Windsor Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Windsor vacation homes
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 twoDane
10.0 out of 10, Exceptional, (1 review)
"We had a great stay! Everything was as advertised and the sunset on the patio was the highlight."
Michelle M.
The price is CA $259
CA $417 total
includes taxes & fees
Aug 11 - Aug 12
Entire 3 Bedroom with Fireplace - sleeps 12
Entire 3 Bedroom with Fireplace - sleeps 12Sun Prairie
9.8 out of 10, Exceptional, (19 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 "
Steve S.
The price is CA $491
CA $847 total
includes taxes & fees
Jul 21 - Jul 22
Hot Tub - King Suite - Game Room - Large Groups
Hot Tub - King Suite - Game Room - Large GroupsSun Prairie
10.0 out of 10, Exceptional, (21 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
George P.
The price is CA $421
CA $1,193 total
includes taxes & fees
Jul 29 - Jul 30
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Bright, Private 3BR Duplex Unit with Parking in Cottage GroveVillage of Cottage Grove
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
Marisa P.
The price is CA $306
CA $779 total
includes taxes & fees
Aug 11 - Aug 12
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, (52 reviews)
"Great little lake house, close to downtown Madison. "
LiHsin C.
The price is CA $418
CA $808 total
includes taxes & fees
Aug 3 - Aug 4
Doty ★ Walk to Everything -Hotel Quality- Downtown
Doty ★ Walk to Everything -Hotel Quality- DowntownDowntown Madison
9.8 out of 10, Exceptional, (44 reviews)
"The house was super clean and well stocked, and very comfortable. Great location, easy to walk everywhere we wanted to go. Street parking was a little hard to find on the weekend, but parking garages were close and very reasonably priced. We would definitely stay here again "
Deborah G.
The price is CA $602
CA $879 total
includes taxes & fees
Jul 26 - Jul 27
Golden Days | Madison Living
Golden Days | Madison LivingFitchburg
10.0 out of 10, Exceptional, (25 reviews)
"We enjoyed staying here. VERY nice house, easy access, clean, a lot of space, no issues. We would book here again!"
Liz A.
The price is CA $529
CA $1,227 total
includes taxes & fees
Jul 20 - Jul 21
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
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor Hotel Reviews
Hampton Inn & Suites Madison / Downtown
10/10 Excellent
Find out more about Windsor
Windsor Vacation Homes information
Number of reviews | 7,624 |
|---|---|
Accommodation | 104 Vacation Homes |
Lowest Price | CA $98 |
Highest Price | CA $171 |
Explore a world of travel with Expedia
- Vacation Homes in Wisconsin Dells
- Cottages in Beaver Dam
- Resorts in Elkhorn
- Cabin Rentals in Wisconsin Dells
- Farmstay in Reedsburg
- B&B in Marshall
- Cabin Rentals in Whitewater
- Resorts in Wisconsin Dells
- Motels in Dodge County
- Hilton Hotels in Windsor
- Cabin Rentals in Marshall
- Cabin Rentals in Endeavor
- Hostels in Windsor
- Rv Parks in Wisconsin Dells
- Token Creek Hotels
- Resorts in Edgerton
- Aparthotels in Riley
- Motels in Arena
- Condo Rentals in Stoughton
- Cabin Rentals in Edgerton
- Hotels near Dane County Regional
- Motels in Watertown
- B&B in Dalton
- B&B in Portage
- Cabin Rentals in Fall River
- Hostels in Watertown
- Motels in Madison
- B&B in Montello
- Chalets in Dane County
- Madison Hotels
- B&B in Endeavor
- Chalets in Waunakee
- Farmstay in Sun Prairie
- Cottages in Janesville
- Flights from Montreal (YUL) to Madison (MSN)
- Alaska Airlines San Diego (SAN) to Madison (MSN) flights
- Flights from Duluth (DLH) to Madison (MSN)
- Flights from Galena (GAL) to Madison (MSN)
- Flights from Toronto (YYZ) to Madison (MSN)
- Flights from Ogdensburg (OGS) to Madison (MSN)
- Flights to Madison
- Flights from Burlington (BTV) to Madison (MSN)
- Flights from Moncton (YQM) to Madison (MSN)
- Flights from Plattsburgh (PBG) to Madison (MSN)
- Flights from Great Falls (GTF) to Madison (MSN)
- Flights from Minneapolis (MSP) to Madison (MSN)
- Flights from Saskatoon (YXE) to Madison (MSN)
- Flights from Dane County Regional
- Flights from Colorado Springs (COS) to Madison (MSN)
- Flights from Regina (YQR) to Madison (MSN)
- Flights from Winnipeg (YWG) to Madison (MSN)
- Flights from Toronto (YTO) to Madison (MSN)
- Flights from Kingston (KIN) to Madison (MSN)
- Flights from London (YXU) to Madison (MSN)
- Flights from Edmonton (YEG) to Madison (MSN)
- Air Canada Halifax (YHZ) to Madison (MSN) flights
- Flights from Bedford (BED) to Madison (MSN)
- Flights from Québec (YQB) to Madison (MSN)
- Flights from Hamilton (YHM) to Madison (MSN)
- Flights from Kitchener (YKF) to Madison (MSN)
- Flights from London (LHR) to Madison (MSN)
- Flights from Ottawa (YOW) to Madison (MSN)
- Flights from Fargo (FAR) to Madison (MSN)
- Flights from Atlanta (ATL) to Madison (MSN)
- Flights from Sault Ste. Marie (YAM) to Madison (MSN)
- Flights from Manila (MNL) to Madison (MSN)
- Flights from Thunder Bay (YQT) to Madison (MSN)
- Flights from Vancouver (YVR) to Madison (MSN)
- Flights from Ontario Intl. Airport (ONT) to Madison (MSN)
- Flights from Halifax (YHZ) to Madison (MSN)
- Flights from Seattle (SEA) to Madison (MSN)
- Flights from St. John's (YYT) to Madison (MSN)
- Flights from Bellingham (BLI) to Madison (MSN)
- Flights from Detroit (DTW) to Madison (MSN)
- Flights to Windsor
- Flights from Minot (MOT) to Madison (MSN)
- Flights from Sault Ste. Marie (CIU) to Madison (MSN)
- Flights from Toronto (YTZ) to Madison (MSN)
- Flights from Bangor (BGR) to Madison (MSN)
- Flights from Fredericton (YFC) to Madison (MSN)
- Flights from Phoenix (PHX) to Madison (MSN)
- Flights from North Bay (YYB) to Madison (MSN)
- Flights from Buffalo (BUF) to Madison (MSN)
- Flights from Chicago (ORD) to Madison (MSN)
- Flights from Calgary (YYC) to Madison (MSN)
- Flights from Danbury (DXR) to Madison (MSN)
- Air Canada Fredericton (YFC) to Madison (MSN) flights
- Flights from Kingston (YGK) to Madison (MSN)
- Flights from Grand Forks (GFK) to Madison (MSN)
- Flights from Mexico City (MEX) to Madison (MSN)
- Flights from Peterborough (YPQ) to Madison (MSN)
- Flights from Kelowna (YLW) to Madison (MSN)
- Flights from Niagara Falls (IAG) to Madison (MSN)
- Flights from Victoria (YYJ) to Madison (MSN)
- Flights from Boston (BOS) to Madison (MSN)
- Flights from Presque Isle (PQI) to Madison (MSN)
- Flights from Whitehorse (YXY) to Madison (MSN)
- Flights from Mankato (MKT) to Madison (MSN)