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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Windsor vacation rentals

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

1. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very Good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
$244 nightly
The price is $275
Sep 9 - Sep 10
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.

2. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (29 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
$331 nightly
The price is $372
Oct 4 - Oct 5
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.

3. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very Good, (1 review)
$263 nightly
The price is $280
Oct 4 - Oct 5
Total with taxes and fees
Studio Apartment at Cannery Square
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

4. 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
Sep 9 - Sep 10
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

5. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.8 out of 10, Exceptional, (54 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$355 nightly
The price is $399
Sep 20 - Sep 21
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
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, (181 reviews)
"The freaking best place."
United States
Seth
$147 nightly
The price is $170
Sep 9 - Sep 10
Total with taxes and fees
The Dylin
A modern kitchen with a refrigerator, microwave, and bar stools.

7. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 reviews)
"This is the third time we have rented this property. Love the full kitchen and laundry! Comfy bed. Experience was great. Especially like the pizza shop on main level and coffe shop across the street!"
United States
Robert M.
$361 nightly
The price is $406
Sep 14 - Sep 15
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

8. 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
An outdoor patio with a brick grill and seating area.

9. 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)
"Great place for a stay."
United States
Andy D.
$157 nightly
The price is $179
Sep 20 - Sep 21
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A chalkboard sign with a welcome message and room instructions.

10. 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, (21 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
$530 nightly
The price is $596
Sep 9 - Sep 10
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A hotel pantry with a refrigerator stocked with beverages, a microwave, and shelves with snacks and condiments.

11. Accessible 1BR Suite | Free Daily Breakfast & Pool

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
$216 nightly
The price is $249
Oct 4 - Oct 5
Total with taxes and fees
Accessible 1BR Suite | Free Daily Breakfast & Pool
A sunroom with wicker furniture, large windows, and string lights.

12. Hot Tub - Game Room - 20 min to Capitol - Pets

Hot Tub - Game Room - 20 min to Capitol - Pets
Sun Prairie
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! Thank you!!"
United States
Goodie A.
Hot Tub - Game Room - 20 min to Capitol - Pets

13. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (21 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.
$559 nightly
The price is $629
Sep 9 - Sep 10
Total with taxes and fees
Entire 3 Bedroom with Fireplace - sleeps 12
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.

14. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (54 reviews)
"Very nice place"
United States
Penny C.
$595 nightly
The price is $669
Sep 9 - Sep 10
Total with taxes and fees
Capital City- 6 Miles from Madison with fireplace
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
$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 spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

16. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (14 reviews)
"This property is the nicest property we have stayed in. Everything was there for our convenience. It was extremely pet friendly and very nicely furnished. We hope to stay there again."
United States
Donald V.
$206 nightly
The price is $227
Sep 14 - Sep 15
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (17 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$446 nightly
The price is $506
Oct 4 - Oct 5
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.

18. 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.
$126 nightly
The price is $132
Sep 9 - Sep 10
Total with taxes and fees
A Room with a View
A modern living room with a fireplace, a flat-screen TV displaying 'NETFLIX', and a cozy seating arrangement.

19. Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
$575 nightly
The price is $612
Sep 9 - Sep 10
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

20. 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.
$429 nightly
The price is $487
Sep 21 - Sep 22
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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

Embassy Suites By Hilton Madison Downtown

Embassy Suites By Hilton Madison Downtown

10/10 Excellent
"Very comfortable and clean room. Staff was nice and friendly."
Aisha 1-night trip
Posted less than an hour ago
Embassy Suites By Hilton 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 $132 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?

LakeMonona Waterfront + PrivateDock + FencedYard + HotTub + GameRoom + EVCharger: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a balcony, and a barbecue grill 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. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

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 Barrymore Theatre.

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.