Oshawa vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Oshawa

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

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Guest favorite

Apartment in Whitby

4.97 out of 5 average rating, 313 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😊

Aug 3 – 10

G$21,440 GYD per night

Guest favorite

Guest suite in Courtice

4.98 out of 5 average rating, 110 reviews

***Cozyer n Courtice*** (private apt/own entry)

self-contained, private apt/suite/own entry. [Rates are CDN not US] Spacious bedroom/fireplace/4 piece bathroom. Private living/dining area with cable TV and Wifi. Own entry. Kitchenette/Small Sink/Fridge&Microwave (provide own dishes/cutlery). Located just 6 minutes north of the 401. Close proximity to the 407, 115 and soon to be 418 hwy. Close to Darlington Power Plant and other local businesses. GO/local bus service, restaurants and shopping. Please ask, if earlier check-in required.

Jun 21 – 28

G$10,610 GYD per night

Guest favorite

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!

Dec 12 – 19

G$16,281 GYD per night

Guest favorite

Guest suite in Ajax

4.95 out of 5 average rating, 397 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.

Jun 13 – 20

G$19,487 GYD per night

Guest favorite

Apartment in Oshawa

4.95 out of 5 average rating, 616 reviews

Just like home

This is an fully furnished basement apartment Quiet neighborhood close to bus stop, shopping and restaurants. Ten minute drive to Oshawa Center and downtown Oshawa. Reserve parking in driveway on left side. Breakfast ingredients are included; Eggs, Bacon, Cereal ,Toast, Coffee , Tea and etc. Our guests can rest assured that the bedding is washed and changed with each and every new guest, and for those who stay for a week or more , bedding is changed every five days or upon request.

Sep 12 – 19

G$11,027 GYD per night

Guest favorite

Apartment in Pickering

4.93 out of 5 average rating, 107 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.

Mar 8 – 15

G$16,953 GYD per night

Guest favorite

Home in Whitby

4.78 out of 5 average rating, 201 reviews

Entire House, Central Whitby on a quiet street

NO CLEANING FEE, ENTIRE HOUSE 4U. Two nights minimum, thank you. Cute house w/new modern appliances, hardwood floor in Central Whitby. Backyard and patio for your relaxing moments. ABSOLUTELY NO PARTIES, no indoor SMOKING (of any kind). Only the no. of people who booked to be in the house. This is a quiet neighbourhood and should stay the same, there are party rooms avail on this site:) Again, many thanks. I don't charge any cleaning fee, but please be considerate.

Apr 22 – 29

G$21,759 GYD per night

Guest favorite

Apartment in Oshawa

4.92 out of 5 average rating, 142 reviews

Modern, Cozy Getaway with a Great View !

This is a beautiful modern and private space, backing onto a scenic ravine. This suite is perfect for singles , couples, small families, professionals, mini getaway or anyone visiting the area. It includes a spacious bedroom with fireplace, a fully stocked eating area, a modern living room with a fireplace, bathroom with double vanity, laundry washer/dryer, free Wi-Fi, BBQ and contactless check-in/check-out. STR Operator Licence #202210008

Sep 7 – 14

G$21,677 GYD per night

Guest favorite

Guest suite in Oshawa

4.9 out of 5 average rating, 157 reviews

Private guest suite close to downtown Oshawa

This 2-storey addition at the back of the house is perfect for solo travellers or a couple. It has a private entrance and is completely separate from the main house. The house is in a safe and quiet residential neighbourhood and it is a 15 minute walk to downtown Oshawa where there are restaurants, bars, and the Tribute Centre. It is also close to the GO bus (with access to the GO train into Toronto) and local buses.

Apr 28 – May 3

G$15,580 GYD per night

Guest favorite

Guest suite in Whitby

4.9 out of 5 average rating, 457 reviews

Canadiana Suite private entry, walk to Thermëa Spa

We welcome travellers "from away" to our Canadiana themed guest suite. Here you will see Canadian artwork and sculptures and hopefully learn something new about Canada! In addition, we have refinished much of the furniture in the space ourselves. Each piece has its own story. We are located 2 km away from the Thermëa Spa, which attracts many of our Airbnb guests.

Jun 16 – 23

G$14,467 GYD per night

Guest favorite

Home in Whitby

4.94 out of 5 average rating, 151 reviews

Beautiful stylish home

Perfect for SPA. SKI. OPG. Port Whitby, Marina. Sport Teams. ENTIRE HOME Renovated and newly furnished. All amenities: Internet, Wifi, Netflix, Disney+, Spotify, Bar, Bonzini Foosball Table, trail in your backyard, walking distance to GO, 3min to Hwy 401. Calm neighborhood with many facilities: restaurants, shopping centers, movie theatre, playdium and more.

Feb 13 – 20

G$25,901 GYD per night

Guest favorite

Apartment in Oshawa

4.89 out of 5 average rating, 220 reviews

Lovely 1-bedroom apartment rental in NE Oshawa

This stylish place to stay is perfect for a single individual or couple visiting Oshawa. (Adults only) A legal basement apartment with a queen bed, has a separate entrance, and includes all the amenities needed for a home away from home. Includes: Toaster, microwave, Keurig machine, dishes and cutlery, pots and pans, dishwasher, and laundry machines.

Sep 14 – 21

G$15,468 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oshawa vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oshawa's top sights

Oshawa Centre81 locals recommend

Tribute Communities Centre21 locals recommend

Metro10 locals recommend

Iroquois Park Sports Centre13 locals recommend

Durham College9 locals recommend

Sky Zone Trampoline Park55 locals recommend

Other great vacation rentals in Oshawa

Guest favorite

Home in Whitby

4.82 out of 5 average rating, 118 reviews

Cheerful 4-bedroom home with huge patio

Oct 2 – 9

G$30,194 GYD per night

Guest favorite