Vacation rentals in Pickering

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Top-rated accommodation in Pickering

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Apartment in Whitby

4.97 out of 5 average rating, 310 reviews

LOVE and Relax at Dream Catcher Retreat

Are you looking for the perfect getaway? 😊 Retreat yourself to a Luxurious, Charming and Modern Suite with a splash of glam.✨ Perfect for couples, families or business trips. Enjoy the Fireplace with a glass of Cabernet Sauvignon🍷, Whilst enjoying a good movie on HDTV using Chromecast. Perhaps you would also like to partake in a game of pool on our custom pool table 🎱, or take a hot rainfall shower in a delightful Stone Spa Shower💦. But, most importantly, our place is yours to relax and unwind😊

15–22 Jul

$183 NZD per night
Guest favourite

Guest suite in Pickering

4.88 out of 5 average rating, 103 reviews

*Hotub* Walkout Patio* Separate Unit* Inlaw Suite!

Oasis of country & city life in North Pickering!! We offer an above ground (main floor) fully private in law suite in greater Toronto with a separate entrance! 8 min drive to train station to Toronto & half hour drive to downtown Toronto. Amenities include: free parking for a SUV size car, wifi, 4K tv/cable, air conditioning, fridge, keurig, kettle, microwave/air fryer, laundry, garden patio! and ***Jacuzzi ***Hotub with jets and LED lights 10-15 min drive to local attractions in listing pics!!

25 Apr – 2 May

$161 NZD per night
Guest favourite

Guest suite in Pickering

4.93 out of 5 average rating, 123 reviews

Separate 2 Bedroom & 2 Washroom up to 4 people.

Hotel-style apartment in a home annex. Not a basement. The apartment has 2 bedrooms with attached washrooms, Living area, kitchen, dining. Our property accommodates up to 4 people. Children are welcome to stay. Conveniently located just off Highway 401. Close to downtown Pickering, Go Station, mall, restaurants. We are a good stopover point if you are traveling to downtown Toronto which is only a 40 min drive. Note: Show us your ID when "Checking In" and it has to match with your booking name.

24 Apr – 1 May

$207 NZD per night

Popular amenities for Pickering accommodation

Stay near Pickering's top sights

Pickering Town Centre45 locals recommend
Toronto Pan Am Sports Centre26 locals recommend
Ajax Waterfront Park17 locals recommend
Costco Wholesale7 locals recommend
Beachfront Park8 locals recommend
Port Union Waterfront Park10 locals recommend

Other great accommodation in Pickering

Guest favourite

Guest suite in Pickering

4.9 out of 5 average rating, 30 reviews

Love to Travel

21–28 Jan

$119 NZD per night
Guest favourite

Home in Pickering

4.8 out of 5 average rating, 54 reviews

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

23–30 Oct

$255 NZD per night
Guest favourite

Condo in Pickering

4.89 out of 5 average rating, 18 reviews

Quiet oasis minutes from Toronto

16–23 Sep

$154 NZD per night
Guest favourite

Apartment in Pickering

4.94 out of 5 average rating, 100 reviews

Walk-out Basement Guest suite w/Fibe & Parking

16–23 Feb

$137 NZD per night
Guest favourite

Bungalow in Pickering

5.0 out of 5 average rating, 22 reviews

Beachy bungalow

17–24 Apr

$244 NZD per night
Guest favourite

Guest suite in Pickering

4.88 out of 5 average rating, 42 reviews

Private Ground Level Studio | Separate Entrance

22–29 Jun

$130 NZD per night
Guest favourite

Apartment in Pickering

4.91 out of 5 average rating, 33 reviews

Rouge Valley National Park

25 Aug – 1 Sep

$153 NZD per night
Guest favourite

Guest suite in Pickering

4.96 out of 5 average rating, 70 reviews

Private | WiFi | Q Bed | TV | Desk | Cafe | Park

20–27 May

$125 NZD per night
Guest favourite

Guesthouse in Pickering

4.96 out of 5 average rating, 23 reviews

Luxury Ground-Level "Suite Escape"

15–22 Feb

$214 NZD per night
Superhost

Guest suite in Pickering

5.0 out of 5 average rating, 3 reviews

Zen Grove: Multi-Purpose Studio BSMT 1B/1B+Kitchen

29 Jun – 6 Jul

$173 NZD per night
Guest favourite

Apartment in Ajax

4.83 out of 5 average rating, 81 reviews

Luxurious Private Suite by the Lake

21–28 Dec

$130 NZD per night
Guest favourite

Guesthouse in Pickering

4.93 out of 5 average rating, 15 reviews

Spacious fully private studio basement & parking

20–27 Dec

$128 NZD per night

Quick stats about holiday rentals in Pickering

Total rentals

1.4K properties

Rentals with dedicated workspaces

840 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

220 properties allow pets

Family-friendly rentals

540 properties are a good fit for families

Total number of reviews

26K reviews

Destinations to explore