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

Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor vacation rentals

A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (194 reviews)
"Good location"
United States
ANCA
The price is AED 410
AED 474 total
includes taxes & fees
10 Nov - 11 Nov
The Dylin
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)
The price is AED 298
AED 980 total
includes taxes & fees
13 Oct - 14 Oct
Studio Apartment at Cannery Square
A horse and foal in a fenced pasture with trees and open fields in the background.

3. 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 AED 544
AED 913 total
includes taxes & fees
17 Oct - 18 Oct
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.

4. 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)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is AED 466
AED 1,302 total
includes taxes & fees
19 Oct - 20 Oct
2 Bed, 2 Bath 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.

5. 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.
The price is AED 466
AED 1,306 total
includes taxes & fees
13 Oct - 14 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A gym with treadmills, elliptical machines, and free weights.

6. 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.
Studio Apartment at Cannery Square
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

7. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (56 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
A Room with a View
A modern kitchen with a refrigerator, microwave, and bar stools.

8. 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.
2 Bedroom Apartment Downtown Sun Prairie!
An outdoor seating area with wicker furniture and a central fire feature.

9. 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.
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
An outdoor patio with a brick grill and seating area.

10. 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.
The price is AED 491
AED 647 total
includes taxes & fees
1 Nov - 2 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A chalkboard sign with a welcome message and room instructions.

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, (24 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is AED 1,286
AED 2,194 total
includes taxes & fees
1 Nov - 2 Nov
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
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.

12. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (57 reviews)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
The price is AED 1,329
AED 2,259 total
includes taxes & fees
3 Nov - 4 Nov
Capital City- 6 Miles from Madison with fireplace
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

13. 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, (17 reviews)
"Beautiful place, great stay."
United States
Thomas D.
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Master Bedroom /King bed

14. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (24 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 AED 1,377
AED 2,318 total
includes taxes & fees
1 Nov - 2 Nov
Entire 3 Bedroom with Fireplace - sleeps 12
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

15. 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)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is AED 520
AED 1,595 total
includes taxes & fees
1 Nov - 2 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

16. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is AED 585
AED 756 total
includes taxes & fees
9 Nov - 10 Nov
Pool with Slide. Great for Business Travelers!
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

17. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (46 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is AED 657
AED 1,248 total
includes taxes & fees
14 Oct - 15 Oct
Updated home with lake views, across the street from Lake WI, near free ferry
A grassy area with a tree, a small rock formation, and a distant structure.

18. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is AED 528
AED 928 total
includes taxes & fees
27 Oct - 28 Oct
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
A hallway with wooden paneling, a framed welcome sign, and a door leading to a room.

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

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is AED 528
AED 975 total
includes taxes & fees
4 Nov - 5 Nov
Riverfront Lodging. Beach, hike, ski, explore, relax. #1
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

20. 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
The price is AED 663
AED 861 total
includes taxes & fees
25 Oct - 26 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Dylin

The Dylin

10/10 Excellent
"We stayed at the Dylin for parents weekend and it was perfect. Great location, underground parking, very clean, fully stocked kitchen comfy living space with separate bedroom. We will definitely be back"
michelle 2-night trip
Posted 5 hours ago
The Dylin

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.