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Windsor vacation rentals

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Best Windsor vacation rentals

Most recommended vacation rentals in Windsor

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Econo Lodge Madison East - Madison - Bedroom
Econo Lodge Madison East
Madison, WI
6.9Okay(626)
Parking
Free Wi-Fi
Pet friendly
$75+
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Willy St Prime Location 2nd Flr Secure Entrance - Madison - Outdoors view
Willy St Prime Location 2nd Flr Secure Entrance
Madison, WI
Free Wi-Fi
$108+
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King Suite. Free Breakfast. Pool. Near Uw-Madison! - Madison - Patio
King Suite. Free Breakfast. Pool. Near Uw-Madison!
Madison, WI
Free Wi-Fi
Pool
Spa
$307+
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Free Parking-walk to hospital&campus-fast wifi! - Madison - Building
Free Parking-walk to hospital&campus-fast wifi!
Madison, WI
$113+
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Lakefront Condo Excellent Location! With Parking/Kayak And Boat Rentals! - Madison - Balcony
Lakefront Condo Excellent Location! With Parking/Kayak And Boat Rentals!
Madison, WI
Free Wi-Fi
Pet friendly
$93+
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Liberty Valley Short Term Rental - 29 - Madison - Building
Liberty Valley Short Term Rental - 29
Madison, WI
Parking
Free Wi-Fi
$104+
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Remodeled 3 bedroom home in Monona. Close to Downtown! - Madison - Living room
Remodeled 3 bedroom home in Monona. Close to Downtown!
Madison, WI
Free Wi-Fi
Pet friendly
$668+
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Free Breakfast. Pool. Downtown Location. Great for Business Travelers! - Middleton - Patio
Free Breakfast. Pool. Downtown Location. Great for Business Travelers!
Middleton, WI
Free Wi-Fi
Pool
Spa
$197+
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Free Breakfast. Pool and Hot Tub. Downtown Location. Close to the University of Wisconsin-Madison! - Middleton - Restaurant
Free Breakfast. Pool and Hot Tub. Downtown Location. Close to the University of Wisconsin-Madison!
Middleton, WI
Free Wi-Fi
Pool
Spa
$329+
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Beautiful Lake Monona Home-Minutes to Downtown Madison - Madison - Living room
Beautiful Lake Monona Home-Minutes to Downtown Madison
Madison, WI
Free Wi-Fi
Pool
$3,357+
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Liberty Valley Short Term Rental - 27 - Madison
Liberty Valley Short Term Rental - 27
Madison, WI
9.0Wonderful(1)
Parking
Free Wi-Fi
$104+
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Free Breakfast. Pool & Hot Tub. Near Uw-Madison! - Madison - Patio
Free Breakfast. Pool & Hot Tub. Near Uw-Madison!
Madison, WI
Free Wi-Fi
Pool
Spa
$267+
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Doty Walk to Everything -Hotel Quality- Downtown - Madison - Bedroom
Doty Walk to Everything -Hotel Quality- Downtown
Downtown
Free Wi-Fi
$1,241+
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Cannery Square Short Term Rentals -102 - Sun Prairie - Bedroom
Cannery Square Short Term Rentals -102
Sun Prairie, WI
Parking
Free Wi-Fi
$325+
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Free Breakfast. Pool & Hot Tub. Near Uw-Madison! - Madison
Free Breakfast. Pool & Hot Tub. Near Uw-Madison!
Madison, WI
Pool
Spa
$152+
Check availability
Jacuzzi 1BR loft w/ den/office-open concept - Madison
Jacuzzi 1BR loft w/ den/office-open concept
Downtown
$111+
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Good to know

Low season

May

High season

May
Cheapest month to stay with an average 0% drop in price.
Most expensive month to stay with an average 0% rise in price.

KAYAK's top tips for finding Windsor vacation rental deals

  • The best vacation rental properties in Windsor are Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard (10.0, 32 reviews), Remodeled 3 bedroom home in Monona. Close to Downtown! (10.0, 21), and Happys Haven Cabin with Gas Grill and Fire Pit! (10.0, 39), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windsor for 2 days.

FAQs when booking a vacation home in Windsor

  • What types of vacation rentals are available in Windsor?

    in Windsor you’ll find that most vacation rentals are houses.

  • How can I find vacation rentals near me in Windsor?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windsor?

Our map will help you find the perfect place to stay in Windsor by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windsor

Windsor vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Windsor. Find cheap vacation homes to rent in Windsor. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Windsor that suits you best.

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