Windsor Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windsor, Wisconsin, USA

Luxury Prairie Retreat 5 Min from Madison!
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10.0 (1 Review)
3 Bedrooms 10 Guests
The Speckled Hen Inn B&B
FromZA R4,551 per night
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9.8 (9 Reviews)
1 Bedroom 2 Guests
A TOUCH OF COUNTRY LIVING Minutes from Madison
10.0 (181 Reviews)
2 Bedrooms 4 Guests
Econo Lodge Madison East
FromZA R979 per night
7.1 (422 Reviews)
83 Bedrooms 20 Guests
DoubleTree by Hilton Madison East
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9.4 (1005 Reviews)
1 Bedroom 2 Guests
Bonnie's Private City Cabin-Madison's Only Log Cabin Rental
10.0 (71 Reviews)
1 Bedroom 2 Guests
Par-fect Escape on Lake Windsor Golf Course
New
1 Bedroom 10 Guests
Hampton Inn Madison East Towne Mall Area
9.4 (1002 Reviews)
1 Bedroom 2 Guests
Luxury 'Prairie Retreat': 5 Min from Madison!
10.0 (15 Reviews)
3 Bedrooms 10 Guests
206 - King Suite
FromZA R3,788 per night
9.7 (3 Reviews)
1 Bedroom 3 Guests
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
10.0 (13 Reviews)
2 Bedrooms 12 Guests
204 - Double Queen
FromZA R3,642 per night
9.5 (2 Reviews)
1 Bedroom 4 Guests
Private Pool - Hot Tub - Sauna - Game Room - Pets
10.0 (10 Reviews)
5 Bedrooms 20 Guests
Hilton Garden Inn Madison Sun Prairie
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9.2 (59 Reviews)
117 Bedrooms 32 Guests
Free Breakfast Pool & Hot Tub. Near UW-Madison
10.0 (1 Review)
2 Bedrooms 4 Guests
Hampton Inn Madison East Towne Mall Area
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9.1 (93 Reviews)
115 Bedrooms 16 Guests
1 Bedroom - 1218 Canterbury Ct
FromZA R2,303 per night
10.0 (1 Review)
1 Bedroom 2 Guests
203 - Double Queen
FromZA R3,642 per night
9.0 (5 Reviews)
1 Bedroom 5 Guests
Courtyard by Marriott Madison East
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8.9 (75 Reviews)
112 Bedrooms 29 Guests
Capital PrimeTime - 6 Miles from Madison w/fireplace
9.8 (36 Reviews)
4 Bedrooms 12 Guests
Fairfield Inn and Suites by Marriott Madison East
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8.8 (76 Reviews)
88 Bedrooms 41 Guests
Entire 3 Bedroom with Fireplace - sleeps 12
9.8 (16 Reviews)
3 Bedrooms 10 Guests
201 -Single Queen
FromZA R2,615 per night
8.7 (3 Reviews)
1 Bedroom 2 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
8.8 (36 Reviews)
1 Bedroom 2 Guests
Comfort Inn & Suites Madison North
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8.6 (182 Reviews)
13 Bedrooms 36 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
8.8 (21 Reviews)
2 Bedrooms 6 Guests
Doubletree By Hilton Madison East
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8.5 (291 Reviews)
225 Bedrooms 40 Guests
Home away from home!
FromZA R2,193 per night
8.8 (15 Reviews)
1 Bedroom 3 Guests
MainStay Suites Madison Airport
FromZA R1,603 per night
8.5 (171 Reviews)
66 Bedrooms 32 Guests
King Suite. Free Breakfast. Pool. Near UW-Madison!
8.6 (7 Reviews)
1 Bedroom 2 Guests
Holiday Inn Express & Suites Madison by IHG
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8.5 (132 Reviews)
139 Bedrooms 42 Guests
Free Breakfast. Pool + Hot Tub. Near UW-Madison!
8.4 (16 Reviews)
1 Bedroom 4 Guests
202 - Single Queen
FromZA R2,991 per night
8.5 (2 Reviews)
1 Bedroom 2 Guests
Par-fect Escape on Lake Windsor Golf Course
New
3 Bedrooms 8 Guests
Holiday Inn Express Deforest by IHG
8.4 (92 Reviews)
108 Bedrooms 36 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
New
2 Bedrooms 4 Guests
Staybridge Suites Madison - East by IHG
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8.0 (106 Reviews)
121 Bedrooms 36 Guests
1 Bedroom - 1220 Canterbury Ct
FromZA R2,092 per night
New
1 Bedroom 2 Guests
Charming 3-Bedroom House in Quiet Madison Suburb
New
3 Bedrooms 6 Guests
HOT TUB - 20min to Capitol - Deck - Yard - Firepit
10.0 (2 Reviews)
4 Bedrooms 14 Guests
Apartment Suite Penthouse located at hotel on Madison's east side!
7.4 (3 Reviews)
1 Bedroom 6 Guests
205 - Queen Suite
FromZA R3,330 per night
8.0 (3 Reviews)
1 Bedroom 2 Guests
Holiday Inn Express & Suites Madison by IHG
9.4 (690 Reviews)
1 Bedroom 2 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
6.8 (5 Reviews)
2 Bedrooms 4 Guests
PrimeStay Extended Suites by IHG
FromZA R1,770 per night
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7.8 (32 Reviews)
69 Bedrooms 32 Guests
Hilton Garden Inn Madison Sun Prairie
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9.4 (347 Reviews)
1 Bedroom 2 Guests
La Quinta by Wyndham Madison American Center
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7.7 (779 Reviews)
111 Bedrooms 21 Guests
The Mill Hotel
FromZA R1,569 per night
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9.4 (63 Reviews)
1 Bedroom 2 Guests
Holiday Inn Madison at The American Center by IHG
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7.7 (206 Reviews)
271 Bedrooms 34 Guests
Fairfield Inn & Suites by Marriott Madison East
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9.2 (1007 Reviews)
1 Bedroom 2 Guests
Cambria Hotel Madison East
FromZA R3,027 per night
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7.7 (156 Reviews)
119 Bedrooms 38 Guests
ECHO Suites Extended Stay by Wyndham Madison
7.5 (30 Reviews)
124 Bedrooms 24 Guests
Best Western East Towne Suites
FromZA R2,324 per night
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7.4 (275 Reviews)
194 Bedrooms 28 Guests
Super 8 by Wyndham Sun Prairie/Madison E
7.4 (128 Reviews)
53 Bedrooms 23 Guests
Grandstay Hotel & Suites
FromZA R1,630 per night
6.9 (45 Reviews)
32 Bedrooms 22 Guests
AmericInn by Wyndham Madison WI
FromZA R1,243 per night
6.5 (378 Reviews)
82 Bedrooms 9 Guests
Valued Stay Aloha
FromZA R1,372 per night
6.1 (32 Reviews)
2 Bedrooms 6 Guests
Super 8 by Wyndham Windsor/Madison North
5.5 (47 Reviews)
35 Bedrooms 17 Guests
Rodeway Inn & Suites Madison East
5.2 (150 Reviews)
84 Bedrooms 15 Guests
Motel 6-Madison, WI - East
FromZA R1,130 per night
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5.0 (534 Reviews)
91 Bedrooms 31 Guests
Valued Stay Sun Prairie
FromZA R2,147 per night
5.0 (9 Reviews)
2 Bedrooms 3 Guests
Red Roof Inn Madison, WI
FromZA R1,278 per night
3.9 (125 Reviews)
6 Bedrooms 14 Guests
Tru By Hilton Madison East
FromZA R2,550 per night
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New
64 Bedrooms 10 Guests
Home2 Suites By Hilton Madison East
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New
148 Bedrooms 38 Guests
Courtyard by Marriott Madison East
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9.0 (647 Reviews)
1 Bedroom 2 Guests
Cambria Hotel Madison East
FromZA R1,798 per night
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8.8 (1004 Reviews)
1 Bedroom 2 Guests
Comfort Inn & Suites Madison North
8.8 (925 Reviews)
1 Bedroom 2 Guests

About Windsor Vacation Rentals

With more than 125 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Windsor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 451.4 ft² on average, with prices averaging ZA R2,946 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Windsor, WI


Frequently Asked Questions About Windsor?

What are the top vacation rentals in Windsor?

How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 125 in the Windsor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor.