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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windsor vacation rentals

A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

1. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (55 reviews)
$314 nightly
The price is $353
Oct 21 - Oct 22
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

2. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
$254 nightly
The price is $270
Oct 4 - Oct 5
Total with taxes and fees
Studio Apartment at Cannery Square
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

3. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
$313 nightly
The price is $352
Oct 4 - Oct 5
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

4. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
$217 nightly
The price is $251
Oct 4 - Oct 5
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A modern kitchen with a refrigerator, microwave, and bar stools.

5. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 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
Sha'Vonne G.
$345 nightly
The price is $388
Oct 4 - Oct 5
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

6. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (187 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
$117 nightly
The price is $135
Oct 25 - Oct 26
Total with taxes and fees
The Dylin
A chalkboard sign with a welcome message and room instructions.

7. Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (23 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
$533 nightly
The price is $600
Sep 29 - Sep 30
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

8. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (2 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
$225 nightly
The price is $249
Oct 13 - Oct 14
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A bedroom with a dark grey wall, a bed with a striped bedspread, multiple pillows, a small side table with a vase and a lamp, and two framed botanical prints on the wall.

9. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (56 reviews)
"Very nice place"
United States
Penny C.
$597 nightly
The price is $672
Sep 27 - Sep 28
Total with taxes and fees
Capital City- 6 Miles from Madison with fireplace

10. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"Tami was a wonderful host! Check in was fast and she was easy to communicate with. The house was clean and spacious."
United States
Joanna C.
$560 nightly
The price is $630
Oct 4 - Oct 5
Total with taxes and fees
Entire 3 Bedroom with Fireplace - sleeps 12
An outdoor patio with a brick grill and seating area.

11. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
$157 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

12. Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
$308 nightly
The price is $357
Oct 4 - Oct 5
Total with taxes and fees
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

13. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$430 nightly
The price is $489
Oct 20 - Oct 21
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

14. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$117 nightly
The price is $124
Sep 29 - Sep 30
Total with taxes and fees
A Room with a View
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

15. Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 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
Joy E.
$308 nightly
The price is $357
Oct 4 - Oct 5
Total with taxes and fees
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

16. Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
$452 nightly
The price is $512
Oct 8 - Oct 9
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A cozy room with a wooden wall, a sofa, a coffee table, a ceiling fan, and a window.

17. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
$243 nightly
The price is $252
Sep 29 - Sep 30
Total with taxes and fees
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

18. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$172 nightly
The price is $195
Oct 4 - Oct 5
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

19. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
$195 nightly
The price is $221
Oct 11 - Oct 12
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and a body of water.

20. Riverfront Lodging. Beach, hike, ski, explore, relax. #1

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
$262 nightly
The price is $272
Sep 29 - Sep 30
Total with taxes and fees
Riverfront Lodging. Beach, hike, ski, explore, relax. #1
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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Top Windsor Hotel Reviews

Moxy Madison Downtown

Moxy Madison Downtown

10/10 Excellent
"Staff was super helpful and kind."
Tina 2-night trip
Posted 3 hours ago
Moxy Madison Downtown

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 $124 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.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Mousehouse Cheesehaus, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers say Windsor has a good selection of restaurants. Make sure you have time to check out the shopping and sporting events during your trip.

What's the top vacation rental that Windsor has to offer?

Doty ★ Walk to Everything -Hotel Quality- Downtown: Visitors like this Windsor vacation home rental. It is located in the city center and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Windsor?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Mousehouse Cheesehaus, or get out into nature at a spot like Olbrich Botanical Gardens. In the larger area, you’ll find East Towne Mall and Madison Area Technical College.

What are vacation rentals like in Windsor?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.