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

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor holiday homes

A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

1. 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 AU$360
includes taxes & fees
26 Oct - 27 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
Master Bedroom /King bed

2. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (26 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 AU$894
includes taxes & fees
19 Nov - 20 Nov
Entire 3 Bedroom with Fireplace - sleeps 12
Room

3. 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 AU$853
includes taxes & fees
19 Nov - 20 Nov
Charming 3-bedroom house on Madison's Eastside! Close to everything!
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

4. 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 AU$629
includes taxes & fees
25 Oct - 26 Oct
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A dining area with a wooden table and chairs, a window with blinds, and a view of a wooden fence.

5. #4 Riverfront Lodging. Beach, Boat, Fish, Hike.

#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
9.0 out of 10, Wonderful, (2 reviews)
"Amazing view, clean stay and pet friendly for those with fur babies. Will definitely be coming back!"
United States
Miranda
The price is AU$349
includes taxes & fees
27 Oct - 28 Oct
#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
A two-story house with a large front lawn and a body of water in the background.

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

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is AU$363
includes taxes & fees
27 Oct - 28 Oct
Riverfront Lodging. Beach, hike, ski, explore, relax. #1
A cozy cabin interior with a wooden ceiling, a large window, a dining area, and a seating area with a chair and sofa.

7. COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!
Lodi
10.0 out of 10, Exceptional, (115 reviews)
"Beautiful view! Nice features all around!"
United States
Tim
The price is AU$579
includes taxes & fees
9 Nov - 10 Nov
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!
A living room with two grey sofas, a patterned rug, and a kitchen in the background.

8. Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.2 out of 10, Very good, (20 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is AU$705
includes taxes & fees
25 Oct - 26 Oct
Waters Edge Cottage
A grassy area with a tree, a small rock formation, and a distant structure.

9. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is AU$363
includes taxes & fees
9 Nov - 10 Nov
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

10. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (46 reviews)
"Great place!"
United States
Robert F.
The price is AU$794
includes taxes & fees
28 Oct - 29 Oct
Doty ★ Walk to Everything -Hotel Quality- Downtown
A deck with a table and chairs, overlooking a grassy area with trees and a body of water.

11. Riverfront Lodging. Beach, hike, ski, explore, relax. #2

Riverfront Lodging. Beach, hike, ski, explore, relax. #2
Dekorra
10.0 out of 10, Exceptional, (1 review)
"Great stay for our fishing trip"
United States
Brian S.
The price is AU$405
includes taxes & fees
3 Nov - 4 Nov
Riverfront Lodging. Beach, hike, ski, explore, relax. #2
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

8/10 Good
"It’s downtown. Easy to walk to either lake."
christine isabelle 2-night trip
Posted 13 hours ago
The Madison Concourse Hotel and Governor's Club

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
206
Accommodation
104 Holiday Homes
Lowest Price
AU$349
Highest Price
AU$894