Book Holiday Homes in Oshawa

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Featured Holiday Homes in Oshawa

Cozy Pickering Lakeside Home

Cozy Pickering Lakeside Home

Pickering
Located in Pickering, this vacation home is within a 15-minute drive of Toronto Zoo and Scarborough Town Centre.
Cozy Pickering Lakeside Home
Newly Renovated Home in Whitby

Newly Renovated Home in Whitby

Whitby
The price is AU$698 per night from 24 Dec to 25 Dec
AU$698
includes taxes & fees
24 Dec - 25 Dec
Located in Whitby, this vacation home is a 4-minute drive from Deer Creek North Golf Course and 6 minutes from Luke Andrews Wood Sculptures.
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 AU$1,454 per night from 24 Dec to 25 Dec
AU$1,454
includes taxes & fees
24 Dec - 25 Dec
With a stay at this vacation home in Ajax, you'll be within a 15-minute drive of Toronto Zoo and Rouge National Urban Park.
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 AU$636 per night from 12 Jan to 13 Jan
AU$636
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at this vacation home in Whitby, you'll be within a 5-minute drive of 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
A stay at this vacation home places you in the heart of Ajax, within a 5-minute drive of Lake Ontario and Ajax Convention Centre.
Beautiful New Townhouse in Quiet Neighbourhood
Luxury Waterfront Bowmanville getaway home!

Luxury Waterfront Bowmanville getaway home!

Bowmanville
The price is AU$723 per night from 27 Dec to 28 Dec
AU$723
includes taxes & fees
27 Dec - 28 Dec
With a stay at this vacation home in Clarington, you'll be on the waterfront, just steps from Lake Ontario and a 3-minute drive from Dave Boyd Memorial Dog ...
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
Located in Ajax, this vacation home is a 4-minute drive from Ajax Convention Centre and 6 minutes from Veterans' Point Gardens.
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
Located in Oshawa (Samac), this vacation home is within a 5-minute drive of Ontario Tech University and Neb's Funworld.
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
With a stay at this vacation home in Ajax, you'll be within a 15-minute drive of Toronto Zoo and Ajax Convention Centre.
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
AU$129
Highest Price
AU$1,454
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 AU$169 per night from 19 Jan to 20 Jan
AU$169
includes taxes & fees
19 Jan - 20 Jan 2025
With a stay at La Quinta Inn & Suites by Wyndham Oshawa, you'll be centrally located in Oshawa, just a 2-minute walk from Tribute Communities Centre and 6 minutes ...
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
Located in Oshawa (Vanier), Travelodge by Wyndham Oshawa Whitby is within a 5-minute drive of Oshawa Centre and Lynde Shores Conservation Area.
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 AU$129 per night from 5 Jan to 6 Jan
AU$129
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at Comfort Inn Oshawa places you in the heart of Oshawa, within a 5-minute drive of Oshawa Centre and Lynde Shores Conservation Area.
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 AU$178 per night from 25 Dec to 26 Dec
AU$178
includes taxes & fees
25 Dec - 26 Dec
With a stay at Holiday Inn Express & Suites Oshawa Downtown - Toronto Area, an IHG Hotel, you'll be centrally located in Oshawa, within a 10-minute walk of Canadian ...
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.

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^Subject to availability and chosen travel dates.