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Compare 73 Vacation Homes in Windsor with updated reviews, rates, and availability.

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"We needed a place for a group of family members to stay to prepare food and decorations for a 60th birthday party at a nearby location. We had everything we needed and our hosts provided other prep items that aren’t commonly found in a rental home. The location was ideal (near a grocery store for forgotten items) and so comfortable!"
A Pleasant Retreat- No Cleaning Fee & New Discounts

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

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

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

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AED 937
AED 1,905 total
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Waterfront w/ HOT TUB + King Suite + Game Room

9.6 out of 10, Exceptional, (25)
"Fantastic place, very clean and great location. We will book this place again. "
Waterfront w/ HOT TUB + King Suite + Game Room

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (129)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (7)
"Very clean, great communication. Great location for Madison, Shops at Paoli, New Glarus, Epic. Close to downtown Verona. Having separate parking was nice. Not having a thermostat (or one I could find) was odd. Great place overall."
Paoli Den - Newly Remodeled!

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!

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

10.0 out of 10, Exceptional, (83)
"My college friends and I had the most lovely time at this cozy cabin! Everything was as mentioned in the description, the lake and views were stunning. We hiked nearby and happened upon the outdoor market in Baraboo. Saturday night dinner at Fish Tales just down the road was excellent. Highly recommended, will be back next year!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (156)
"Ben and Sara were great hosts - very communicative! Perfect little house and we loved watching sports on the big tv downstairs!"
Amazing townhouse, amazing attractions, amazing city!

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

10.0 out of 10, Exceptional, (24)
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Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

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!

Waters Edge Private Cottage

8.0 out of 10, Very Good, (6)
"For people 'of a certain age' like us, there was NO TV for 3 days because we do Not has streaming services.....so there was absolutely NO television option. It was in the fine print/description, we just didn't realize that meant NO TV options at all, so be aware of that. That being said, the location and view was ideal and beautiful!"
Waters Edge Private Cottage

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

10.0 out of 10, Exceptional, (5)
"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

10.0 out of 10, Exceptional, (12)
"This is one of the best rental homes I've ever stayed in! The owners were super accommodating and everything was labeled clearly. We stayed with a toddler and there were ample toddler toys and games, kid friendly cups and plates, and they even installed a baby gate at the top of the stairs. The neighborhood was great and quiet, with easy parking. Overall awesome, and we would love to stay here again!"
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake

9.6 out of 10, Exceptional, (10)
"We visited in late October, early November, so we didn't do much on the lake, but there is a cute park with a playground nearby! The house was clean and accommodating, even had a high chair for our use which was helpful with a 15 month old. We made all our meals in the house and found cooking utensils/dishes to be a little sporadic, but that was our only complaint. Stephen was a wonderful host who communicated clearly and quickly whenever we had questions! The view of the lake is gorgeous!"
Lakefront 4BR ‘Up North’ Outdoor Getaway - Best Sunset View on The Lake

Family-Friendly Lake Waubesa Home: Boat + Swim!

9.8 out of 10, Exceptional, (8)
"We were there at the start of fall and the gas fireplaces were awesome both for the ambiance and warmth on cooler days. The view from the sunroom was wonderful. We spent a lot of time enjoying the view from there. It had a nice mix of modern amenities (updated kitchen and baths) and rustic charm. The neighborhood was very cute. We walked our dog quite a bit and enjoyed views of the lake side homes and the lake from all around the house. Plus there are two parks both within walking distance...
Family-Friendly Lake Waubesa Home: Boat + Swim!

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

Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!

8.0 out of 10, Very Good, (7)
"Lovely property and spacious home with lots of good hangout areas. Fully stocked with anything u could need and nice decorations throughout"
Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!

Remodeled 3 bedroom home in Monona. Close to Downtown!

10.0 out of 10, Exceptional, (24)
"This is a really nice, very clean and comfortable home, in a quiet neighborhood that felt completely safe. Luke (homeowner) was quick to respond to all of my questions before and during, and even responded with a phone call when I had a question that required a quick answer. Plenty of comfy spaces both inside and out and a big enough home layout to allow some to go to bed while others stayed up to talk or watch the big-screen television. Just one bathroom, but plenty of hot water (even with 4...
Remodeled 3 bedroom home in Monona. Close 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.
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Other property types in Windsor

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

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is AED 937
AED 1,905 total
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!

9.8 out of 10, Exceptional, (229)
"We thoroughly enjoyed our stay. The bird watching and wildlife was spectacular. The host was very attentive. Highly recommend."
Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
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.