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Compare 88 Vacation Homes in Windsor with updated reviews, rates, and availability.

A Pleasant Retreat- No Cleaning Fee & New Discounts
Street view of front yard

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (220)
"We stayed two nights on a weekend to celebrate with family and our college graduate. We had 7 stay comfortably using the sunroom bed. The house was amazing and had everything we needed throughout the weekend. The backyard is very nice. We really loved everything about the house. The hosts were excellent, very helpful and extremely easy to communicate with. The neighborhood is very quiet and the location gives easy access to Madison. An amazing weekend! We would highly recommend!"
The price is AED 826
AED 1,058 total
includes taxes & fees
5 Jan - 6 January 2025
A Pleasant Retreat- No Cleaning Fee & New Discounts
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, (99)
"Exquisitely laid out and decorated to blend perfectly with nature’s beauty. Attention to detail and wonderful amenities. You will not be disappointed with this cozy private retreat!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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!

9.8 out of 10, Exceptional, (31)
"Jake’s place was perfect for our stay, as it was a relaxing, clean and a nice home. The two floor layout worked especially well for our infant daughter so she had a quiet place to sleep, while we could cook and hang out in the living room. The only suggestion to the host is to install curtains along the picturesque sliding doors for a bit of extra privacy at nighttime."
The price is AED 937
AED 1,905 total
includes taxes & fees
1 Jan - 2 January 2025
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Living area

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

10.0 out of 10, Exceptional, (25)
"We were celebrating our son's graduation. This was a perfect spot and couldn't be happier with our selection. We will definitely stay here again if the need arises. "
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Two bedroom suite with city views in the heart of downtown Madison
Private kitchen

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

10.0 out of 10, Exceptional, (14)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is AED 1,025
AED 1,327 total
includes taxes & fees
26 Dec - 27 Dec
Two bedroom suite with city views in the heart of downtown Madison
Studio queen with views of Lake Monona in the heart of downtown Madison
Living area

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

9.0 out of 10, Wonderful, (4)
"Was in town for UWM parents weekend and wanted something more than a simple hotel room as I was going to be there for nearly a week. The Saddlery for the bill. Location was amazing. Having a kitchenette meant I could fully enjoy the great farmers market that weekend. And the view out my window of the lake was a perfect way to wake up. Manager was very responsive. Everything was as stated. TV/media set up would benefit from updating, but it actually didn’t matter as it allowed me to tuck into a...
The price is AED 657
AED 851 total
includes taxes & fees
26 Dec - 27 Dec
Studio queen with views of Lake Monona in the heart of downtown Madison
Okee Bay House on Lake Wisconsin w/ Private Dock!
Lodi Vacation Rental | 4BR | 2BA | 1,500 Sq Ft | 1 Step to Enter

Okee Bay House on Lake Wisconsin w/ Private Dock!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a relaxing stay at this great lake house. The house is exactly as advertised, especially the access to the lake which is right in the backyard. Everything in the house is up to date with all you need for a group stay. We also enjoyed walking over to the nearby lakeside restaurants which have great seafood and live music. We would definitely return to this house."
Okee Bay House on Lake Wisconsin w/ Private Dock!
Madison Luxury Home With Hot Tub - 10 min to UW- Walk to lake Monona
Miscellaneous

Madison Luxury Home With Hot Tub - 10 min to UW- Walk to lake Monona

8.0 out of 10, Very Good, (2)
"Great property, great location. Very enjoyable stay."
The price is AED 767
AED 1,718 total
includes taxes & fees
9 Jan - 10 January 2025
Madison Luxury Home With Hot Tub - 10 min to UW- Walk to lake Monona
Wisconsin River Valley Farmhouse: Fire Pit & View
Portage Vacation Rental | 4BR | 1.5BA | 1,600 Sq Ft | Stairs Required

Wisconsin River Valley Farmhouse: Fire Pit & View

10.0 out of 10, Exceptional, (46)
"Great property, easy and easy out, loved that the dogs could be with us."
Wisconsin River Valley Farmhouse: Fire Pit & View
Home away from home!!!
Property grounds

Home away from home!!!

8.6 out of 10, Excellent, (11)
"This is a basement apartment in a gorgeous neighborhood. Took us about 25 minutes to get into the campus area, which we came to see. Great WiFi, we worked during tne day, house was quiet. Comfortable bed, sofa couch, and large bathroom. It was cool but there are portable heaters that were perfect. Close to a grocery store. Also, Gus’s Diner was minutes away and had very nice food. Great pizza close by too. House is next to an open space, saw cranes and goldfinches. Great place to stay. Hosts...
Home away from home!!!
Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!
Stairs required to enter the home

Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!

10.0 out of 10, Exceptional, (26)
"Perfect home base for a two-family vacay. Four teenage boys and two moms and we never felt crowded. Easy drive to the Dells, Devil’s Lake, and Baraboo. Beautiful views of Lake WI from the deck and a quick walk to fishing at Memorial park and ice cream at the ferry crossing. The house was very clean, stocked with basics, and communication with the owner was so easy. Highly recommend!"
Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!
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, (144)
"We have stayed multiple times, and always enjoy the country setting; cleanliness; well equipped, large kitchen; nearby dog park; and wonderful hosts. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Lake Monona Waterfront + HOT TUB + Game Room
The canal does not fully freeze in the winter, but if you walk 3 blocks down, you can access the frozen part of the lake for ice fishing.

Lake Monona Waterfront + HOT TUB + Game Room

9.6 out of 10, Exceptional, (27)
"Excellent location with beautiful view of the canal. Kids enjoyed watching the ducks and squirrels. Had everything we needed to enjoy our family quality time"
Lake Monona Waterfront + HOT TUB + Game Room
HOT TUB - 20 min to Capitol - KING Bed - Fireplace
Deck, hot tub, furniture, charcoal grill, fire pit, and games highlight our large back yard.

HOT TUB - 20 min to Capitol - KING Bed - Fireplace

9.8 out of 10, Exceptional, (6)
"My adult children (including SIL) and my partner and I wanted to visit Madison for the first time. While the house is a little further from downtown (20 mins.) than we might have liked, it was worth it for the size, comfort and cleanliness of the house. We had plenty of room and all of the necessities. We pretty much just slept and had breakfast at the house, but it would've been great if we'd needed to spend more time there. (I was looking forward to using the hot tub and Pacman machine,...
HOT TUB - 20 min to Capitol - KING Bed - Fireplace
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
Private kitchen

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

10.0 out of 10, Exceptional, (13)
"Everything is organized perfectly. Much thought has been put into making sure that guests are fully accommodated and comfortable. Beautiful extra touches left that show great consideration from the hosts! "
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
Family-Friendly Lake Waubesa Home: Boat + Swim!
McFarland Vacation Rental | 3BR | 3BA | Stairs Required | 1,794 Sq Ft

Family-Friendly Lake Waubesa Home: Boat + Swim!

9.8 out of 10, Exceptional, (9)
"Grandparents, parents, teen, college and young adult family members enjoyed the retro summer camp vibe in this historic house. The glassed in porch with fireplace was perfect for watching the lake and birds. Kitchen fully stocked for cooking our Thanksgiving meal. All bedrooms are on 2nd floor, with just one bathroom one each floor of the house...felt a little less private than we're used to, but the space overall felt so cozy and as if it was our own treasured family getaway...made up for any...
Family-Friendly Lake Waubesa Home: Boat + Swim!
ONE OF A KIND vacation rental with a view

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (130)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view
Paoli Den - Newly Remodeled!
Private kitchen

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (9)
"Everything we needed easy commute to city of wisconson, clean, great communication with the host and the host left a welcome basket for us that was focused towards the reason we were in town, world championship strongman competition. "
Paoli Den - Newly Remodeled!
Executive Retreat 6BR/2.5 Bath on 13 acres
Living area

Executive Retreat 6BR/2.5 Bath on 13 acres

10.0 out of 10, Exceptional, (1)
"The house is new and very clean. It is a nice private location. Multiple large bedrooms made it easy to accommodate multiple families nicely. They had the small things you tend to forget on hand and able to use. It was easy for a large group to gather and converse."
Executive Retreat 6BR/2.5 Bath on 13 acres
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
Private kitchen

Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!

8.8 out of 10, Excellent, (13)
"I loved the vibe of this house. So much character and nicely updated. We loved walking to the ferry, the ice cream stand, and taking a ride across the lake. It was the perfect stay for our weekend trip to Baraboo and Devil’s Lake. "
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
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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Other property types in Windsor

A Pleasant Retreat- No Cleaning Fee & New Discounts
Street view of front yard

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (220)
"We stayed two nights on a weekend to celebrate with family and our college graduate. We had 7 stay comfortably using the sunroom bed. The house was amazing and had everything we needed throughout the weekend. The backyard is very nice. We really loved everything about the house. The hosts were excellent, very helpful and extremely easy to communicate with. The neighborhood is very quiet and the location gives easy access to Madison. An amazing weekend! We would highly recommend!"
The price is AED 826
AED 1,058 total
includes taxes & fees
5 Jan - 6 January 2025
A Pleasant Retreat- No Cleaning Fee & New Discounts
‘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, (45)
"You could not imagine a more perfect location to stay. The privacy, views of the lake and the well appointed home were all provided the perfect makings for a glorious vacation. "
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
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!

9.8 out of 10, Exceptional, (31)
"Jake’s place was perfect for our stay, as it was a relaxing, clean and a nice home. The two floor layout worked especially well for our infant daughter so she had a quiet place to sleep, while we could cook and hang out in the living room. The only suggestion to the host is to install curtains along the picturesque sliding doors for a bit of extra privacy at nighttime."
The price is AED 937
AED 1,905 total
includes taxes & fees
1 Jan - 2 January 2025
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.