Windsor Holiday Rentals

Compare Villas, Resorts, & Rentals in Windsor, Wisconsin, USA

A TOUCH OF COUNTRY LIVING Minutes from Madison
10.0 (181 Reviews)
2 Bedrooms 4 Guests
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 R4,666 per night
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9.8 (9 Reviews)
1 Bedroom 2 Guests
Bonnie's Private City Cabin-Madison's Only Log Cabin Rental
10.0 (71 Reviews)
1 Bedroom 2 Guests
Econo Lodge Madison East
FromZA R1,004 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
Luxury 'Prairie Retreat': 5 Min from Madison!
10.0 (15 Reviews)
3 Bedrooms 10 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
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
10.0 (13 Reviews)
3 Bedrooms 12 Guests
206 - King Suite
FromZA R3,883 per night
9.7 (3 Reviews)
1 Bedroom 3 Guests
Private Pool - Hot Tub - Sauna - Game Room - Pets
10.0 (10 Reviews)
5 Bedrooms 20 Guests
204 - Double Queen
FromZA R3,734 per night
9.5 (2 Reviews)
1 Bedroom 4 Guests
Free Breakfast Pool & Hot Tub. Near UW-Madison
10.0 (1 Review)
2 Bedrooms 4 Guests
Hilton Garden Inn Madison Sun Prairie
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9.2 (59 Reviews)
117 Bedrooms 32 Guests
1 Bedroom - 1218 Canterbury Ct
FromZA R2,441 per night
10.0 (1 Review)
1 Bedroom 2 Guests
Hampton Inn Madison East Towne Mall Area
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9.1 (93 Reviews)
115 Bedrooms 16 Guests
203 - Double Queen
FromZA R3,267 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 City- 6 Miles from Madison with fireplace
9.8 (37 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 R2,317 per night
8.7 (3 Reviews)
1 Bedroom 2 Guests
20min to Capitol - Garage - Yard - KING Bed - Pets
9.8 (7 Reviews)
4 Bedrooms 16 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 (36 Reviews)
1 Bedroom 2 Guests
Doubletree By Hilton Madison East
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8.5 (291 Reviews)
225 Bedrooms 40 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
8.8 (21 Reviews)
2 Bedrooms 6 Guests
MainStay Suites Madison Airport
FromZA R1,644 per night
8.5 (171 Reviews)
66 Bedrooms 32 Guests
Home away from home!
FromZA R2,248 per night
8.8 (15 Reviews)
1 Bedroom 3 Guests
Holiday Inn Express & Suites Madison by IHG
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8.5 (132 Reviews)
139 Bedrooms 42 Guests
King Suite. Free Breakfast. Pool. Near UW-Madison!
8.6 (7 Reviews)
1 Bedroom 2 Guests
202 - Single Queen
FromZA R3,066 per night
8.5 (2 Reviews)
1 Bedroom 2 Guests
Free Breakfast. Pool + Hot Tub. Near UW-Madison!
8.4 (16 Reviews)
1 Bedroom 4 Guests
Holiday Inn Express Deforest by IHG
8.4 (92 Reviews)
108 Bedrooms 36 Guests
Staybridge Suites Madison - East by IHG
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8.0 (106 Reviews)
121 Bedrooms 36 Guests
Par-fect Escape on Lake Windsor Golf Course
New
3 Bedrooms 8 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
New
2 Bedrooms 4 Guests
1 Bedroom - 1220 Canterbury Ct
FromZA R2,144 per night
New
1 Bedroom 2 Guests
Charming 3-Bedroom House in Quiet Madison Suburb
New
3 Bedrooms 6 Guests
Apartment Suite Penthouse located at hotel on Madison's east side!
7.4 (3 Reviews)
1 Bedroom 6 Guests
205 - Queen Suite
FromZA R3,414 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 R1,814 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 R1,609 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 R1,908 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 R1,962 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 R1,671 per night
6.9 (45 Reviews)
32 Bedrooms 22 Guests
AmericInn by Wyndham Madison WI
FromZA R1,506 per night
6.5 (378 Reviews)
82 Bedrooms 9 Guests
Valued Stay Aloha
FromZA R1,434 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 R1,158 per night
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5.0 (534 Reviews)
91 Bedrooms 31 Guests
Valued Stay Sun Prairie
FromZA R2,201 per night
5.0 (9 Reviews)
2 Bedrooms 3 Guests
Red Roof Inn Madison, WI
FromZA R1,260 per night
3.7 (125 Reviews)
6 Bedrooms 14 Guests
Home2 Suites By Hilton Madison East
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New
148 Bedrooms 38 Guests
Tru By Hilton Madison East
FromZA R2,614 per night
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New
64 Bedrooms 10 Guests
Courtyard by Marriott Madison East
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9.0 (647 Reviews)
1 Bedroom 2 Guests
Cambria Hotel Madison East
FromZA R1,844 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 Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 125 vacation rentals available in Windsor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windsor.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windsor. On average, places to stay near Windsor offer 451.4 ft², with nightly prices averaging ZA R3,060.

With Casai, finding and comparing holiday rentals in Windsor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply 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 holiday rentals in Windsor?

How many Casai.co.za holiday rentals are available in Windsor?

As of 2026, Casai boasts over 125 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.