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.

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

Madison
The price is AU$487 per night from 1 Apr to 2 Apr
AU$487
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home, you'll be centrally located in Madison, a 3-minute drive from University of Wisconsin-Madison and 5 minutes from Camp Randall ...
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

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

Madison
The price is AU$367 per night from 1 Apr to 2 Apr
AU$367
includes taxes & fees
1 Apr - 2 Apr
Located in Madison, this vacation home is within a 15-minute drive of University of Wisconsin-Madison and Camp Randall Stadium.
Charming 2-bedroom house close to airport and downtown with many amenities
Amazing townhouse, amazing attractions, amazing city!

Amazing townhouse, amazing attractions, amazing city!

Monona
With a stay at this vacation home in Madison (Monona), you'll be within a 10-minute drive of University of Wisconsin-Madison and Alliant Energy Center.
Amazing townhouse, amazing attractions, amazing city!
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Two bedroom suite with city views  in the heart of downtown Madison

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

Madison
The price is AU$592 per night from 1 Apr to 2 Apr
AU$592
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home, you'll be centrally located in Madison, a 3-minute drive from University of Wisconsin-Madison and 5 minutes from Camp Randall ...
Two bedroom suite with city views in the heart of downtown Madison
One Bedroom King with Den with views of the heart of downtown.

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

2 out of 5
Madison
The price is AU$466 per night from 1 Apr to 2 Apr
AU$466
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home, you'll be centrally located in Madison, a 3-minute drive from University of Wisconsin-Madison and 5 minutes from Camp Randall ...
One Bedroom King with Den with views of the heart of downtown.
A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts

Sun Prairie
With a stay at this vacation home in Sun Prairie, you'll be within a 10-minute walk of Sun Prairie Historical Library and Museum and Angell Park Speedway.
A Pleasant Retreat- No Cleaning Fee & New Discounts
Paoli Den - Newly Remodeled!

Paoli Den - Newly Remodeled!

Verona
Located in Verona, this vacation home is within a 5-minute drive of Fireman's Beach and Verona Ice Arena.
Paoli Den - Newly Remodeled!
Studio queen with views of Lake Monona in the heart of downtown Madison

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

Madison
The price is AU$338 per night from 1 Apr to 2 Apr
AU$338
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home, you'll be centrally located in Madison, a 3-minute drive from University of Wisconsin-Madison and 5 minutes from Camp Randall ...
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!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Monona
The price is AU$915 per night from 6 Apr to 7 Apr
AU$915
includes taxes & fees
6 Apr - 7 Apr
Located in Madison (Monona), this vacation home is within a 10-minute drive of University of Wisconsin-Madison and Alliant Energy Center.
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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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.

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
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!

Top trending hotels in Windsor

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr, I-90/94 and Hwy 19, Windsor, WI
Fully refundableReserve now, pay when you stay
The price is AU$100 per night from 6 Apr to 7 Apr
AU$100
includes taxes & fees
6 Apr - 7 Apr
Located in Windsor, Days Inn by Wyndham Madison NE/Windsor is within a 10-minute drive of East Towne Mall and Madison Area Technical College.
Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$274 per night from 1 Apr to 2 Apr
AU$274
includes taxes & fees
1 Apr - 2 Apr
With a stay at The Madison Concourse Hotel and Governor's Club, you'll be centrally located in Madison, within a 5-minute drive of University of Wisconsin-Madison ...
The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$111 per night from 19 Apr to 20 Apr
AU$111
includes taxes & fees
19 Apr - 20 Apr
When you stay at Baymont by Wyndham Madison West/Middleton WI West in Madison, you'll be near the airport, within a 15-minute drive of University of Wisconsin-Madison ...
Baymont by Wyndham Madison West/Middleton WI West
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Moxy Madison Downtown

Moxy Madison Downtown

3.5 out of 5
823 East Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is AU$213 per night from 6 Apr to 7 Apr
AU$213
includes taxes & fees
6 Apr - 7 Apr
With a stay at Moxy Madison Downtown, you'll be centrally located in Madison, a 4-minute drive from University of Wisconsin-Madison and 6 minutes from Camp Randall ...
Moxy Madison Downtown
Don't see what you're looking for?
See all available properties in Windsor
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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.