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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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, (2 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is NZ$419
includes taxes & fees
7 Sept - 8 Sept
Escape to tranquility – your countryside haven, and at times with a horse or two

2. 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.
The price is NZ$1,058
includes taxes & fees
7 Sept - 8 Sept
Entire 3 Bedroom with Fireplace - sleeps 12
A sunroom with wicker furniture, large windows, and string lights.

3. 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.
The price is NZ$1,256
includes taxes & fees
8 Sept - 9 Sept
Hot Tub - Game Room - 20 min to Capitol - Pets
A modern living room with a fireplace, a flat-screen TV displaying 'NETFLIX', and a cozy seating arrangement.

4. 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.
The price is NZ$1,127
includes taxes & fees
17 Sept - 18 Sept
Hot Tub - King Suite - Game Room - Large Groups
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

5. 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, (16 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is NZ$857
includes taxes & fees
4 Oct - 5 Oct
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

6. 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.
The price is NZ$863
includes taxes & fees
20 Sept - 21 Sept
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A two-story building with a central driveway leading to a gated entrance.

7. #4 Riverfront Lodging. Beach, Boat, Fish, Hike.

#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is NZ$459
includes taxes & fees
7 Sept - 8 Sept
#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

8. Updated home with lake views, across the street from Lake Wisc!

Updated home with lake views, across the street from Lake Wisc!
Merrimac
10.0 out of 10, Exceptional, (43 reviews)
"Had a great time staying here very nice little house"
United States
Paul W.
The price is NZ$560
includes taxes & fees
7 Sept - 8 Sept
Updated home with lake views, across the street from Lake Wisc!
A room with a window, a green headboard, a beige sofa, and two framed posters on the wall.

9. 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 NZ$496
includes taxes & fees
9 Sept - 10 Sept
Riverfront Lodging. Beach, hike, ski, explore, relax. #2
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, (45 reviews)
"Great place!"
United States
Robert F.
The price is NZ$948
includes taxes & fees
7 Sept - 8 Sept
Doty ★ Walk to Everything -Hotel Quality- Downtown
A spacious living room with a fireplace, a large TV mounted on a stone wall, and a dining area with a kitchen in the background.

11. Campus-Area 4BR | Panoramic Bluffs

Campus-Area 4BR | Panoramic Bluffs
Fitchburg
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
The price is NZ$1,284
includes taxes & fees
7 Sept - 8 Sept
Campus-Area 4BR | Panoramic Bluffs
A wooden dining table with a metal basket centerpiece, large windows with a view of the sea, and a gray sofa in a room with wooden paneling.

12. Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.2 out of 10, Very good, (18 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is NZ$859
includes taxes & fees
15 Sept - 16 Sept
Waters Edge Cottage
A cozy room with a wooden wall, a sofa, a coffee table, a ceiling fan, and a window.

13. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is NZ$459
includes taxes & fees
8 Sept - 9 Sept
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
An outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and a body of water.

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

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is NZ$490
includes taxes & fees
9 Sept - 10 Sept
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

Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

8/10 Good
"Don't play the games, they wait until after 3 pm the following day after everyone has left to pay any winnings. There was a note on the end machine that states it could be upto 48 hours for payment but if you don't notice it because of where they are located you won't get the money."
STANLEY 1-night trip
Posted less than an hour ago
Baymont by Wyndham Madison West/Middleton WI West

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
253
Accommodation
102 Holiday Homes
Lowest Price
NZ$419
Highest Price
NZ$1,284