Holiday houses in Pickering

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Top-rated holiday rentals in Pickering

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Guest favourite

Guest suite in Pickering

4.89 out of 5 average rating, 106 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!!

31 May – 7 Jun

$190 NZD per night

Guest favourite

Guest suite in Pickering

4.94 out of 5 average rating, 124 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.

22–29 Jun

$206 NZD per night

Guest favourite

Guesthouse in Pickering

4.96 out of 5 average rating, 27 reviews

Luxury Ground-Level "Suite Escape"

"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

4–11 Feb

$214 NZD per night

Guest favourite

Apartment in Whitby

4.95 out of 5 average rating, 152 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!

28 May – 4 Jun

$147 NZD per night

Guest favourite

Guest suite in Ajax

4.95 out of 5 average rating, 395 reviews

Walk Out Basement Apartment W/Separate Entrance

PRIVATE Walk Out Basement Apartment W/Separate Entrance. 420 Sq.Ft space. Queen Sized Bed. Oversized Shower w/ Rainfall Shower-head. Small Kitchenette w/ Microwave, TWO Mini Fridges, Coffee/Hot Water Tea Maker. Dining/Work Table w/Benches. High Speed Wi-fi. Living Room w/ Reclining Lazy Boy Couch and 50” Smart Tv. Over 1000 Live Tv Channels and Netflix. Private Little Backyard Patio w/Table. Private Driveway (Parking For 2 Cars). 1 Min Drive to Hwy 401. 15 Min Walk to Ajax Go Station.

13–20 Jun

$176 NZD per night

Guest favourite

Apartment in Pickering

4.94 out of 5 average rating, 106 reviews

Walk-out Basement Guest suite w/Fibe & Parking

My family of 4 lives upstairs and are available for any support, questions or concerns. We like to give our guests their privacy during their stay but I am available when needed. The unit comes with Bell Fibe wifi, free parking, and a tv with 1000+steaming channels, Netflix, Prime, AppleTV. Need a place to watch the game or fight?We got it! Our Airbnb is within driving distance to several popular restaurants, bars, shopping and casinos. An ideal central base to explore Pickering.

24–31 Dec

$137 NZD per night

Guest favourite

Home in Pickering

4.84 out of 5 average rating, 150 reviews

Tranquility by the Marina | 3 Bedroom Open Concept

Relax with the whole family in the upstairs unit of this legal duplex. Equipped with a private entrance, your unit will have no shared spaces. Your stay is walking distance to the Marina, Pickering GO station and several restaurants. This 3 Bedroom residence is located within minutes to the 401 and exactly 10 minutes to the newly opened Pickering Casino. Open concept kitchen and living space is highlighted by a 65" LG OLED smart TV. This 3 PC Bathroom comes with a soaker tub.

19–26 May

$267 NZD per night

Guest favourite

Apartment in Pickering

4.91 out of 5 average rating, 107 reviews

Lower Unit - Central location

Enjoy the charming touches of this cozy basement suite with a clean modern feel. Beautifully decorated featuring a spacious open concept living room/kitchen combo area with spacious island and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is bright and full of warmth. Conveniently located: 5 min walk to Pickering Town Center, 10 min walk to the Pickering GO and 2 min drive to 401.

26 Feb – 5 Mar

$173 NZD per night

Guest favourite

Guesthouse in Pickering

4.94 out of 5 average rating, 16 reviews

Spacious fully private studio basement & parking

This large bachelor unit in basement is newly renovated. Fully private and separate entrance. This place is great for a romantic getaway and it's 5 min driving to Frenchman's Bay Beach. Wifi and TV with free Netflix and Crave installed. The kitchen is spacious with full appliances, Fridge, Stove, Microwave, Coffee maker, Toaster and Kettle. Dishes and cookware are available in the kitchen. Laundry is private.

27 Apr – 4 May

$134 NZD per night

Guest favourite

Guest suite in Pickering

4.92 out of 5 average rating, 186 reviews

Private Suite steps from Frenchman's Bay

Welcome to your home away from home! Spend your stay in Pickering in a clean private suite with a separate side entrance. There is free parking in a friendly and quiet neighborhood. Conveniently located 5 minutes from the 401, and the Pickering Go station, making it easy to travel to downtown Toronto. Lots of nature and 5 minute walk from the beach. Only 15 minute drive from the new Pickering Casino Resort!

1–8 Jul

$161 NZD per night

Guest favourite

Apartment in Pickering

4.87 out of 5 average rating, 203 reviews

Charming, Spacious Bsmt Apartment in Pickering

This is a spacious newly renovated basement with separate entrance located on Appleview Road, Pickering. It has three bedrooms and two bathrooms. While it is in a quiet and pleasant neighbourhood, it is also close to the Pickering Town Centre, High Way 401, and Go Train Station. This apartment is very suitable for family as it is a comfy, clean, and warm environment.

19–26 Sep

$201 NZD per night

Guest favourite

Guest suite in Pickering

4.87 out of 5 average rating, 547 reviews

* HOT TUB* Guest Suite Steps to the Beach!

Welcome to the Romanic Zen Den! Your separate entrance will lead you to your lower level of the bungalow and is the perfect place to find your inner zen after enjoying the beautiful outdoors of Pickering. Elevate your experience with add-on packages! *we live on higher level *9 pm please no loud noise outside

28 Jun – 5 Jul

$236 NZD per night