Title: Windsor Vacation Rentals from $150: Search Short-Term Rentals | Expedia.com

[Windsor Travel Guide](https://expedia.com/Windsor.dx180667)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d180667.Travel-Guide-Hotels)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d180667.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d180667.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d180667.Destination-Travel-Guides)

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We are not like the others - we include taxes and fees

## Check prices for these dates

In two weeks

[Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=180667&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=180667&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=180667&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=180667&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor vacation rentals

![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/a2858593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/eed91014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/39556d41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/86000000/85540000/85537300/85537244/5ab3b59a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Middleton

[](https://www.expedia.com/Madison-Hotels-King-Suite-Free-Breakfast-Pool-And-Hot-Tub.h85537244.Hotel-Information)

8.0/10

Very Good

(5 reviews)

"Great place for a stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andy D.

$120 nightly

$137 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-King-Suite-Free-Breakfast-Pool-And-Hot-Tub.h85537244.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74100000/74093800/74093714/aba7d103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74100000/74093800/74093714/2f85f131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74100000/74093800/74093714/58272a06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74100000/74093800/74093714/704fdccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Unit-106-By-Patriot-Properties.h74093714.Hotel-Information)

9.4/10

Exceptional

(28 reviews)

"Great place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Armando

$286 nightly

$322 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Unit-106-By-Patriot-Properties.h74093714.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/83622a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathtub, hair dryer, towels](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/91aed0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/b9f70f6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78120000/78111100/78111089/d3d01fda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Short-Term-Rentals-102-By-Patriot.h78111089.Hotel-Information)

8.0/10

Very Good

(12 reviews)

"Was cute neighborhood and everything was very clean and close by"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Bri

$246 nightly

$277 total

Mar 20 - Mar 21

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Short-Term-Rentals-102-By-Patriot.h78111089.Hotel-Information)

![TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/3cd5e81d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, foosball, offices](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/b000fe2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/f194f824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111240000/111234000/111233952/138b24d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sun Prairie

[](https://www.expedia.com/Sun-Prairie-Hotels-AMazing-Place-Summary.h111233952.Hotel-Information)

10/10

Exceptional

(18 reviews)

"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

George P.

$585 nightly

$696 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Sun-Prairie-Hotels-AMazing-Place-Summary.h111233952.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/ec91cc9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/0f817c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/cd9099b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88420000/88410700/88410689/717052e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-2-Bedroom-Main-Street-Sun-Prairie-WI.h88410689.Hotel-Information)

9.6/10

Exceptional

(39 reviews)

"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sha'Vonne G.

$361 nightly

$406 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-2-Bedroom-Main-Street-Sun-Prairie-WI.h88410689.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/7369ac14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/3efd103e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/12bdd8b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74640000/74637500/74637492/06426659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Verona

[](https://www.expedia.com/Verona-Hotels-Enjoy-Nature-With-Full-Comfort.h74637492.Hotel-Information)

9.2/10

Wonderful

(39 reviews)

"Clean very friendly nice spot"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Oliver H.

$139 nightly

$147 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Verona-Hotels-Enjoy-Nature-With-Full-Comfort.h74637492.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/cf9e642a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/79d75eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/9e5dccce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115340000/115333200/115333182/98b4110c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Fitchburg

[](https://www.expedia.com/Madison-Hotels-King-Suite-Free-Breakfast-Pool-With-A-Slide-Close-To-Olbrich-Botanical-Gardens.h115333182.Hotel-Information)

$150 nightly

$169 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-King-Suite-Free-Breakfast-Pool-With-A-Slide-Close-To-Olbrich-Botanical-Gardens.h115333182.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1024h682x0y1-669a016c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1023h682x1y1-375fab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/f7402a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27131100/27131051/w1023h682x1y1-1324bcc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-A-Pleasant-Retreat-For-1.h27131051.Hotel-Information)

10/10

Exceptional

(271 reviews)

"Everything was pleasant, location was convenient "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly J.

$284 nightly

$319 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-A-Pleasant-Retreat-For-1.h27131051.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/de864266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/80aa63ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/3f652e1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91680000/91678600/91678589/98181479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Merrimac

[](https://www.expedia.com/Merrimac-Hotels-NEW-OWNER-SPECIAL-Mid-Century-Cabin-W-Lakeview.h91678589.Hotel-Information)

9.8/10

Exceptional

(27 reviews)

"Beautiful property with a perfect view for fall color. Very comfortable and great space for both couples and family. We enjoyed a very relaxing stay. Host was very prompt with responses and easy to work with."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jenel S.

$415 nightly

$447 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Merrimac-Hotels-NEW-OWNER-SPECIAL-Mid-Century-Cabin-W-Lakeview.h91678589.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/93000000/92560000/92556500/92556475/ee30cc24_edited_d167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92560000/92556500/92556475/9f69ba7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92560000/92556500/92556475/9e90f932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/93000000/92560000/92556500/92556475/1f2f92df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Merrimac

[](https://www.expedia.com/Merrimac-Hotels-Waters-Edge-Private-Cottage.h92556475.Hotel-Information)

7.8/10

Good

(12 reviews)

"Won $500 pull tab this weekend. Would stay again."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ryan R.

$452 nightly

$509 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Merrimac-Hotels-Waters-Edge-Private-Cottage.h92556475.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/48c40e67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/b273577f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/10ff1c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/84000000/83140000/83137300/83137225/ef80e055.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Fitchburg

[](https://www.expedia.com/Madison-Hotels-Pool-With-Slide-Great-For-Business-Travelers.h83137225.Hotel-Information)

$150 nightly

$169 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Pool-With-Slide-Great-For-Business-Travelers.h83137225.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/915f9e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/923928f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/94b7dd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111999300/111999285/540b4e15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Village of Cottage Grove

[](https://www.expedia.com/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.Hotel-Information)

10/10

Exceptional

(11 reviews)

"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anakin F.

$400 nightly

$454 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Cottage-Grove-Hotels-Charming-3-Bedroom-Duplex-Unit-With-WiFi-In-Cottage-Grove.h111999285.Hotel-Information)

![Reception](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/b591d86e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![One Bedroom Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/9ae34cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite | Living area](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/a67fadd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Two Bedroom Suite - Queen/Queen | Dining room](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/593ef7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Tenney-Lapham

[](https://www.expedia.com/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information)

9.4/10

Exceptional

(131 reviews)

"Check in was easy, the room was super clean and cute, great amenities, close to the Sylvee and other bars/restaurants and the lake. Would stay again!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Caitlin

$129 nightly

$150 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/e901e932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/199c30da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/621d9da3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/75000000/74130000/74124600/74124541/f8090f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Downtown Madison

[](https://www.expedia.com/Madison-Hotels-Doty-Walk-To-Everything-Hotel-Quality-Downtown.h74124541.Hotel-Information)

9.8/10

Exceptional

(38 reviews)

"Wonderful host, and a beautiful home within walking distance to many restaurants and museums. Parking nearby was easy to find. We were able to rest and relax, and make many meals there. Great kitchen amenities, and very comfortable beds. Truly a warm and inviting home. I would highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacquie T.

$250 nightly

$289 total

Mar 17 - Mar 18

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Doty-Walk-To-Everything-Hotel-Quality-Downtown.h74124541.Hotel-Information)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/122000000/121730000/121722700/121722664/884db675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121730000/121722700/121722664/8bceb4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121730000/121722700/121722664/f3ec1600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121730000/121722700/121722664/1c372886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-Cozy-Modern-4BD-25BA-Home-With-Private-Pool-In-Sun-Prairie.h121722664.Hotel-Information)

10/10

Exceptional

(4 reviews)

"I had an excellent stay with Kingdom Hospitality. The home was immaculate, and I enjoyed the updated kitchen. The hot tub was clean, and a great amenity for stress relief. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Trey B.

$594 nightly

$656 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Cozy-Modern-4BD-25BA-Home-With-Private-Pool-In-Sun-Prairie.h121722664.Hotel-Information)

![Smart TV, computer monitors](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/2f2d26f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/d446c4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/f9754302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120680000/120679100/120679093/2e310a0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Middleton

[](https://www.expedia.com/Middleton-Hotels-Chic-Apartment-In-Amazing-Middleton-With-Fitness-Equipment.h120679093.Hotel-Information)

10/10

Exceptional

(2 reviews)

"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jessi P.

$277 nightly

$306 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Middleton-Hotels-Chic-Apartment-In-Amazing-Middleton-With-Fitness-Equipment.h120679093.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/4270c7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/ec4455e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/10858971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89790000/89783700/89783692/2f8cdff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monona

[](https://www.expedia.com/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.Hotel-Information)

9.8/10

Exceptional

(47 reviews)

"It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Justine K.

$442 nightly

$501 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-NEW-OWNER-SPECIALMadison-Lakefront-Home.h89783692.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/e73435fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/0675f8d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Spa](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/a9ab4368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83300000/83295200/83295120/876ac21e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Madison

[](https://www.expedia.com/Madison-Hotels-Free-Breakfast-Pool-Hot-Tub-Near-UW-Madison.h83295120.Hotel-Information)

10/10

Exceptional

(1 review)

"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joy E.

$237 nightly

$275 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Free-Breakfast-Pool-Hot-Tub-Near-UW-Madison.h83295120.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/8a317c5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/c87e9887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/64676f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112250000/112243000/112243000/511923cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Sun Prairie

[](https://www.expedia.com/Citys-EDGE-Of-Madison-6-Miles-To-Downtown.h112243000.Hotel-Information)

10/10

Exceptional

(14 reviews)

"Beautiful spacious property, extremely clean and excellent host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jen F.

$508 nightly

$572 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Citys-EDGE-Of-Madison-6-Miles-To-Downtown.h112243000.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/844f3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/70f4dce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/46d11777.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/70000000/69720000/69715700/69715655/b2ecd236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Sun Prairie

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Short-Term-Rentals-104-By-Patriot.h69715655.Hotel-Information)

9.6/10

Exceptional

(47 reviews)

"Walkable restaurants. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mike H.

$309 nightly

$348 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Madison-Hotels-Cannery-Square-Short-Term-Rentals-104-By-Patriot.h69715655.Hotel-Information)

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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## Find vacation rentals that suit your style

Aparthotels

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Private vacation homes

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Apartments

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Condos

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Cottages

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America&regionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=COTTAGE)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Wisconsin%2C+United+States+of+America&regionId=180667&latLong=43.218327%2C-89.341507&adults=2&startDate=2026-06-12&d1=2026-06-12&endDate=2026-06-15&d2=2026-06-15&lodging=CHALET)

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## Top Windsor Hotel Reviews

![Hampton Inn & Suites Madison-West](https://images.trvl-media.com/lodging/3000000/2140000/2135000/2134982/w3838h2560x2y0-00a75c6b_y.jpg)

### Hampton Inn & Suites Madison-West

10/10 Excellent

"Staff friendly. "

[](https://expedia.com/Madison-Hotels-Hampton-Inn-Suites-Madison-West.h2134982.Hotel-Information)

![Baymont by Wyndham Madison West/Middleton WI West](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/8204d66c_y.jpg)

### Baymont by Wyndham Madison West/Middleton WI West

6/10 Okay

"room carpet had a good worn spot on it, clean enough, wasnt told about breafast hours or wifi password at check in- had to go back & ask for kids, no meat option @ breafast- very basic to get going. pool has huge hot tube. "

[](https://expedia.com/Madison-Hotels-Baymont-By-Wyndham-Madison-WestMiddleton-WI-West.h40004.Hotel-Information)

![Tru by Hilton Madison West, WI](https://images.trvl-media.com/lodging/23000000/22170000/22166300/22166216/1c86f9a1_y.jpg)

### Tru by Hilton Madison West, WI

8/10 Good

"I have stayed at this hotel a couple times. The workout room is very nice. The hotel is very clean."

[](https://expedia.com/Madison-Hotels-Tru-By-Hilton-Madison-West.h22166216.Hotel-Information)

![The Dylin](https://images.trvl-media.com/lodging/111000000/110850000/110849800/110849795/b591d86e_y.jpg)

### The Dylin

10/10 Excellent

"Well-decorated, coffee/kitchenette setup was great! "

[](https://expedia.com/Madison-Hotels-The-Dylin-By-Locale.h110849795.Hotel-Information)

![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/5fd64d1f_y.jpg)

### The Madison Concourse Hotel and Governor's Club

10/10 Excellent

"Beautiful and clean hotel with excellent location. Very good experience!"

[](https://expedia.com/Madison-Hotels-The-Madison-Concourse-Hotel-And-Governors-Club.h28447.Hotel-Information)

![Best Western East Towne Suites](https://images.trvl-media.com/lodging/1000000/10000/9100/9095/9bd8f3c8_y.jpg)

### Best Western East Towne Suites

2/10 Terrible

"Front staff was very rude. He was not helpful at all. There was garbage laying around everywhere. Guests were hanging out in the hallways. Building smelled of marijuana. Our room had chipped paint, holes, plaster all over the walls, especially in the bathroom. Very unprofessional. "

[](https://expedia.com/Madison-Hotels-Best-Western-East-Towne-Suites.h9095.Hotel-Information)

![Best Western Premier Park Hotel](https://images.trvl-media.com/lodging/8000000/7050000/7043100/7043069/4f17c333_y.jpg)

### Best Western Premier Park Hotel

10/10 Excellent

"Clean, quiet, great location. Valet brought car very quickly every time. Restaurant/Bar on premises…breakfast was really good (albeit a bit pricey), drinks in bar before heading out for the evening was a nice touch. "

[](https://expedia.com/Madison-Hotels-Best-Western-Premier-Park-Hotel.h7043069.Hotel-Information)

![DoubleTree by Hilton Madison East](https://images.trvl-media.com/lodging/1000000/10000/3200/3157/e4eb5914_y.jpg)

### DoubleTree by Hilton Madison East

10/10 Excellent

"Friendly staff, clean room"

[](https://expedia.com/Madison-Hotels-DoubleTree-By-Hilton-Madison-East.h3157.Hotel-Information)

![Embassy Suites By Hilton Madison Downtown](https://images.trvl-media.com/lodging/105000000/104100000/104094900/104094803/c01c100f_y.jpg)

### Embassy Suites By Hilton Madison Downtown

10/10 Excellent

"Best breakfast. "

[](https://expedia.com/Madison-Hotels-Embassy-Suites-By-Hilton-Madison-Downtown.h104094803.Hotel-Information)

## Find out more about Windsor

**Everything you need to know about Windsor vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Windsor vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Windsor rentals**

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Windsor ](https://expedia.com/Windsor-Private-Vacation-Homes.d180667-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Apartments in Windsor ](https://expedia.com/Windsor-Apartments.d180667-aaApartments.Travel-Guide-Accommodation)
- [Cottages in Windsor ](https://expedia.com/Windsor-Cottages.d180667-aaCottages.Travel-Guide-Accommodation)
- [Condo Rentals in Windsor ](https://expedia.com/Windsor-Condos.d180667-aaCondos.Travel-Guide-Accommodation)
- [Motels in Windsor ](https://expedia.com/Windsor-Motels.d180667-aaMotels.Travel-Guide-Accommodation)
- [Cabin Rentals in Windsor ](https://expedia.com/Windsor-Cabins.d180667-aaCabins.Travel-Guide-Accommodation)
- [B&B in Windsor ](https://expedia.com/Windsor-Bed-And-Breakfast.d180667-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Guest Houses in Windsor ](https://expedia.com/Windsor-Guest-Houses.d180667-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in Windsor ](https://expedia.com/Windsor-Apart-Hotels.d180667-aaApartHotels.Travel-Guide-Accommodation)
- [Hostels in Windsor ](https://expedia.com/Windsor-Hostels.d180667-aaHostels.Travel-Guide-Accommodation)
- [Farmstay in Windsor ](https://expedia.com/Windsor-Agritourism.d180667-aaAgritourism.Travel-Guide-Accommodation)

## Frequently asked questions

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