Holiday houses in Oshawa

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Top-rated holiday rentals in Oshawa

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

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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
4.96 out of 5 average rating, 220 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
A spacious living area showcases a comfortable gray sofa facing a television on a light-colored media console. A dining table with chairs is positioned nearby, alongside a fully equipped kitchen with white cabinetry and modern appliances. Natural light enters through a window, enhancing the bright ambiance.
Guest suite in Whitby
4.9 out of 5 average rating, 101 reviews

Full independent basement unit (separate entrance)

Enjoy this independent, bright, spacious & serene space in a family friendly and safe neighbourhood! Full basement with separate entrance, private full kitchen, private full bathroom, queen bed, TV (BellFibeTV, SportsNet,TSN,Netflix..), 1.5G Fibre Wifi, cookware, utensils. Walk to major Rds: Taunton & Thickson, amenities & bus stops. 10 min drive: GoTrain, 401, 407 All sheets & pillow cases are washed and sanitized before guests check-in. No pet, No smoker, No guest! Under video surveillance!

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, 244 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 in 2021, 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.

Superhost
A modern living area features a sleek black television mounted on a white stand. A round glass coffee table sits in front, topped with a small decorative plant. Light-colored walls and warm wood flooring create a bright and open atmosphere.
Home in Bowmanville
4.76 out of 5 average rating, 119 reviews

Home in bowmanville

Premium accommodation for travellers and bussiness people, Entire private one bedroom unit with full kitchen and bathroom, seperate side entrance with Clean and spacious rooms. 6 minutes to highway 401 . Many restaurants are near by. Free private parking . Ready to have your coffee and toast and enjoy your trip to Bowmanville. One hour to Toronto downtown.This place is a premium accommodation, not animal friendly so please don’t book with your pet. Strictly No doping allowed.

Guest favourite
The modern exterior of the house showcases a blend of stone and brick materials. Sunlight reflects off the upper windows, highlighting the clean lines and architectural features. A spacious driveway leads to the garage, complemented by neatly manicured grass.
Home in Bowmanville
4.92 out of 5 average rating, 232 reviews

Cozy Lakeside Modern House 4Br - Steps To The Lake

Great place to get away to the lakeside, family get together, relax, enjoy downtime. Tons of space for everyone in this 2,800 Square ft brand new modern home in the waterfront community in Bowmanville. Just a few steps to the walking trails, biking trails, beaches, playground & splash pad. Enjoy your stay with a walk when sunset or sunrise on the trails. Come and relax with a coffee by the fireplace on chilly days, or outside by the porch on warm summer days.

Guest favourite
A cozy living space is highlighted by a wooden dining table surrounded by upholstered chairs. A kitchen area features a bar counter and modern appliances, while a comfortable seating area boasts plush chairs and a stone fireplace. A large wall screen displays a vibrant gaming scene.
Guest suite in Whitby
4.95 out of 5 average rating, 126 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, 203 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, 396 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 living area features a spacious couch and two cozy blue accent chairs, positioned around a round coffee table. A large flat-screen TV is mounted on the wall, while a modern mirror reflects the open concept layout, enhancing the light from the recessed lighting.
Home in Ajax
5 out of 5 average rating, 121 reviews

Ultra-Modern Luxury Retreat! Close to Thermea SPA.

COZY and INVITING, this modern suite is in a quiet, family-friendly Ajax neighborhood. Just 10 minutes to Thermea Spa and Ajax GO Station, and a short walk to parks, shops, and groceries. Newly built with deluxe finishes, the 1,000 sq. ft. space includes in-floor heating, an electric fireplace, a spacious sofa, and smart TV with Netflix/Prime. Downtown Toronto is 35–45 mins by car, and Pearson Airport or Mississauga in about 55 mins.

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, 130 reviews

Spacious Guest Room 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
4.91 out of 5 average rating, 116 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
A modern living space is displayed, featuring a wall-mounted television above a sleek dark cabinet. To the right, a laundry area is visible with stacked washer and dryer units. Light hardwood flooring runs throughout the space, contributing to a clean and contemporary look.
Home in Pickering
4.93 out of 5 average rating, 129 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

Popular amenities for Oshawa holiday rentals

When is the best time to visit Oshawa?

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Avg. price$96 AUD$99 AUD$96 AUD$104 AUD$104 AUD$109 AUD$112 AUD$115 AUD$106 AUD$102 AUD$102 AUD$101 AUD
Avg. temp-3°C-3°C2°C8°C14°C20°C23°C22°C18°C11°C5°C0°C

Frequently Asked Questions

  • How is the weather in Oshawa?

    Oshawa experiences a temperate climate. Summer temperatures average around 77°F (25°C) while winter temperatures can drop to 16°F (-9°C). During winter, Oshawa is a destination for various snow-based activities.

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

    Popular activities include exploring the Oshawa Museum, visiting the Robert McLaughlin Gallery, and taking a leisurely walk in the Oshawa Valley Botanical Gardens. For sports enthusiasts, catching an Oshawa Generals hockey game is a local favorite.

  • What is the best time of year to visit Oshawa?

    Summer, from June to August, is the most popular time to visit Oshawa. During these months, you can explore events like the Peony Festival in June and Fiesta Week in June, celebrating the city's multicultural heritage.

  • What are the best places to stay in Oshawa?

    Popular areas to stay in Oshawa include the downtown area for its close proximity to attractions, Lakeview for its beautiful vistas, and Stevenson for its quiet suburban charm. Choose a location that aligns with your travel preferences.

  • What are the best places to visit in Oshawa?

    Visitors to Oshawa frequently appreciate the Canadian Automotive Museum, which chronicles the country's car history. The Oshawa Zoo and Fun Farm is often recommended for families, housing over 40 species of friendly and tame animals. The Parkwood National Historic Site and the Robert McLaughlin Gallery are also among the popular attractions for culture and art enthusiasts.

  • What are some hiking trails in Oshawa?

    Hikers can explore trails like the Harmony Creek Trail, the Waterfront Trail, and the Second Marsh Wildlife Area. These trails provide a mix of urban and natural scenery, with opportunities to spot local wildlife.

  • What are some family activities to do in Oshawa?

    Families can explore the interactive exhibits at the Ontario Regiment Museum, enjoy picnics at Lakeview Park, or have fun at the Neb's Fun World for arcade games and bowling. The Oshawa Zoo and Fun Farm is often recommended for its variety of animals.

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

    Great day trip ideas include visiting the Canadian Automotive Museum, exploring the Parkwood National Historic Site, or spending a day at Darlington Provincial Park. Nature enthusiasts may enjoy a visit to the Oshawa Valley Botanical Gardens.

  • Are there vacation rentals with a dedicated workspace in Oshawa?

    Yes! Work meets play with ease at over 370 vacation rentals in Oshawa featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Oshawa?

    Four-legged friends are welcome in Oshawa. Choose from more than 120 vacation rentals for guests traveling with pets.

  • Are there Oshawa vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Oshawa, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in bungalow rentals in Oshawa?

    Experience the best of Oshawa with our bungalow rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Oshawa have a gym?

    Absolutely! We offer over 20 apartment rentals with a gym in Oshawa. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oshawa have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Oshawa. Enjoy a tailored experience with all the comforts you desire.

  • Do guesthouse rentals in Oshawa have air conditioning?

    Absolutely! We offer over 10 guesthouse rentals with air conditioning in Oshawa. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Oshawa have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Oshawa. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Oshawa?

    Oshawa has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Bed And Breakfast Rentals in Oshawa?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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

Destinations to explore

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