Holiday houses in Oshawa

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Top-rated holiday rentals in Oshawa

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Guest favourite
A modern kitchen is presented, featuring sleek white cabinetry and a textured backsplash. Stainless steel appliances, including a refrigerator and oven, are prominently displayed. A countertop offers space for meal preparation, while a coffee maker and microwave add to the kitchen's functionality.
Guesthouse in Whitby
4.97 out of 5 average rating, 233 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
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, 102 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.

Guest favourite
A well-maintained exterior of a single-story brick residence is highlighted, featuring a manicured lawn and vibrant flowerpots along the entrance. A vehicle is parked in the driveway, and decorative accents add a welcoming touch to the home.
Apartment in Donevan
4.93 out of 5 average rating, 861 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 spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.
Farm stay in Uxbridge
4.98 out of 5 average rating, 266 reviews

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes a sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Guest favourite
A cozy living space features a modern television stand with a flat-screen TV, accentuated by a bold artwork. A gray couch with yellow cushions invites relaxation, complemented by a light rug atop wooden flooring. Large windows allow natural light to brighten the room.
Home in Ajax
4.86 out of 5 average rating, 221 reviews

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!

Top Guest favourite
A cozy bedroom features a spacious bed with elegant bedding, flanked by two nightstands. A dresser is positioned against the wall, and natural light filters through a window, illuminating the soft grey walls and light-colored flooring.
Home in Ajax
4.98 out of 5 average rating, 107 reviews

Private Sauna Suite Retreat

1 Bedroom • 1.5 Bathrooms • Private Entire Unit Newly renovated and quiet, just minutes from Hwy 401 and local restaurants. Highlights • Private self check-in • Driveway parking for 1 car • Private sauna • 55 Inch TV with Netflix Amenities Fresh towels, linens, tooth brushes & pastes, hairdryer, home essentials, shower essentials, and extra pillows/towels on request. Spotless home, quick replies, and your comfort guaranteed - book with confidence.

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
4.84 out of 5 average rating, 212 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.

Top Guest favourite
Apartment in Whitby
4.96 out of 5 average rating, 400 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🍷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😊

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, 133 reviews

Spacious Guest suite close to 401

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

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
4.92 out of 5 average rating, 128 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, 160 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.

Guest favourite
A modern living area features a pair of vibrant blue sofas arranged around a decorative area rug. Large windows allow natural light to brighten the space, complemented by a sleek kitchen with dark cabinetry and stainless steel appliances visible in the background.
Home in Whitby
4.86 out of 5 average rating, 211 reviews

Luxurious & Modern Guest Suite-Walkout Bsmt Apt.

Luxurious new constriction basement apartment in central Whitby. Gorgeous kitchen, living area, and laundry. Ravine lot with excellent views of forest nearby. One stunning bedroom and one 3pc bath. One Free parking on the premises! Please keep in mind we do have a dog on the property. Please note: The kitchen only has a wine fridge. We do not have a freezer.

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 690 holiday rentals in Oshawa

  • Nightly prices starting at

    Oshawa holiday rentals start at $15 AUD per night before taxes and fees

  • Verified guest reviews

    Over 15,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    370 properties have a dedicated workspace

  • Wi-Fi availability

    670 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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