Holiday houses in Oshawa

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Top-rated holiday rentals in Oshawa

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Guest favourite
Guesthouse in Whitby
4.97 out of 5 average rating, 238 reviews

One bedroom apartment/guesthouse.

Welcome to your peaceful private getaway located north of the 401 in Whitby. Guest will have the entire apartment with separate entrance to themselves. This newly constructed apartment is equipped with a fully functional kitchen, bathroom, living room and bedroom. Apartment comes with Wifi, 43” television with Amazon Prime TV services. Guest will have a designated parking space on the driveway. Please refrain from smoking inside the unit, smoke alarm are interconnected, and are highly sensitive.

Top Guest favourite
Guest suite in Whitby
4.97 out of 5 average rating, 34 reviews

Studio by the woods

Enjoy a modern and private studio that features a private entrance & self check-in, full kitchen, full bathroom, and a cozy full bed—designed for a comfortable stay. Located 5min drive from Thermea Spa, restaurants, cafés, hiking trails and GO Transit for easy access to Whitby and TOR. Features: ✔️Premium essentials ✔️Full kitchen & Bathroom ✔️Filtered drinking water ✔️Soft, chlorine free water ✔️Separate entrance & Self check-in ✔️Complimentary Parking (1 spot) ✔️Coffee & Tea ✔️Coin laundry

Top Guest favourite
A two-story house with light yellow siding and a brown roof features a welcoming front porch, adorned with potted plants and furniture. Well-kept landscaping surrounds the house, offering a bright and inviting outdoor space under a clear blue sky.
Apartment in Whitby
4.95 out of 5 average rating, 257 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!

Top Guest favourite
The spacious studio features a queen-sized bed with a checkered comforter and decorative pillows. A large Samsung 55-inch Smart TV is positioned on the entertainment unit, offering various streaming options. A workstation is visible in the background, providing a comfortable space for productivity.
Guest suite in Bowmanville
4.97 out of 5 average rating, 110 reviews

The Cozy Cove Studio

Cozy and private 1-bed studio, ideal for short or extended stays, well-equipped for convenience and relaxation. ✔︎ Spacious private suite with full Bath ✔︎ 55-inch 4K TV with Netflix, Prime, Crave, Fibe TV, YouTube, etc ✔︎ Super Fast WiFi ✔︎ Self check-in ✔︎ Workstation ✔︎ 5 mins drive - 401, Downtown, Malls, Grocery, Pharmacy, Restaurants, Cineplex. ✔︎ Free Parking on driveway ✔︎ In Unit Washer & Dryer ✔︎ Kitchenette - Fridge, Microwave, Kettle, Toaster, Coffee maker, utensils & supplies.

Top Guest favourite
Apartment in Donevan
4.93 out of 5 average rating, 885 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, Waffles, 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.

Top Guest favourite
A cozy entertainment area is illuminated by soft ceiling lights. A large projection screen displays colorful visuals in front of a stone fireplace. Comfortable seating includes a gray armchair and a dark sectional sofa, complemented by a light rug underfoot.
Guest suite in Whitby
4.96 out of 5 average rating, 138 reviews

Maple Edge

In Whitby's sought-after Sommerset neighborhood, this Airbnb promises a perfect getaway. The well-appointed space includes a queen-sized bed for restful nights, a fully-equipped kitchen for delightful meals, and a spa-inspired bathroom with a deep-soaking tub and luxurious rainfall shower. Just minutes from Thermea Spa, guests can seamlessly transition from the Airbnb's comforts to the therapeutic wonders of Therma, creating an ideal haven for relaxation.

Guest favourite
A cozy living area is furnished with a light-colored sofa and two blue armchairs, creating a comfortable seating arrangement. A glass coffee table sits at the center, and a television is mounted on the wall displaying content. A piece of abstract wall art adorns the space.
Guest suite in Whitby
4.83 out of 5 average rating, 218 reviews

Two Bedroom Basement Apartment

Have fun with the whole family at this stylish place. This space has all the amenities including Free WIFI, Netflix, Laundry, and a full Kitchen. Only 6 minutes drive from highway 401, 10 mins drive from Oshawa Mall, 5 mins drive from down town Whitby, and 5 mins drive from Whitby Entertainment Centrum (Landmark Cinemas and Restaurants, Good Life Gym). Also close by are other kids entertainment places such as, Flying Squirrel, Sky Zone, and Reptilia.

Guest favourite
Home in Oshawa
4.95 out of 5 average rating, 20 reviews

Basement apartment in Oshawa

This stylish place to stay is perfect for individuals, professional workers, students or couples trips. Located in a safe, quiet neighborhood in Oshawa. Walking distance to the bus stops Close to Ontario Tech University, grocery stores & more Features: • Private entrance through the backyard• Fully furnished (includes dining table, sofa set, queen bed, 55" TV, fridge, microwave, toaster, etc.) • Private laundry No pets | No smoking

Top Guest favourite
A modern living area features a large flat-screen television mounted on a textured wall, surrounded by decorative accents. Comfortable seating with plush cushions is arranged to invite relaxation. Soft ambient lighting enhances the contemporary design, while a decorative coffee table adds functionality to the space.
Home in Oshawa
4.99 out of 5 average rating, 70 reviews

Ultra Luxury Suite in Oshawa

Welcome to your ultra-luxury 1-bedroom basement suite in the heart of Oshawa! Enjoy a stylish open-concept living space with modern finishes, a fully equipped kitchen, spa-inspired bathroom, and cozy bedroom retreat. Perfect for couples, solo travelers, or business guests. Located in a quiet neighborhood with easy access to transit, shopping, and dining. Your private getaway awaits comfort, class, and convenience all in one.

Top Guest favourite
The exterior of a modern home features a stone facade, highlighted by outdoor lighting. A decorative entrance is flanked by large planters filled with vibrant flowers. The driveway leads up to a garage with contrasting colors, enhancing the inviting atmosphere of the residence.
Guest suite in Oshawa
4.92 out of 5 average rating, 137 reviews

Spacious Guest Suite near 401 with parking

Welcome to our spacious and stylish 1 bedroom in the basement, perfectly suited for couples or individuals seeking a memorable stay. Nestled in a centrally located location, this hidden gem offers quick and easy access to all the amenities you could wish for. Centrally located, just 2 mins from the 401, gas stations, and McDonald's, and 5 mins from Costco. Durham College is a quick 15-min drive. License Number RHSTR2025001

Top Guest favourite
A small dining area is created with a round table covered by a patterned tablecloth. Two black chairs flank the table, which features a subtle floral centerpiece. A scenic landscape photograph hangs on the wall, adding visual interest to the space.
Home in Oshawa
4.93 out of 5 average rating, 144 reviews

Cozy Basement Suite in Oshawa

Welcome to Your Home Away From Home! Nestled in a peaceful neighborhood, our charming basement suite offers the perfect blend of comfort and convenience for travelers, whether you're here for business or leisure. Walking distance from shopping centers, restaurants, park and cinema hall. Very close proximity to Highway 401 and 407. This property is located in family friendly North Oshawa neighborhood.

Top Guest favourite
Apartment in Windfields
4.96 out of 5 average rating, 164 reviews

Family Friendly | HOT TUB | Near Toronto & UOIT

Newly built 1-bedroom private basement apartment in Oshawa featuring a work/study area, full kitchen, and in-suite laundry. Relax in the hot tub after exploring local trails, parks, and farms. Close to Ontario Tech University, Durham College, shops, and restaurants. Easy access to Durham Transit, GO Bus/Train, and Highway 407. Ideal for couples, professionals, or small families.

Popular amenities for Oshawa holiday rentals

When is the best time to visit Oshawa?

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Frequently Asked Questions

  • What are the best places to stay in Oshawa?

    Popular accommodations are often found in downtown neighborhoods, with easy access to dining, entertainment, and public parks. Those seeking quieter stays might consider residential areas near green spaces or the waterfront.

  • What are the best things to do in Oshawa with kids?

    Families often enjoy interactive museums, green spaces for play, and indoor entertainment centers. Seasonal activities such as local festivals or sporting events can be engaging for children, especially during summer and spring.

  • What are some of the best things to do in Oshawa?

    Oshawa has art galleries, museums exploring its automotive history, and public parks for walking or relaxation. Visitors also explore local markets and enjoy performances at community theatres.

  • How is the weather in Oshawa?

    Oshawa experiences cold winters around 20–33°F (-7–1°C), often with snow and rain, while summers are mild to warm, reaching 65–81°F (18–27°C). Spring and fall bring moderate temperatures with occasional rainfall.

  • When is the best time to visit Oshawa?

    Milder temperatures in late spring and summer are often recommended, with afternoons reaching 65–81°F (18–27°C). Seasonal festivals and blooming gardens can make these months especially appealing for visitors.

  • What are the best places to visit in Oshawa?

    The area has museums showcasing local heritage, botanical gardens, and vibrant lakeside parks. Art enthusiasts can explore gallery spaces, while history buffs often seek out historic homes and architecture.

  • What are some hiking trails in Oshawa?

    Oshawa has forested trails in urban parks, riverside paths, and nature reserves around the city. These trails are frequented for birdwatching, walking, and enjoying quiet woodland scenery.

  • What are some family activities we can do in Oshawa?

    Families can explore interactive museums, picnic in lakeside parks, or attend community art workshops. Seasonal festivals and public events often host kid-focused entertainment and performances.

  • What are some of the best day trip ideas from Oshawa?

    Explore waterfront communities around Lake Ontario, visit nearby parks known for scenic trails, or discover cultural attractions in neighboring cities. Many visitors also enjoy sampling regional foods on day trips throughout the area.

  • Are there any pet friendly accommodations available in Oshawa?

    Oshawa has pet-friendly vacation rentals in many neighborhoods, with some welcoming dogs or cats. Nearby parks and trails make it easy to spend time outdoors with your pet.

  • What are some local tips for visiting Oshawa?

    Consider exploring neighborhoods with vibrant murals and markets, and check out community events for unique local experiences. Early reservations are popular during major festivals and busy seasons.

  • What is Oshawa known for?

    Oshawa is frequently recognized for its automotive heritage, lively arts community, and proximity to Lake Ontario. The city also has a reputation for diverse food options and engaging cultural events.

  • What are the best hidden gems to explore in Oshawa?

    Seek out smaller art spaces, independent cafés with distinct décor, and community gardens tucked into residential areas. Some visitors enjoy strolling overlooked green spaces and discovering local mural installations.

  • What are the best foods to try in Oshawa?

    Oshawa’s dining scene includes locally inspired comfort dishes, international flavors, and bakery items. Popular choices often feature regional produce, classic Canadian fare, and creative cuisine from diverse cultures.

  • What should I bring for a trip to Oshawa?

    Pack layers for changing weather, comfortable walking shoes, and a rain jacket, especially in spring or fall. Sunscreen and hats are helpful for summer park visits, while winter requires insulated clothing and warm accessories.

  • What is the nightlife in Oshawa like?

    Oshawa’s nightlife has casual bars, pubs with live music, and cozy venues around downtown. Locals and visitors enjoy open mic nights, dance floors, and community events that highlight local talent.

  • What are the most popular events or festivals in Oshawa?

    Oshawa hosts music and cultural festivals in summer, seasonal community celebrations, and auto shows reflecting the city’s historical ties to car manufacturing. Fall events often highlight local arts and harvest traditions.

  • Are there family friendly vacation rentals in Oshawa?

    Oshawa has a selection of family-friendly vacation rentals in residential neighborhoods, often with amenities like kitchens, multiple bedrooms, and easy access to parks. Many families appreciate properties near entertainment districts or community centers.

Quick stats about holiday rentals in Oshawa

  • Total holiday rentals

    Explore 730 holiday rentals in Oshawa

  • Nightly prices starting at

    Oshawa holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 17,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    280 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 140 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    410 properties have a dedicated workspace

  • Wi-Fi availability

    710 of Oshawa holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oshawa rentals

  • 4.7 Average rating

    Oshawa stays receive an average rating of 4.7 out of 5 from guests

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