Windsor Holiday Rentals, Madison: Private House Rentals

A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Our top choices for Windsor hotels

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a table.

A gym with treadmills, elliptical machines, and free weights.

A living room with a red sofa, patterned chairs, a glass coffee table, and a fireplace.

A Days Inn hotel with a covered entrance, brick pillars, and a parking lot.

1. Days Inn by Wyndham Madison NE/Windsor

Windsor

TARA

Rp1.162.283

Rp1.226.208 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, desk, chair, and a large painting on the wall.

A bathroom with a granite countertop sink, a mirror, and a towel rack.

A lobby with a large welcome sign, leather armchairs, a leather sofa, a clock, and a TV on a stand.

A motel with a Super 8 sign and a Topp's Mideaway sign.

2. Super 8 by Wyndham Windsor/Madison North

Windsor

Oswaldo

Rp1.133.496

Rp1.275.273 total

includes taxes & fees

29 Oct - 30 Oct

A modern hotel room with a bed, a desk, a chair, and a sofa.

A modern room with a blue wall, a wooden desk, a yellow office chair, a blue sofa, and a floor lamp.

An indoor swimming pool with blue and white tiled walls, a clear pool, and lounge chairs along the sides.

A compact hotel bathroom with a sink, mirror, and a small refrigerator.

3. Holiday Inn Express Deforest (Madison Area) by IHG

De Forest

William

Rp1.567.914

Rp1.732.544 total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with a fountain, lounge chairs, and a sunshade.

A bar area with a marble countertop, bar stools, a refrigerator stocked with beverages, and a clock on the wall.

A hotel room with a bed, a blue sofa, two small tables, a lamp, and two framed pictures on the wall.

A hotel room with a blue sofa, a brown ottoman, a white bathtub, and a large mirror.

4. Comfort Inn & Suites Madison North

De Forest

Kimberly

Rp1.496.934

Rp1.654.112 total

includes taxes & fees

15 Nov - 16 Nov

A spacious lobby with a high ceiling, a reception desk, and a display of various items on the wall.

An indoor swimming pool with clear markings for non-diving and diving areas, surrounded by lounge chairs and tables.

A modern bar area with a counter, seating, and a TV mounted on the wall.

A spacious lobby with a bar area, seating arrangements, and a decorative partition.

5. DoubleTree by Hilton Madison East

Greater Sandburg

Humberto

Rp1.903.194

Rp2.198.189 total

includes taxes & fees

31 Oct - 1 Nov

A spacious lobby with a high ceiling, a large chandelier, and a reception desk.

A lobby with a fireplace, two armchairs, and two small tables.

An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outdoors.

A hotel room with a flat-screen TV mounted on the wall, a kitchenette with a microwave and refrigerator, a desk with a chair, and a green upholstered chair.

6. La Quinta Inn & Suites by Wyndham Madison American Center

Madison

Caroline

Rp1.441.159

Rp1.664.539 total

includes taxes & fees

1 Nov - 2 Nov

A multi-story hotel with a prominent 'CAMBRIA' sign, featuring a brick facade, large windows, and a covered entrance area.

A modern bar area with a long counter, bar stools, and a television mounted above the bar.

An outdoor patio with tables and chairs, large windows, and a view of the surrounding greenery.

A spacious lobby with a stone wall, large windows, and comfortable seating areas.

7. Cambria Hotel Madison East

Madison

Kathleen

Rp1.514.027

Rp1.748.701 total

includes taxes & fees

11 Nov - 12 Nov

A Holiday Inn hotel with a glass entrance canopy, brick facade, and green lighting.

An indoor swimming pool with a stone wall, a seating area with chairs, and a sign indicating no lifeguard on duty.

A hotel room with a bed, a TV, a desk, a chair, a sofa, and a lamp.

A hotel corridor with striped chairs, potted plants, and a framed picture on the wall.

8. Holiday Inn Madison at The American Center by IHG

Madison

Shua

Rp1.279.562

Rp1.477.894 total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with multiple lounge chairs and a sign indicating no lifeguard on duty.

A hotel lobby with multiple seating areas, a bar, and a fireplace.

A hotel room with a bed, a desk with a telephone, a television on a wooden stand, and a small plant.

A hotel room with a desk, computer, printer, and a large mirror.

9. Fairfield Inn & Suites by Marriott Madison East

Madison

Brian

Rp1.684.051

Rp1.945.079 total

includes taxes & fees

2 Nov - 3 Nov

A spacious lobby with a high ceiling, a reception desk, seating area, and a TV screen.

An outdoor patio area with wicker furniture, tables, and chairs.

A hotel room with a large bed, a desk, and a chair. There is a window with a view of the city.

A modern lobby with a white sofa, blue armchair, and green armchairs. There is a fireplace, a desk with two monitors, and a large abstract painting on the wall.

10. Hilton Garden Inn Madison Sun Prairie

Sun Prairie

Dawn

Rp2.431.619

Rp2.735.571 total

includes taxes & fees

1 Nov - 2 Nov

A modern restaurant with a bar area, large windows with a city view, and a unique ceiling light fixture.

A hotel room with a bed, a bedside table with a bottle of champagne, glasses, and a tray.

A dining area with a view of a large dome building through large windows.

11. The Madison Concourse Hotel and Governor's Club

Downtown Madison

Lori

Rp2.125.755

Rp2.455.368 total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a view of a cityscape, including a prominent dome building.

A gym with exercise equipment, a wall of dumbbells, and large windows.

A conference room with multiple tables and chairs, arranged in a grid pattern.

A spacious lobby with seating areas, a reception desk, and a glass door entrance.

12. DoubleTree by Hilton Madison Downtown

Downtown Madison

ZOE

Rp2.019.962

Rp2.333.055 total

includes taxes & fees

19 Nov - 20 Nov

A hotel room with two beds, a desk, a chair, a flat-screen TV, and a window with a view.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

A modern kitchen area with a coffee station, a chalkboard menu, and a buffet counter with food displays.

A conference room with tables and chairs, a carpeted floor, and framed artwork on the wall.

13. Holiday Inn Express & Suites Madison by IHG

Madison

christy

Rp1.817.192

Rp2.098.857 total

includes taxes & fees

1 Nov - 2 Nov

A hotel corridor with wooden flooring, a railing, and a wall displaying various photographs.

A waterfront hotel with outdoor seating and a view of the sunset over the water.

A hotel with a view of the water at sunset, featuring a prominent entrance and multiple balconies.

A spacious bedroom with a large bed, a sitting area with a chair, and a view of the sea through large windows.

14. The Edgewater

Downtown Madison

Javier

Rp3.092.678

Rp4.029.983 total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with clear glass walls, red chairs, and a table with chairs.

A hotel room with a large bed, a desk, a chair, and a wardrobe.

A gym with treadmills, elliptical machines, free weights, and exercise balls.

A modern dining area with multiple tables and booths, red and brown patterned chairs, and large windows providing natural light.

15. Hampton Inn Madison East Towne Mall Area

Greater Sandburg

Cami

Rp1.819.891

Rp2.101.973 total

includes taxes & fees

29 Oct - 30 Oct

An outdoor patio area with wicker furniture, a central fire pit, and a building with a brick facade in the background.

A hotel room with a large bed, a sitting area with a red sofa, a small table, and a bathtub.

A modern lobby with a sofa, ottoman, and seating area with tables.

A modern hotel lobby with a bar area, seating, and a large screen displaying a video.

16. Courtyard by Marriott Madison East

Madison

scott

Rp1.684.051

Rp1.945.078 total

includes taxes & fees

9 Nov - 10 Nov

A modern building with a sign reading 'Highland Corner Grill.'

A gym with exercise equipment, large windows, and a view of the outside.

A restaurant with a buffet, wooden ceiling, and large windows overlooking the street.

17. Best Western Plus InnTowner Madison

Regent

Nichole

Rp2.034.715

Rp2.350.096 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with two separate sections, one with clear water and the other with a whirlpool feature. There are lounge chairs and umbrellas around the pool area, and large windows providing views of the outside.

A sunlit patio area with cushioned seating, a table, and a large umbrella.

A hotel lobby with a reception desk, seating area, and a TV screen.

A spacious lobby with a high ceiling, a large chandelier, and a seating area with patterned chairs and a sofa.

18. Best Western East Towne Suites

Madison

Kerry

Rp1.529.140

Rp1.766.157 total

includes taxes & fees

2 Nov - 3 Nov

An indoor swimming pool with wooden beams, clear poolside chairs, and a lifeguard chair.

A gym with cardio machines, weight machines, and a mirrored wall.

A living room with a sofa, armchairs, a coffee table, and a rug. There are large windows and a brick wall.

A dining area with wooden tables and chairs, a kitchen in the background, and a clock on the wall.

19. Quality Inn & Suites Sun Prairie Madison East

Sun Prairie

Michael

Rp1.225.496

Rp1.378.682 total

includes taxes & fees

22 Nov - 23 Nov

An outdoor seating area with a fire feature, large windows, and a brick wall.

A modern indoor space with a staircase, seating areas, and a large window.

A modern bar area with high ceilings, large windows, and a central bar counter with stools.

A modern hotel room with a desk, a grey sofa, a large window with a city view, and a wardrobe.

20. SpringHill Suites by Marriott Madison

Madison

Michael

Rp2.680.808

Rp3.096.423 total

includes taxes & fees

8 Nov - 9 Nov

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Stay near popular Windsor attractions

Mousehouse Cheesehaus

9.0/10 (12 reviews)

Enjoy an outing to Mousehouse Cheesehaus during your stay in Windsor. Wander the area's lakeside or simply enjoy one of its top-notch restaurants.

See properties

Learn more about Windsor

Bike the scenic Lake Windsor Park trails before cooling off at the splash pad on hot summer days. Families gather at Token Creek County Park just outside Windsor for fishing, picnicking, and exploring the natural springs.

See all hotels in Windsor

Top Windsor Hotel Reviews

The Madison Concourse Hotel and Governor's Club

8/10 Good

"It’s downtown. Easy to walk to either lake."

Best Western Premier Park Hotel

10/10 Excellent

"Have stayed there before it’s always nice"

DoubleTree by Hilton Madison East

10/10 Excellent

"Great property and helpful staff."

AmericInn by Wyndham Madison West

10/10 Excellent

"Very clean hotel. The staff were very nice and helpful. The breakfast was awesome! Will start again when we have to go back down to UW Madison hospital."

Hampton Inn & Suites Madison-West

8/10 Good

"It was clean and spacious and good for the one night we stayed. You could hear through the walls and into the hallway quite easily, so I would not want to stay here for a long period or if I knew I would be in the hotel a lot."

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent

"It’s very clean and well served breakfast at our stay thanks and we will for sure come again."

Days Inn & Suites by Wyndham Madison

10/10 Excellent

"everything was perfect"

DoubleTree by Hilton Madison Downtown

10/10 Excellent

"The rooms are small but comfortable, and the bed and pillows are very comfortable! Location is great, front-desk staff are very friendly and helpful. The exercise gym is spacious and well-designed, looking onto a small patio. This is my second stay at this hotel and I would book it again when returning to downtown Madison."

More cheap stays in Windsor

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI

Rp791.468

Rp914.144 total

5 Nov - 6 Nov

includes taxes & fees

6.2/10 (1,052 reviews)

Baymont Inn & Suites by Wyndham Madison

2810 Coho Street Madison WI

Rp1.068.524

Rp1.234.145 total

22 Nov - 23 Nov

includes taxes & fees

Econo Lodge Madison East

4726 E Washington Ave Madison WI

Rp1.111.006

Rp1.283.369 total

25 Oct - 26 Oct

includes taxes & fees

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr Madison WI

Rp1.177.576

Rp1.360.101 total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,492 reviews)

Super 8 by Wyndham Madison South

1602 W Beltline Hwy Madison WI

Rp1.180.275

Rp1.363.217 total

8 Nov - 9 Nov

includes taxes & fees

7.2/10 Good! (1,007 reviews)

Comfort Suites Madison West - Middleton

1253 John Q Hammons Dr Madison WI

Rp1.239.436

Rp1.431.548 total

22 Nov - 23 Nov

includes taxes & fees

8.2/10 Very good! (641 reviews)

Frequently asked questions

What's the best place to stay in Windsor?

Days Inn by Wyndham Madison NE/Windsor is one of the top choices for your stay based on our traveller data. This hotel offers free breakfast and an indoor pool. Other good choices for your visit to the area are The Madison Concourse Hotel and Governor's Club and Best Western Plus InnTowner Madison. See all available top hotels, or vacation rentals in Windsor.

If I need to cancel my hotel reservation in Windsor, will I receive a refund?

Yes! Most hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Windsor.

What's the best family accommodation in Windsor?

Days Inn by Wyndham Madison NE/Windsor is a hotel with an indoor pool and free parking, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Mousehouse Cheesehaus. Find more child-friendly accommodations in Windsor.

What's the best dog-friendly place to stay in Windsor?

Super 8 by Wyndham Windsor/Madison North is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Windsor.

What are some hotels with pools in Windsor?

Days Inn by Wyndham Madison NE/Windsor: Features a sauna, an indoor pool and daily. The Madison Concourse Hotel and Governor's Club and Best Western Plus InnTowner Madison are a couple of other choices that offer an on-site pool. View all hotels with pools in Windsor.

What's it like to stay in Windsor?

Budget-minded travellers will find good deals in Windsor, and many visitors will definitely appreciate the restaurants. Tourists can also enjoy the city's shopping and sporting events. In Windsor, there are 5 hotels and other accommodation options to choose from. Find out more about Windsor.

What are the top places to visit in Windsor?

A favourite place to visit is Mousehouse Cheesehaus. You'll also find East Towne Mall and Olbrich Botanical Gardens in the area. Take a look at what more there is to see and do in Expedia's Windsor guide.

What's the weather like in Windsor?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Windsor are January, December, March and November, with each month seeing an average of 22 cm of snowfall.

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Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, WI from Rp1.226.208

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

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Our top choices for Windsor hotels

1. Days Inn by Wyndham Madison NE/Windsor

2. Super 8 by Wyndham Windsor/Madison North

3. Holiday Inn Express Deforest (Madison Area) by IHG

4. Comfort Inn & Suites Madison North

5. DoubleTree by Hilton Madison East

6. La Quinta Inn & Suites by Wyndham Madison American Center

7. Cambria Hotel Madison East

8. Holiday Inn Madison at The American Center by IHG

9. Fairfield Inn & Suites by Marriott Madison East

10. Hilton Garden Inn Madison Sun Prairie

11. The Madison Concourse Hotel and Governor's Club

12. DoubleTree by Hilton Madison Downtown

13. Holiday Inn Express & Suites Madison by IHG

14. The Edgewater

15. Hampton Inn Madison East Towne Mall Area

16. Courtyard by Marriott Madison East

17. Best Western Plus InnTowner Madison

18. Best Western East Towne Suites

19. Quality Inn & Suites Sun Prairie Madison East

20. SpringHill Suites by Marriott Madison

Stay near popular Windsor attractions

Mousehouse Cheesehaus

Learn more about Windsor

Top Windsor Hotel Reviews

The Madison Concourse Hotel and Governor's Club

Best Western Premier Park Hotel

DoubleTree by Hilton Madison East

AmericInn by Wyndham Madison West

Hampton Inn & Suites Madison-West

Baymont by Wyndham Madison West/Middleton WI West

Days Inn & Suites by Wyndham Madison

DoubleTree by Hilton Madison Downtown

More cheap stays in Windsor

Motel 6 Madison, WI - East

Baymont Inn & Suites by Wyndham Madison

Econo Lodge Madison East

Baymont by Wyndham Madison West/Middleton WI West

Super 8 by Wyndham Madison South

Comfort Suites Madison West - Middleton

Frequently asked questions

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