Book Holiday Homes in Windsor
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Featured Holiday Homes in Windsor

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Charming 2-bedroom house close to airport and downtown with many amenities

Amazing townhouse, amazing attractions, amazing city!

Two bedroom suite with city views in the heart of downtown Madison

One Bedroom King with Den with views of the heart of downtown.

A Pleasant Retreat- No Cleaning Fee & New Discounts

Paoli Den - Newly Remodeled!

Studio queen with views of Lake Monona in the heart of downtown Madison

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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 | 117 Holiday Homes |
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Lowest Price | AU$100 |
Highest Price | AU$915 |
Popular accommodation | One Bedroom King with Den with views of Lake Monona in the heart of downtown., Charming 2-bedroom house close to airport and downtown with many amenities, Amazing townhouse, amazing attractions, amazing city!, Two bedroom suite with city views in the heart of downtown Madison, One Bedroom King with Den with views of the heart of downtown., A Pleasant Retreat- No Cleaning Fee & New Discounts, Paoli Den - Newly Remodeled!, Studio queen with views of Lake Monona in the heart of downtown Madison, Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown! |
Holiday Homes in Windsor
Top Locations for Holiday Homes in Windsor
More accommodations in Windsor
Top trending hotels in Windsor

Days Inn by Wyndham Madison NE/Windsor

The Madison Concourse Hotel and Governor's Club

Baymont by Wyndham Madison West/Middleton WI West

Moxy Madison Downtown
More ways to explore Windsor
Top picks
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^Subject to availability and chosen travel dates.