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Compare 66 Vacation Homes in Windsor with updated reviews, rates, and availability.

Amazing townhouse, amazing attractions, amazing city!
Space for everyone!
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Property grounds
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (80)
"Everything was absolutely great! Location was perfect, lots of good restaurants and shopping near the house. Beautiful scenery and tranquil setting for relaxing. House was just as advertised and had everything we needed. Hosts are amazing and so kind! You’ll love the visits from their pups! Highly recommend!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
A Pleasant Retreat- No Cleaning Fee & New Discounts
Living Room
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (187)
"We loved this house and the gardens! It is ideally located, a quick walk into town. The Frank Lloyd Wright accents compliment the furnishings and decor of the house to a tee. It is well-stocked with everything you need! Connie and Randy (the owners) are delightful. We will definitely stay here again when the opportunity arises."
A Pleasant Retreat- No Cleaning Fee & New Discounts
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Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Dining
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (18)
"This is our second visit to the property and are pleased to say high standards have been maintained. The property is comfortable and very clean. We also like the location. Would certainly return."
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Country setting
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (132)
"We loved our stay. The house was comfortable and clean. It had all the amenities. The location was spectacular, and the backyard was super peaceful. Joan was a great host and communication was easy. There are three bedrooms for six people and a full-size futon, which is great for our group of 6."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Two bedroom suite with city views in the heart of downtown Madison
Living area
Two bedroom suite with city views in the heart of downtown Madison
10.0 out of 10, Exceptional, (2)
"We enjoyed our stay at the Saddlery! The 2 bedroom suite was beautiful with plenty of room to relax. The building has a lovely exterior deck to sit and enjoy the view of Lake Monona. The location is great- a short walk to the capitol and its surrounding attractions. We would definitely stay there again!"
The price is AED 1,576
AED 2,037 total
includes taxes & fees
30 Jun - 1 Jul
Two bedroom suite with city views in the heart of downtown Madison
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
Interior
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
9.8 out of 10, Exceptional, (60)
"It was a perfect house for our group and we had a great weekend enjoying everything it had to offer!"
The price is AED 3,122
AED 4,934 total
includes taxes & fees
2 Jun - 3 Jun
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
Waterfront w/ HOT TUB + King Suite + Game Room
In the winter, the canal doesn't freeze over, but you can access the frozen lake directly just one block away for ice fishing. When it's warm enough, fish off the dock, take a swim, or watch the sunset with an old fashioned :) I
Waterfront w/ HOT TUB + King Suite + Game Room
9.2 out of 10, Wonderful, (15)
"St pattys fun with friends and family"
The price is AED 2,310
AED 4,657 total
includes taxes & fees
9 Jun - 10 Jun
Waterfront w/ HOT TUB + King Suite + Game Room
Paoli Den - Newly Remodeled!
Dining
Paoli Den - Newly Remodeled!
Paoli Den - Newly Remodeled!
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
8 person hot tub. Open all year round.
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
10.0 out of 10, Exceptional, (13)
"We stayed the weekend to watch our son play baseball against University of Wisconsin. Go Illini!! We also celebrated his 21st birthday with 3 other families. The house was clean and had plenty of space for everyone to sleep comfortably. We would definitely rent this house again."
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Interior
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
10.0 out of 10, Exceptional, (13)
"We loved our visit to Madison, made even more special with our stay in this awesome retro house! All of the special touches throughout the house were amazing, we would definitely stay here again in the future."
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Waters Edge Private Cottage
Property grounds
Waters Edge Private Cottage
7.4 out of 10, Good, (3)
"Won $500 pull tab this weekend. Would stay again."
The price is AED 709
AED 1,590 total
includes taxes & fees
2 Jun - 3 Jun
Waters Edge Private Cottage
HOT TUB - Game Room - Pond - King Suite - Fire Pit
30x15 main level living room with wood burning fire place, shuffleboard table, 65" smart TV, and walkout sliding door to the deck.
HOT TUB - Game Room - Pond - King Suite - Fire Pit
The price is AED 1,076
AED 2,487 total
includes taxes & fees
3 Jun - 4 Jun
HOT TUB - Game Room - Pond - King Suite - Fire Pit
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
Private kitchen
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
9.0 out of 10, Wonderful, (7)
"There is more than enough beds for a group of 10 to have their own beds. The town is nice and quiet and it’s a 30 second walk to the nearest bar. We never felt on top of each other and were really comfortable in the house. I would go back!"
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Outdoor dining
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
10.0 out of 10, Exceptional, (18)
"Everything about our stay was fantastic! The house was nicely decorated and extremely clean. The kitchen was well appointed and had everything we needed. Beds were comfy. Shower was great. A perfect place for our group of friends to spend a long weekend. I wouldn’t hesitate to stay here again!"
The price is AED 989
AED 1,990 total
includes taxes & fees
24 Jun - 25 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Conveniently Located just off University Avenue on Madison's West Side
Exterior
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (108)
"huge property lots of open outdoor area, lots of indoor space. Excellent host."
Conveniently Located just off University Avenue on Madison's West Side
Wisconsin River Valley Farmhouse w/Fire Pit & View
Portage Vacation Rental | 4BR | 1.5BA | 1,600 Sq Ft | Stairs Required
Wisconsin River Valley Farmhouse w/Fire Pit & View
10.0 out of 10, Exceptional, (38)
"This house was super awesome. We came up from Ohio and the the house and owners had everything we could’ve needed and more! The land was beautiful! Only complaint was no porch light on the front of the house so we kept passing it at night time. Would recommend and would stay again!"
Wisconsin River Valley Farmhouse w/Fire Pit & View
Renovated home with lake views - near Ferry, Devil's Lake, and WI Dells!
Stairs required to enter the home
Renovated home with lake views - near Ferry, Devil's Lake, and WI Dells!
10.0 out of 10, Exceptional, (24)
"We have been to many rental properties. This by far was the cleanest we have ever been to. The space was comfortable and simple to make it feel cozy. Location made it convenient to all the attraction around. We would definitely stay again!"
The price is AED 657
AED 1,219 total
includes taxes & fees
9 Jun - 10 Jun
Renovated home with lake views - near Ferry, Devil's Lake, and WI Dells!
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Private kitchen
Two Bedroom with views of Lake Monona in the heart of downtown Madison
The price is AED 2,016
AED 2,615 total
includes taxes & fees
30 Jun - 1 Jul
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Waterfront Lodi Vacation Rental on Lake Wisconsin!
Lodi Vacation Rental | 3BR | 2BA | 1,000 Sq Ft | 1 Step Required
Waterfront Lodi Vacation Rental on Lake Wisconsin!
10.0 out of 10, Exceptional, (4)
"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!
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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.

Other property types in Windsor

Enjoy Nature with Full Comfort!
Room
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"Space is clean, property is very pretty! Pool wasn’t ready for use, but can imagine it would add even more to the a summer stay! Owner is easy to communicate with. Ran into severe weather - owners were welcoming and ensured we were safe at all times. We will definitely be back to visit again!"
The price is AED 331
AED 504 total
includes taxes & fees
6 Jun - 7 Jun
Enjoy Nature with Full Comfort!
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
Interior
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
9.8 out of 10, Exceptional, (60)
"It was a perfect house for our group and we had a great weekend enjoying everything it had to offer!"
The price is AED 3,122
AED 4,934 total
includes taxes & fees
2 Jun - 3 Jun
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
Lodi Vacation Rental | 2BR | 2BA | 1,300 Sq Ft | Stairs Required for Access
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
10.0 out of 10, Exceptional, (36)
"We had a great time! House was so clean and stocked with everything we needed. Would definitely stay again. Just adorable! I would recommend cutting the grass and storing your wood in a sheltered area. The wood was too wet to use-we had to purchase some & the grass was long with prickly vines on the stairs. The grass was long around the BBQ."
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
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.

Recent reviews of Windsor hotels
Expedia verified reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

5/5 Excellent
"Rooms are clean and updated. Wonderful view of the Capitol building. We walked to the Saturday am Farmers market. "
A verified traveler from Huntsville stayed at The Madison Concourse Hotel and Governor's Club
Posted 2 days ago
The Madison Concourse Hotel and Governor's Club