Windsor Vacation Rentals

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Check prices for these dates

Our top choices for Windsor vacation rentals

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (216 reviews)
"Good location"
United States
ANCA
The price is CA $156
CA $180 total
includes taxes & fees
Nov 19 - Nov 20
The Dylin

2. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is CA $115
CA $361 total
includes taxes & fees
Nov 15 - Nov 16
Studio Apartment at Cannery Square

3. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.6 out of 10, Excellent, (17 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
The price is CA $165
CA $375 total
includes taxes & fees
Nov 15 - Nov 16
Studio Apartment at Cannery Square

4. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is CA $180
CA $480 total
includes taxes & fees
Nov 13 - Nov 14
2 Bed, 2 Bath Apartment at Cannery Square

5. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is CA $181
CA $483 total
includes taxes & fees
Nov 29 - Nov 30
2 Bed, 2 Bath Apartment at Cannery Square

6. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is CA $122
CA $177 total
includes taxes & fees
Dec 2 - Dec 3
A Room with a View

7. 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.
The price is CA $282
CA $358 total
includes taxes & fees
Nov 29 - Nov 30
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

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, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is CA $244
CA $378 total
includes taxes & fees
Dec 1 - Dec 2
Escape to tranquility – your countryside haven, and at times with a horse or two

9. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (43 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.
The price is CA $274
CA $552 total
includes taxes & fees
Nov 15 - Nov 16
2 Bedroom Apartment Downtown Sun Prairie!

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

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.4 out of 10, Very good, (7 reviews)
"Great place for a stay."
United States
Andy D.
The price is CA $208
CA $260 total
includes taxes & fees
Nov 15 - Nov 16
King Suite | Free Breakfast. Pool and Hot Tub

11. 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, (26 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is CA $497
CA $816 total
includes taxes & fees
Nov 13 - Nov 14
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

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

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
The price is CA $282
CA $349 total
includes taxes & fees
Nov 29 - Nov 30
Accessible 1BR Suite | Free Daily Breakfast & Pool

13. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (58 reviews)
"Great stay."
United States
Kevin M.
The price is CA $513
CA $836 total
includes taxes & fees
Nov 17 - Nov 18
Capital City- 6 Miles from Madison with fireplace

14. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is CA $175
CA $317 total
includes taxes & fees
Dec 7 - Dec 8
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.

15. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (27 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
The price is CA $479
CA $792 total
includes taxes & fees
Nov 15 - Nov 16
Entire 3 Bedroom with Fireplace - sleeps 12

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

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is CA $173
CA $308 total
includes taxes & fees
Nov 16 - Nov 17
Riverfront Lodging. Beach, hike, ski, explore, relax. #1

17. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is CA $232
CA $294 total
includes taxes & fees
Nov 15 - Nov 16
Pool with Slide. Great for Business Travelers!

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is CA $433
CA $551 total
includes taxes & fees
Dec 6 - Dec 7
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

19. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is CA $511
CA $782 total
includes taxes & fees
Nov 20 - Nov 21
Charming 3-bedroom house on Madison's Eastside! Close to everything!

20. 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, (20 reviews)
"Everything was very nice"
United States
Anonymous traveller
The price is CA $210
CA $597 total
includes taxes & fees
Nov 16 - Nov 17
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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.

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $156 per night. Entering your travel dates in the search wizard 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.