Photo by Joel Holland

Search Vacation Homes in Windsor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Vacation Homes in Windsor

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, (29)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is AED 1,282
AED 1,693 total
includes taxes & fees
20 Jul - 21 Jul
Two bedroom suite with city views in the heart of downtown Madison
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, (5)
"We loved everything about this property. Would definitely stay there again."
The price is AED 1,355
AED 1,790 total
includes taxes & fees
22 Jul - 23 Jul
Two Bedroom with views of Lake Monona in the heart of downtown Madison
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, (115)
"I was visiting from Chicago for a concert and was immediately sold with this property! I loved the hot tub and fireplace!! The whole house was clean and very bright! I will definitely stay again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

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

Private Pool - HOT TUB - Sauna - Game Room - Pets
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, (21)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is AED 1,098
AED 1,451 total
includes taxes & fees
20 Jul - 21 Jul
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, (138)
"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
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (19)
"We were in town for a wedding, and this was the perfect place for us and our two young children. The space was very clean and had everything we needed for our stay. The host was extremely friendly and helpful and was quick to respond to any messages. We would definitely recommend! "
Paoli Den - Newly Remodeled!
A Pleasant Retreat- No Cleaning Fee & New Discounts
Property grounds

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (240)
"Very comfortable and clean. 2 adults and 2 children had plenty of room to play and relax Location was easy to get to and easy to get around to places we wanted to visit in Madison "
A Pleasant Retreat- No Cleaning Fee & New Discounts
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
9.6 out of 10, Exceptional, (17)
"Great stay, easy location."
The price is AED 1,062
AED 1,404 total
includes taxes & fees
21 Jul - 22 Jul
One Bedroom King with Den with views of the heart of downtown.
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, (85)
"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 !!
Original cozy farmhouse homestead 2 blocks from the bike path and
Terrace/patio

Original cozy farmhouse homestead 2 blocks from the bike path and

10.0 out of 10, Exceptional, (114)
"Great house and location. Check in and out was easy and our host was very gracious. "
Original cozy farmhouse homestead 2 blocks from the bike path and
King Suite - Game Room - Large Groups - Yard
Fridge, microwave, oven, stovetop

King Suite - Game Room - Large Groups - Yard

10.0 out of 10, Exceptional, (8)
"The house was spotlessly clean and spacious. Easy to get to Madison and also lots to do in Sun Prairie. "
King Suite - Game Room - Large Groups - Yard
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, (21)
"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
Nature's Haven, near Madison-pet friendly!
Dining

Nature's Haven, near Madison-pet friendly!

10.0 out of 10, Exceptional, (2)
"The small cottage in the woods with nice yard and amenities for our little family."
Nature's Haven, near Madison-pet friendly!
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, (8)
"We had no issues with our stay and really enjoyed the unit we booked. "
The price is AED 841
AED 1,112 total
includes taxes & fees
27 Jul - 28 Jul
Studio queen with views of Lake Monona in the heart of downtown Madison
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, (32)
"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
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, (6)
"Excellent"
Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic
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, (18)
"As Advertised, beautiful property, great little beach for kids!"
Tranquil Lakefront Retreat with Breathtaking Views and Cozy Firepit
Waterfront Lodi Vacation Rental on Lake Wisconsin!
Outdoor dining

Waterfront Lodi Vacation Rental on Lake Wisconsin!

10.0 out of 10, Exceptional, (11)
"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!
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, (38)
"We enjoyed our stay!"
The price is AED 904
AED 1,889 total
includes taxes & fees
31 Jul - 1 Aug
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

10/10 Excellent
"It is one of my favorites spots "
Delores 1-night trip
Posted 16 hours ago
Motel 6 Madison, WI - East