Book Holiday Homes in Oshawa

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Featured Holiday Homes in Oshawa

Cozy Pickering Lakeside Home

Cozy Pickering Lakeside Home

Pickering
Stay at this vacation home in Pickering. Enjoy air conditioning. Popular attractions Toronto Zoo and Millennium Square are located nearby.
Cozy Pickering Lakeside Home
Newly Renovated Home in Whitby

Newly Renovated Home in Whitby

Whitby
The price is NZ$764 per night from 24 Dec to 25 Dec
NZ$764
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Whitby. Enjoy a garden, a pool table, and patios. Popular attractions Deer Creek North Golf Course and Royal Ashburn Golf Club ...
Newly Renovated Home in Whitby
3 Bedroom + 4 Washroom Cottage Home on a Large Private Lot Surrounded by Trees

3 Bedroom + 4 Washroom Cottage Home on a Large Private Lot Surrounded by Trees

Ajax
The price is NZ$1,590 per night from 1 Jan to 2 Jan
NZ$1,590
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this vacation home in Ajax. Enjoy free WiFi, in-room fireplaces, and air conditioning. Popular attractions Pickering Casino Resort and Deer Creek North ...
3 Bedroom + 4 Washroom Cottage Home on a Large Private Lot Surrounded by Trees
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White House - 4 Bedroom Home

White House - 4 Bedroom Home

Whitby
The price is NZ$698 per night from 12 Jan to 13 Jan
NZ$698
includes taxes & fees
12 Jan - 13 Jan 2025
Stay at this vacation home in Whitby. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Lynde Shores Conservation Area and Oshawa Centre ...
White House - 4 Bedroom Home
Beautiful New Townhouse in Quiet Neighbourhood

Beautiful New Townhouse in Quiet Neighbourhood

Ajax
Stay at this vacation home in Ajax. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Veterans' Point Gardens ...
Beautiful New Townhouse in Quiet Neighbourhood
Luxury Waterfront Bowmanville getaway home!

Luxury Waterfront Bowmanville getaway home!

Bowmanville
The price is NZ$791 per night from 27 Dec to 28 Dec
NZ$791
includes taxes & fees
27 Dec - 28 Dec
Stay at this vacation home in Clarington. Enjoy a garden, a pool table, and balconies. Popular attractions Country Chic Shabby Chic & All Things Country and ...
Luxury Waterfront Bowmanville getaway home!
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking

Ajax
Stay at this vacation home in Ajax. Enjoy air conditioning. Popular attractions Pickering Casino Resort and Veterans' Point Gardens are located nearby.
GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking
Newly Built Modern 4BR 2.5Bath Townhouse Free Parking Amazing view!Entire house

Newly Built Modern 4BR 2.5Bath Townhouse Free Parking Amazing view!Entire house

Oshawa
Stay at this vacation home in Oshawa. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Neb's Funworld and Ontario Regiment Museum are ...
Newly Built Modern 4BR 2.5Bath Townhouse Free Parking Amazing view!Entire house
Modern bright cozy 3bed 3bath Vacation house in Ajax, GTA, ON, Canada

Modern bright cozy 3bed 3bath Vacation house in Ajax, GTA, ON, Canada

Ajax
Stay at this vacation home in Ajax. Enjoy free WiFi, a water park, and Netflix. Popular attractions Pickering Casino Resort and Veterans' Point Gardens are located ...
Modern bright cozy 3bed 3bath Vacation house in Ajax, GTA, ON, Canada
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oshawa Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oshawa vacation homes are the perfect way for you to wing it.

Holiday houses in Oshawa let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oshawa in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oshawa adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oshawa with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oshawa vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oshawa Holiday Homes essential information

Accommodation
189 Holiday Homes
Lowest Price
NZ$143
Highest Price
NZ$1,590
Popular accommodation
Cozy Pickering Lakeside Home, Newly Renovated Home in Whitby , 3 Bedroom + 4 Washroom Cottage Home on a Large Private Lot Surrounded by Trees, White House - 4 Bedroom Home , Beautiful New Townhouse in Quiet Neighbourhood, Luxury Waterfront Bowmanville getaway home!, GORGEOUS 1 BDR PRIME KITCHEN No sharing spaces/ WIFI+ Parking, Newly Built Modern 4BR 2.5Bath Townhouse Free Parking Amazing view!Entire house , Modern bright cozy 3bed 3bath Vacation house in Ajax, GTA, ON, Canada

Top trending hotels in Oshawa

La Quinta Inn & Suites by Wyndham Oshawa

La Quinta Inn & Suites by Wyndham Oshawa

2.5 out of 5
63 King Street East, A, Oshawa, ON
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 5 Jan to 6 Jan
NZ$218
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Oshawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Oshawa
Travelodge by Wyndham Oshawa Whitby

Travelodge by Wyndham Oshawa Whitby

2 out of 5
940 Champlain Avenue, Oshawa, ON
Book a stay at this business-friendly hotel in Oshawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
Travelodge by Wyndham Oshawa Whitby
Comfort Inn Oshawa

Comfort Inn Oshawa

2.5 out of 5
605 Bloor St W, Oshawa, ON
Fully refundableReserve now, pay when you stay
The price is NZ$143 per night from 5 Jan to 6 Jan
NZ$143
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this hotel in Oshawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oshawa ...
Comfort Inn Oshawa
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Holiday Inn Express & Suites Oshawa Downtown - Toronto Area, an IHG Hotel

Holiday Inn Express & Suites Oshawa Downtown - Toronto Area, an IHG Hotel

2.5 out of 5
67 Simcoe Street North, Oshawa, ON
Fully refundable
The price is NZ$197 per night from 25 Dec to 26 Dec
NZ$197
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this business-friendly hotel in Oshawa. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Holiday Inn Express & Suites Oshawa Downtown - Toronto Area, an IHG Hotel
Don't see what you're looking for?
See all available properties in Oshawa
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.