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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, 219 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 cozy lounge area features a large TV positioned on a wooden console. Comfortable armchairs and a loveseat in muted tones are arranged around a low coffee table. A floor lamp provides soft lighting, and a large window allows natural light to enhance the space.
Guest suite in Windfields
5 out of 5 average rating, 11 reviews

Luxurious 1 Bed, Ravine Facing Walkout Guest Suite

Kick back and relax in this 1 bed, 1 full bathroom, full kitchen with stainless steel appliances, fridge, dishwasher, washer dryer, stove, microwave and lounge with 65 inch TV calm, stylish space , backing into ravine, very quiet, cosy, and spacious. Ontario Tech university, Durham college, banks, Costco and other shops all at a distance of 3 to 5 mins. Hwy 407 , hwy 7 only 4 mins from home. Best for working professionals Needless to say you will unwind , relax and recharge yourself in no time.

Guest favourite
A cozy sleeping area features a queen bed dressed with a patterned blanket and vibrant throw. A nightstand with a small plant sits beside the bed. Soft, neutral tones create a calming atmosphere in this modern basement studio.
Home in Oshawa
4.8 out of 5 average rating, 60 reviews

Cozy Studio Retreat Oshawa | Private Entry

Welcome to your modern Oshawa retreat! Kick back and relax in this calm, stylish Oshawa basement apartment.Newly built and modern,it offers fast Fibe internet,a Smart TV with Netflix,and 2 free parking spaces.Guests enjoy complimentary coffee, tea, and a light breakfast.Conveniently located near bus stops, shops, and restaurants, with quick access to Highway 401.Close to Ontario Tech University and Durham College,this private retreat is perfect for work or leisure—your ideal home away from home.

Guest favourite
A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.
Guest suite in Pickering
4.87 out of 5 average rating, 733 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

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
4.99 out of 5 average rating, 91 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, 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 ✔︎ Washer & Dryer ✔︎ Kitchenette - Fridge, Microwave, Kettle, Toaster, Coffee maker, utensils & supplies.

Top Guest favourite
A modern living area features a sleek black sofa paired with a unique wooden side table. The table displays decorative books and a dried floral arrangement. In the background, a kitchen area is visible, showcasing contemporary cabinets and appliances.
Guest suite in Oshawa
4.97 out of 5 average rating, 37 reviews

New Elegant Suite, Free Parking

Discover comfort and style in our modern lower level suite, perfectly located in the heart of Oshawa. Just 13 minutes from the Oshawa Go station, this brand new, fully furnished home offers easy access to local colleges and downtown. Ideal for students, couples, or small families, enjoy a safe, luxurious stay with the convenience of free parking. The separate entrance ensures privacy in this cozy retreat. Book now for a blend of modern luxury and prime location!

Top Guest favourite
An open-concept living area features a large wall-mounted television against a marble design backdrop. A round coffee table is placed on a patterned area rug, with modern furnishings surrounding it. Soft lighting is provided by ceiling spots and highlighted elements on display.
Home in Oshawa
4.98 out of 5 average rating, 46 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, 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 modern entertainment table displays a PS4 console, two gaming controllers in black and white, and a collection of board games on shelves above. A colorful toy car adds a playful touch, while a large TV mounted above offers a clear view for gaming or movie nights.
Home in McLaughlin
4.92 out of 5 average rating, 13 reviews

BBQ + PS4: Sleek 3BR 1BA Home!

Welcome to our stylish Oshawa bungalow, freshly renovated for a fun, relaxing stay! Featuring 3 cozy queen bedrooms, a modern bathroom, spacious living room, and fully equipped kitchen. Minutes from shopping centers and HWY 401, it's perfect for convenience. IMPORTANT: Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

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, 114 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
The modern kitchen and living area feature sleek white cabinetry and stainless steel appliances. A light-toned island with seating is positioned near a comfortable sofa, which is complemented by decorative pillows. Soft lighting enhances the inviting atmosphere of this open-concept space.
Apartment in Windfields
4.96 out of 5 average rating, 154 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, 206 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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Avg. price$111 NZD$115 NZD$111 NZD$120 NZD$120 NZD$125 NZD$129 NZD$132 NZD$122 NZD$118 NZD$118 NZD$116 NZD
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 360 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 100 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 bed and breakfast rentals in Oshawa?

    Experience the best of Oshawa with our bed and breakfast rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Oshawa have a gym?

    Absolutely! We offer over 30 house 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 condo rentals in Oshawa have air conditioning?

    Absolutely! We offer over 10 condo 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 house rentals in Oshawa?

    Oshawa has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Townhouse Rentals in Oshawa?

    Enhance your stay in our Townhouse Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 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 $18 NZD 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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