Vacation rentals in Windsor
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Top-rated vacation rentals in Windsor
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windsor vacation rentals
Other great vacation rentals in Windsor
Guest favourite
Cottage in Windsor
5.0 out of 5 average rating, 121 reviewsVineyard Cozy Cottage & Hot Tub
Jan. 2 – 9
$430 CAD per night
Guest favourite
Home in Windsor
5.0 out of 5 average rating, 100 reviewsLarge Home w/ HotTub 10 min to Downtown Healdsburg
Sep. 6 – 13
$959 CAD per night
Guest favourite
Guesthouse in Santa Rosa
4.96 out of 5 average rating, 169 reviewsKV garden Cottage.
Jan. 4 – 11
$186 CAD per night
Guest favourite
Home in Windsor
4.99 out of 5 average rating, 101 reviewsGorgeous Victorian in the HEART of Windsor
Dec. 23 – 30
$745 CAD per night
Guest favourite
Guesthouse in Sebastopol
4.96 out of 5 average rating, 301 reviewsArbor View
Jul. 13 – 20
$185 CAD per night
Guest favourite
Apartment in Sebastopol
4.99 out of 5 average rating, 608 reviewsAmy's Local BNB - walk to town **and hot tub!**
Oct. 11 – 18
$255 CAD per night
Guest favourite
Guesthouse in Santa Rosa
4.89 out of 5 average rating, 260 reviewsCentral Santa Rosa Garden Getaway
Oct. 1 – 8
$173 CAD per night
Guest favourite
Guest suite in Santa Rosa
4.97 out of 5 average rating, 181 reviewsWine Country Retreat
Jan. 25 – Feb. 1
$234 CAD per night
Quick stats about vacation rentals in Windsor
Total rentals
350 properties
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Rentals with a pool
230 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
12K reviews
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