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
Fromد.إ.‏1,036 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
Fromد.إ.‏241 per night
6.6 (483 Reviews)
83 Bedrooms 20 Guests
DoubleTree by Hilton Madison East
Fromد.إ.‏449 per night
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9.4 (1007 Reviews)
1 Bedroom 2 Guests
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
10.0 (14 Reviews)
3 Bedrooms 12 Guests
Par-fect Escape on Lake Windsor Golf Course
New
1 Bedroom 10 Guests
Hampton Inn Madison East Towne Mall Area
9.4 (1001 Reviews)
1 Bedroom 2 Guests
Private Pool - Hot Tub - Sauna - Game Room - Pets
10.0 (11 Reviews)
5 Bedrooms 20 Guests
206 - King Suite
Fromد.إ.‏862 per night
9.7 (3 Reviews)
1 Bedroom 3 Guests
4 Bed, 3 Bath w/Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course
10.0 (4 Reviews)
4 Bedrooms 10 Guests
204 - Double Queen
Fromد.إ.‏829 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
Hampton Inn Madison East Towne Mall Area
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9.2 (100 Reviews)
115 Bedrooms 16 Guests
1 Bedroom Apartment at Canterbury Court
Fromد.إ.‏583 per night
10.0 (1 Review)
1 Bedroom 2 Guests
Hilton Garden Inn Madison Sun Prairie
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9.2 (59 Reviews)
117 Bedrooms 32 Guests
1 Bedroom Apartment at Canterbury Court
Fromد.إ.‏489 per night
10.0 (1 Review)
1 Bedroom 2 Guests
203 - Double Queen
Fromد.إ.‏725 per night
9.0 (5 Reviews)
1 Bedroom 5 Guests
Comfort Inn & Suites Madison North
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8.9 (153 Reviews)
14 Bedrooms 41 Guests
Capital City- 6 Miles from Madison with fireplace
9.8 (42 Reviews)
4 Bedrooms 12 Guests
Fairfield Inn and Suites by Marriott Madison East
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8.7 (71 Reviews)
130 Bedrooms 39 Guests
Entire 3 Bedroom with Fireplace - sleeps 12
9.8 (16 Reviews)
3 Bedrooms 10 Guests
201 -Single Queen
Fromد.إ.‏417 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
Doubletree By Hilton Madison East
Fromد.إ.‏419 per night
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8.5 (289 Reviews)
225 Bedrooms 40 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
9.0 (37 Reviews)
1 Bedroom 2 Guests
MainStay Suites Madison Airport
Fromد.إ.‏365 per night
8.5 (171 Reviews)
66 Bedrooms 32 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
8.8 (21 Reviews)
2 Bedrooms 6 Guests
Holiday Inn Express & Suites Madison by IHG
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8.5 (132 Reviews)
139 Bedrooms 42 Guests
Home away from home!
Fromد.إ.‏582 per night
8.8 (16 Reviews)
1 Bedroom 3 Guests
202 - Single Queen
Fromد.إ.‏681 per night
8.5 (2 Reviews)
1 Bedroom 2 Guests
King Suite. Free Breakfast. Pool. Near UW-Madison!
8.6 (7 Reviews)
1 Bedroom 2 Guests
Holiday Inn Express Deforest Madison Area by IHG
8.4 (84 Reviews)
106 Bedrooms 30 Guests
Free Breakfast. Pool + Hot Tub. Near UW-Madison!
8.4 (16 Reviews)
1 Bedroom 4 Guests
Courtyard by Marriott Madison East
Fromد.إ.‏615 per night
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8.3 (79 Reviews)
127 Bedrooms 47 Guests
Staybridge Suites Madison - East by IHG
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8.2 (90 Reviews)
121 Bedrooms 36 Guests
Par-fect Escape on Lake Windsor Golf Course
New
3 Bedrooms 8 Guests
Fantastic 3-bedroom house with AC in enchanting Windsor
New
3 Bedrooms 5 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
New
2 Bedrooms 4 Guests
Charming 3-Bedroom House in Quiet Madison Suburb
New
3 Bedrooms 6 Guests
Beautiful, Newly-Renovated 1-Bedroom Apartment in Madison
New
1 Bedroom 3 Guests
205 - Queen Suite
Fromد.إ.‏758 per night
8.0 (3 Reviews)
1 Bedroom 2 Guests
Holiday Inn Express & Suites Madison by IHG
9.4 (698 Reviews)
1 Bedroom 2 Guests
Free Covered Parking & Laundry. Dishwasher.
New
1 Bedroom 2 Guests
PrimeStay Extended Suites by IHG
Fromد.إ.‏403 per night
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7.9 (39 Reviews)
69 Bedrooms 32 Guests
Hilton Garden Inn Madison Sun Prairie
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9.4 (361 Reviews)
1 Bedroom 2 Guests
Upscale Modern appt near the Airport and Warner Park!
New
1 Bedroom 3 Guests
La Quinta by Wyndham Madison American Center
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7.7 (789 Reviews)
111 Bedrooms 21 Guests
The Mill Hotel
Fromد.إ.‏357 per night
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9.4 (69 Reviews)
1 Bedroom 2 Guests
Apartment Suite Penthouse located at hotel on Madison's east side!
7.4 (3 Reviews)
1 Bedroom 6 Guests
Best Western East Towne Suites
Fromد.إ.‏435 per night
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7.7 (274 Reviews)
194 Bedrooms 28 Guests
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
6.8 (5 Reviews)
2 Bedrooms 4 Guests
Cambria Hotel Madison East
Fromد.إ.‏424 per night
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7.6 (155 Reviews)
119 Bedrooms 38 Guests
Holiday Inn Madison at The American Center by IHG
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7.4 (211 Reviews)
271 Bedrooms 34 Guests
Super 8 by Wyndham Sun Prairie/Madison E
7.3 (128 Reviews)
53 Bedrooms 23 Guests
ECHO Suites Extended Stay by Wyndham Madison
7.2 (55 Reviews)
124 Bedrooms 24 Guests
Tru By Hilton Madison East
Fromد.إ.‏580 per night
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7.0 (1 Review)
64 Bedrooms 10 Guests
Grandstay Hotel & Suites
Fromد.إ.‏364 per night
6.9 (45 Reviews)
32 Bedrooms 22 Guests
Valued Stay Aloha
Fromد.إ.‏318 per night
6.7 (48 Reviews)
2 Bedrooms 6 Guests
AmericInn by Wyndham Madison WI
Fromد.إ.‏347 per night
6.4 (457 Reviews)
82 Bedrooms 9 Guests
Rodeway Inn & Suites Madison East
Fromد.إ.‏299 per night
6.1 (133 Reviews)
84 Bedrooms 15 Guests
Super 8 by Wyndham Windsor/Madison North
5.9 (48 Reviews)
29 Bedrooms 10 Guests
Valued Stay Sun Prairie
Fromد.إ.‏488 per night
5.0 (9 Reviews)
2 Bedrooms 3 Guests
Motel 6-Madison, WI - East
Fromد.إ.‏257 per night
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4.6 (565 Reviews)
91 Bedrooms 31 Guests
Red Roof Inn Madison, WI
Fromد.إ.‏280 per night
3.7 (125 Reviews)
6 Bedrooms 14 Guests
Home2 Suites By Hilton Madison East
Fromد.إ.‏600 per night
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New
149 Bedrooms 38 Guests
Fairfield Inn & Suites by Marriott Madison East
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9.2 (1002 Reviews)
1 Bedroom 2 Guests

About Casai's Private Villas and Holiday Rentals in Windsor

Discover more than 128 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 456.09 ft², with nightly prices averaging د.إ.‏731.

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.ae holiday rentals are available in Windsor?

As of 2026, Casai boasts over 128 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.