Vacation Home in Pickering, vacation rental in Pickering
Vacation Home in Pickering, vacation rental in Pickering
Vacation Home in Pickering, vacation rental in Pickering

Vacation Home in Pickering

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Showing results 1-49 of 49
Frequently Asked Questions about Pickering