Photo by Joel Holland

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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Vacation Homes in Windsor

Our top choices for Windsor vacation homes

A Pleasant Retreat- No Cleaning Fee & New Discounts
Property grounds

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (248)
"Host was easy to communicate with and it was an overall a fantastic experience. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (25)
"Prefect"
Paoli Den - Newly Remodeled!
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, (93)
"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 !!
Updated home w/ lake views across from Lake WI!
Fridge, microwave, oven, stovetop

Updated home w/ lake views across from Lake WI!

10.0 out of 10, Exceptional, (30)
"Very clean great place. Beautiful location"
Updated home w/ lake views across from Lake WI!
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Exterior

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

9.8 out of 10, Exceptional, (42)
"Such a nice house! Great location and excellent amenities!"
The price is SAR 896
SAR 1,868 total
includes taxes & fees
8 Sep - 9 Sep
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to 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, (142)
"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
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Outdoor spa tub

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (116)
"My husband and I live hear Chicago and wanted a quick getaway and this beautiful apartment felt like a home away from home. The hosts thought of every detail when designing this fun and very functional space (even the shower soap was a special luxury!) The bed was incredibly comfortable and the fireplace added warmth and coziness. We would love to stay here again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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
On the Yahara River, access to Madison Lakes
Exterior

On the Yahara River, access to Madison Lakes

10.0 out of 10, Exceptional, (42)
"Beautiful home in a great setting. Really enjoyed our stay. "
On the Yahara River, access to Madison Lakes
Brand New Country Rustic Barn-R&R At It's Finest! Madison Area
Fridge, microwave, oven, stovetop

Brand New Country Rustic Barn-R&R At It's Finest! Madison Area

9.8 out of 10, Exceptional, (22)
"It was great, good location near Madison for local dining.Loved the special touches, Christmas tree, dog bed, dog water bowls, rustic theme.Solo stove and stuff to make smores"
Brand New Country Rustic Barn-R&R At It's Finest! Madison Area
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
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!"
The price is SAR 925
SAR 1,472 total
includes taxes & fees
10 Sep - 11 Sep
Doty ★ Walk to Everything -Hotel Quality- Downtown
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Interior

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

8.2 out of 10, Very Good, (20)
"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!
One Bedroom Queen in the heart of downtown.
Private kitchen

One Bedroom Queen in the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay and the close location to the capital. Great modern style and very functional "
One Bedroom Queen in the heart of downtown.
Tranquil Lakefront Retreat with Breathtaking Views and Cozy Firepit
Fridge, microwave, oven, stovetop

Tranquil Lakefront Retreat with Breathtaking Views and Cozy Firepit

2.0 star property
9.8 out of 10, Exceptional, (19)
"As Advertised, beautiful property, great little beach for kids!"
Tranquil Lakefront Retreat with Breathtaking Views and Cozy Firepit
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, (36)
"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
Amazing townhouse, amazing attractions, amazing city!
Fridge, microwave, oven, stovetop

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (180)
"Everything was very clean, amenities were awesome and overall we had a great time! "
Amazing townhouse, amazing attractions, amazing city!
Updated 3 bed + office ranch home close to Downtown Madison
Outdoor dining

Updated 3 bed + office ranch home close to Downtown Madison

10.0 out of 10, Exceptional, (18)
"We stayed here and used it as a Homebase to visit family and explore the Madison area. It was very clean, had everything we needed, and looked just like the pictures. Will definitely stay here again in the future!"
Updated 3 bed + office ranch home close to Downtown Madison
Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic
Terrace/patio

Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic

10.0 out of 10, Exceptional, (8)
"Host was very accommodating! Home is cozy and comfortable felt like home. Thank you again for opening your home and giving us a place to stay! "
Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
Terrace/patio

Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

10.0 out of 10, Exceptional, (21)
"We coordinated with John and Maria for a family event for the weekend and they were obliging for all our needs!"
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
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 drawers for clothing drifted open on their own, but when I told the front desk about that they said they would address it. I’m confident that they have. I left an expensive item there and they contacted me immediately to mail it back to me. The woman at check-in Was very difficult to understand which made things awkward and take a long time. I’m sorry if that sounds bad. All other staff and service was perfect. I love this hotel."
Jennifer 2-night trip
Posted 3 days ago
The Madison Concourse Hotel and Governor's Club
Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

10/10 Excellent
"It was a nice stay"
Sascha 1-night trip
Posted 7 days ago
Baymont Inn & Suites by Wyndham Madison