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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windsor Vacation Homes

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

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

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is CA $384
CA $507 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
ONE OF A KIND vacation rental with a view
Exterior

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view
Waterfront Lodi Vacation Rental on Lake Wisconsin!
Outdoor dining

Waterfront Lodi Vacation Rental on Lake Wisconsin!

10.0 out of 10, Exceptional, (14)
"Very clean! Awesome accommodations! Perfect couple of nights on the lake - kids even jumped in in early May! Washer/dryer is always an added bonus. Coffee bar a nice touch, and the kids loved the lanterns : )"
Waterfront Lodi Vacation Rental on Lake Wisconsin!
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Interior

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is CA $480
CA $634 total
includes taxes & fees
Sep 1 - Sep 2
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (1)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
Private Pool - HOT TUB - Sauna - Game Room - Pets
Two bedroom suite with city views in the heart of downtown Madison
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (33)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is CA $453
CA $598 total
includes taxes & fees
Sep 1 - Sep 2
Two bedroom suite with city views in the heart of downtown Madison
One Bedroom King with Den with views of the heart of downtown.
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is CA $370
CA $489 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with Den with views of the heart of downtown.
Doty ★ Walk to Everything -Hotel Quality- Downtown
Fridge, microwave, oven, stovetop

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (23)
"Prefect"
Paoli Den - Newly Remodeled!
Escape to tranquility – your countryside haven, and at times with a horse or two
Outdoor dining

Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Plan your reunion/gathering now in beautiful rural South Central Wisconsin
Exterior

Plan your reunion/gathering now in beautiful rural South Central Wisconsin

10.0 out of 10, Exceptional, (162)
"Oak House is a unique property ideally suited for family gatherings - this was our fourth stay. The house is roomy, well appointed, and decorated for the holidays. It also has access to nature trails for daily walks. The location has quiet privacy with quick access to activities in Madison. The property manager Rachel is very responsive. We highly recommend a stay here. "
Plan your reunion/gathering now in beautiful rural South Central Wisconsin
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
3 bedrooms, desk, free WiFi

Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

10.0 out of 10, Exceptional, (33)
"We had a great time being close to the lake. Everything in the house was very charming and comfortable. Would stay again for sure!"
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Premium 3BR | Quick to Downtown
Fridge, microwave, oven, stovetop

Premium 3BR | Quick to Downtown

10.0 out of 10, Exceptional, (10)
"Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive."
The price is CA $453
CA $1,096 total
includes taxes & fees
Aug 11 - Aug 12
Premium 3BR | Quick to Downtown
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Interior

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

10.0 out of 10, Exceptional, (5)
The price is CA $454
CA $796 total
includes taxes & fees
Aug 12 - Aug 13
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
King Suite - Game Room - Large Groups - Yard
Fridge, microwave, oven, stovetop

King Suite - Game Room - Large Groups - Yard

10.0 out of 10, Exceptional, (9)
"Our family enjoyed our stay in Madison. The house was great and our host was very responsive. I would highly recommend this duplex for your trip. "
King Suite - Game Room - Large Groups - Yard
Beautifully remodeled 2 bed 104 Berkley Verona #6
Exterior

Beautifully remodeled 2 bed 104 Berkley Verona #6

9.6 out of 10, Exceptional, (24)
"The apartment is well maintained and Joel was helpful. We’d stay again if we need a place to stay in Verona"
Beautifully remodeled 2 bed 104 Berkley Verona #6
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Smart TV, music library, stereo

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (89)
"Such a charming spot right on the lake! Direct access to the water, beautiful views, close to a bunch of fun bars and restaurants, and an easy drive to Devil’s Lake, Wisconsin Dells, and Madison. We stayed for a long weekend with our six month old, and it was great! Joe, the owner, is so friendly and responsive. Highly recommended!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Studio queen with views of Lake Monona in the heart of downtown Madison
Exterior

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

9.4 out of 10, Exceptional, (9)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is CA $288
CA $380 total
includes taxes & fees
Sep 1 - Sep 2
Studio queen with views of Lake Monona in the heart of downtown Madison
One Bedroom King with views of the heart of downtown.
1 bedroom, WiFi

One Bedroom King with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (2)
"I loved the location and the area it was located. I really loved the view and the clearness of the place as well. It was very homey and cozy. "
The price is CA $343
CA $453 total
includes taxes & fees
Sep 1 - Sep 2
One Bedroom King with views of the heart of downtown.
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Interior

Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

8.6 out of 10, Excellent, (16)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
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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Top Windsor Hotel Reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"The most comfortable beds EVER. I even took a picture of the tags so I can get the same exact one! Love this hotel! My rant has stayed there at least 10 times and will keep coming back!"
Stephanie 2-night trip
Posted 14 hours ago
The Madison Concourse Hotel and Governor's Club