
Holiday rentals in Pickering
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Top-rated holiday rentals in Pickering
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Pickering

Home in Pickering
5 out of 5 average rating, 3 reviewsHome away from Home
TeresaRating, 5 stars2 weeks ago
My friends and I loved staying with Jonny the place was spotless and there was plenty of space for everyone. Jonny was also very accommodating and responsive. Will definitely book with him again.
Top guest favourite

Home in Pickering
5 out of 5 average rating, 11 reviews"Suite Escape" in Pickering
LunaRating, 5 stars1 week ago
Brendan was super accomodating, the space was comfortable, clean and spacious and there clearly has been a lot of attention to detail put into making it a comfortable stay. Would stay there again in a heartbeat!

Flat in Pickering Beach
4.77 out of 5 average rating, 201 reviewsLuxurious Private Suite by the Lake
DavidRating, 5 stars1 week ago
Audette was very responsive and even helped me with ordering in my budget and having flowers for my girlfriend prior to when we arrived! Love the cleanliness of how beautiful the place is and would rent again! Very well worth the price and the top notch service to provide guests like me a place to stay in a very nice and peaceful neighborhood!! Thank Audette for hosting us and we will be back!
Top guest favourite

Home in Pickering
5 out of 5 average rating, 9 reviewsModern Nest - Pickering 5 beds, 2.5 baths, 3 park
NashiaRating, 5 stars3 days ago
We were in town for a family wedding and stayed at this Airbnb. The hosts had a lovely home that was suited for our needs. Great communication, and the place is just as it is pictured! We had one issue that was addressed as soon as we messaged the host which is very greatly appreciated! Would definitely stay again!

Home in Pickering
4.75 out of 5 average rating, 4 reviews1 bedroom studio private basement in Pickering
MelanieRating, 5 stars1 week ago
Mohammed was a great host! The place was very clean, cozy and comfortable!
Top guest favourite

Home in Pickering
5 out of 5 average rating, 7 reviewsLuxurious Home Away From Home
GabriellaRating, 5 stars2 weeks ago
Really enjoyed my stay here. The place was just like the photos; clean, cozy, and comfortable. The living room had a nice, relaxing vibe and the kitchen had everything I needed to cook full meals. The host was polite and helpful, and check-in was super easy with a door code. Everything was clean, including fresh sheets and towels. I appreciated the little extras like bottled water, kitty snacks, and a great selection of teas and hot drinks. The Wi-Fi worked well the whole time. Great location too. Close to Walmart, Dollar Store, and a cute dessert café. Would definitely stay here again.
Top guest favourite

Flat in Pickering
5 out of 5 average rating, 7 reviewsKing & Queen Suite Pickering Casino
CheyenneRating, 5 stars1 week ago
BOOK THIS PLACE!!! You won’t regret it!!! Not only is Tracy absolutely delightful to do business with, she is such a welcoming and caring host! I highly recommend staying at The Love Nest by Tracy! ✨✨🩷🩷🩷 I felt so at peace In her beautiful home! It was so clean plus I had the best view of the city and beach/ lake! 😍 I absolutely loved it and will definitely be staying at any of Tracy’s suites again! The King Bed was sooooo comfortable, I felt like I was sleeping on a cloud! ☁️ 😌 … the balcony was such a treat as well! So well decorated, it provided the perfect ambiance to wind down and relax! Thank you so much Tracy! You are the best! I can’t wait to book with you again in the future! I will recommend your Airbnb to everyone I know! 🫶🏾✨🩷
Guest favourite

Home in Ajax
4.92 out of 5 average rating, 25 reviewsPrivate Sauna Suite Retreat
Cris AndreaRating, 5 stars2 days ago
We enjoyed our one-night stay at Najia's place. The space was spacious and well-maintained, making for a comfortable experience. The sauna was a nice addition as well. While having a kitchen could enhance the stay even further, overall, it was a positive experience. Highly recommended!
Quick stats about holiday rentals in Pickering
Total rentals
1.5K properties
Total number of reviews
36K reviews
Family-friendly rentals
610 properties are a good fit for families
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
50 properties have a pool
Rentals with dedicated workspaces
940 properties have a dedicated workspace
Destinations to explore
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- Guest house rentals Pickering
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- BMO Field
- Massey Hall
- Trinity Bellwoods Park
- Casa Loma
- Dufferin Grove Park
- Jackson-Triggs Niagara Estate
- Royal Woodbine Golf Club
- Royal Ontario Museum
- Nathan Phillips Square
- Christie Pits Park