Book Holiday Homes in Windsor

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Windsor 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 Windsor vacation homes are the perfect way for you to wing it.

Holiday houses in Windsor 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 Windsor 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 Windsor adventures, obvs.

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

Windsor Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$127
Highest Price
AU$197
Popular accommodation
Norfolk Waterside Marriott, Embassy Suites by Hilton Hampton Convention Center, Comfort Inn Newport News - Hampton I-64, Comfort Inn & Suites Hampton near Coliseum

Top trending hotels in Windsor

Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 24 Dec to 25 Dec
AU$197
24 Dec - 25 Dec
includes taxes & fees
Norfolk Waterside Marriott is centrally located in Norfolk, a 2-minute walk from Waterside District and 15 minutes by foot from Harbor Park.
Opens in a new windowNorfolk Waterside Marriott
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 21 Dec to 22 Dec
AU$158
21 Dec - 22 Dec
includes taxes & fees
With a stay at Embassy Suites by Hilton Hampton Convention Center, you'll be centrally located in Hampton, a 2-minute drive from Hampton Coliseum and 7 minutes ...
Opens in a new windowEmbassy Suites by Hilton Hampton Convention Center
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave Newport News VA
The price is AU$127 per night from 25 Dec to 26 Dec
AU$127
25 Dec - 26 Dec
includes taxes & fees
With a stay at Comfort Inn Newport News - Hampton I-64 in Newport News (Central Newport News), you'll be within a 15-minute drive of Hampton Coliseum and Langley ...
Opens in a new windowComfort Inn Newport News - Hampton I-64
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Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 18 Jan to 19 Jan
AU$143
18 Jan - 19 Jan 2026
includes taxes & fees
With a stay at Comfort Inn & Suites Hampton near Coliseum, you'll be centrally located in Hampton, a 5-minute drive from Langley Air Force Base and 5 minutes ...
Opens in a new windowComfort Inn & Suites Hampton near Coliseum
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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.