Holiday houses in Pickering

4.94 out of 5 average rating, 284 reviews

Condo in Pickering

“Elysium” Where happiness is real!

Stay connected with our fast Bell Fibe Wi-Fi, free parking and unwind with over 1000 streaming channels on our TV, including Netflix and Prime. Whether you're here to catch the game or watch an exciting fight you’ll have everything you need for a great time Our location is the perfect base for discovering all that Pickering has to offer. You’ll be just a short drive away from fantastic restaurants, lively bars, shopping spots, and even casinos—everything you need for a fun and convenient stay!

5 out of 5 average rating, 109 reviews

Home in Ajax

Ultra-Modern Luxury Retreat! Close to Thermea SPA.

Cozy and welcoming, located in a quiet and family-friendly neighborhood; it is a terrific offering that will impress guests. It is centrally located in Ajax and 10 min from Thermea Spa, newly built with deluxe finishes situated within walking distance to superb services, including groceries, parks, and shops. The space is approximately 1,000 sq. ft in total, with in-floor heating. The modern electric fireplace sits in front of the expansive couch, with a TV with Netflix and Prime Video access.

4.88 out of 5 average rating, 688 reviews

* HOT TUB* Guest Suite - Minutes to the Beach!

Welcome to the Hidden Gem - 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! *there is another guest unit on the main floor. You will hear signs of life from above *9 pm pls no loud noise outside 4 min walk to Beach 12 min Casino 11 min Zoo 7 min Mall/Movies 18 min Thermea Spa 30 min Dwntwn Toronto

5 out of 5 average rating, 4 reviews

Home in Ajax

Newly Modern Lakeside House

Newly Renovated & Comfortable Space: Featuring a modern design, bright and spacious layout, and brand-new furniture, ensuring a premium living experience. Convenient Transportation: Centrally located with easy access to highways and public transit, making travel a breeze. Fully Equipped Amenities: Close to Costco, No Frills, Walmart, and other supermarkets . Our property is near the scenic Pickering waterfront and beach, perfect for morning jogs, peaceful strolls, or watching stunning sunsets.

4.97 out of 5 average rating, 79 reviews

Guesthouse in Pickering

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.

4.9 out of 5 average rating, 41 reviews

Apartment in Pickering

Beautifully renovated apartment

Located on a quiet cul-de-sac right beside the popular Seaton Trail. Self-check into your beautiful walk-out apartment. Relax and watch the birds in the back yard. Parking included. Large windows provide natural light. There are 2TV's !Netflix and Amazon Prime). The bedroom has a queen bed. Elegant bathroom with oversized shower. Easy access to downtown Toronto, by transit or highway. A short drive to numerous shops and excellent restaurants, a huge new casino, and Toronto Zoo.

4.91 out of 5 average rating, 225 reviews

Urban HotTub Oasis/Porsche Experience Center 10min

Completely private studio suite with cozy queen bed and kitchenette (no full kitchen) Exclusive hot tub access for ultimate relaxation Modern space with Fireplace and smart TV for streaming Fast Wi-Fi and dedicated parking included Approximately 30 minutes from downtown Toronto Conveniently located near Thermea Spa and Frenchman’s Bay, Pickering Casino Resort & Toronto Zoo One parking spot for SUV size car. Safe and secure with a disclosed entrance camera and responsive hosting

4.84 out of 5 average rating, 176 reviews

Home in Ajax

Moons & Noons -Separate Unit for your Comfort

Welcome to our charming retreat in Ajax! You'll be greeted by living space adorned with carefully curated decor. The sofa beckons you to unwind, while the large windows' scenic views allow natural light to fill the room. Just take a stair down to the Basement, to be greeted by an elegant kitchenette. Enjoy a drink on the sofa while watching shows on 55' QLED. Step into a world of relaxation in our stunning bathroom designed to calm your stress. Your unforgettable stay awaits U!

4.98 out of 5 average rating, 114 reviews

Chefs Kitchen I TorontoZoo I 8km to EV Chrg I Park

Why you will love your stay here: - ***ENTIRE HOME*** No one will be on the property but those on the booking. This is a DETACHED house. No connecting houses. - Open concept on the main floor so you can connect and create memories - Dedicated work from home spaces . Cat 6 ports -The 2nd floor has 4 different rooms where you can unwind and take a much deserved break - 10ft ceilings on a corner lot with lots of sunlight - Central Hub to Toronto (45 min drive)

4.79 out of 5 average rating, 191 reviews

Muskoka on the City

Property situated on Rouge National Urban Park, close to Toronto zoon, seaton trail. step to beautiful lake and beach , you will enjoy hiking,kayak ,bike and fishing.Close to highway,resultant,shopping mall,public transport, Rouge Hill GO Station. bright in ground suite .kitchen ,dinning room in basement with TV, private bathroom(basement), and private entrance(back yard). Suite has a separate bedroom with a queen sized bed, free wireless internet, and full laundry.

4.92 out of 5 average rating, 179 reviews

Apartment in Pickering

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.

4.97 out of 5 average rating, 63 reviews

Luxurious, modern basement unit

Kick back and relax in this calm, stylish space. Prime location near bus stop, shops, restaurants there is something for everyone. Whether you are here for work or pleasure this is your best place. Your home away home. Nice and modern new basement apartment with fast and reliable fibe internet , smart TV with Netflix, Amazon prime and Disney plus , dedicated work space and free parking

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Popular amenities for Pickering holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pickering

5 out of 5 average rating, 10 reviews

"Suite Escape" in Pickering

LunaRating, 5 stars2 days 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!

4.97 out of 5 average rating, 64 reviews

Relaxing Private 1-bdrm apt Surrounded by Nature

GunjeetRating, 5 stars2 weeks ago

The place matched the listing, well-equipped and spacious, it finds itself in a quiet area with nearby trails to explore. Self check-in with very clear and helpful instructions. Finally, the host is very responsive and kind, always available whenever needed. I recommend it 200%. don't shy away to meet Friday as well.

Apartment in Pickering Beach

4.77 out of 5 average rating, 199 reviews

Luxurious Private Suite by the Lake

TamiliaRating, 5 stars2 weeks ago

I had an amazing stay. This is definitely the BEST Airbnb I’ve ever stayed at. Everything was organized and I felt right at home. Personal hygiene essentials were made available as well along with some snacks in the kitchen. I look forward to coming back for another stay.

4.77 out of 5 average rating, 88 reviews

Beach House: First Floor

IssyRating, 5 stars2 weeks ago

This place was amazing specially with the pool table it’s a nice touch. You won’t get bored. Lots to do around there and only a few minutes walk to the beach. We enjoyed our stay. The location was great. Will definitely do it again. Thank you Tanzila.

5 out of 5 average rating, 7 reviews

Modern Nest - Pickering 5 beds, 2.5 baths, 3 park

KaltunRating, 5 stars2 days ago

Ari is a great host and communicates very well with her guests. The house was beautiful and neat, looks exactly how it does in pictures. Ari is always available to help with any concerns and is a generous host. Will book again if I’m staying in the area.

4.91 out of 5 average rating, 151 reviews

Wake up in MapleTree Oasis•2 bedroom in Pickering

KariRating, 5 starstoday

Li is very sweet! I loved having breakfast on the outside patio. It’s a little quiet oasis! Great value and lots of room. If the living room couch pulled out this would easily sleep 6. Great times had!

4.83 out of 5 average rating, 93 reviews

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

RobinRating, 5 stars2 weeks ago

Daniella and Stephen's place was perfect for the 3 of us. They were quick to respond to questions we had. Their home was like being inour home away from home and more!!! We definitely will be back next year. Thank you Daniella and Stephen for making our stay so comfortable.