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Search results; Over 1,000 homes in Windsor

Top guest favourite
Flat in Windsor
Pool + 4 Hot Tubs! Gym, Luxury 2 bedroom villa.
2 bedrooms, 4 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.97 out of 5 average rating, 113 reviews
Apartment in Windsor
WorldMark Windsor Two-Bedroom Condo
2 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.4 out of 5 average rating, 53 reviews
Room in Windsor
Beautiful Windsor Resort - Spacious 1 Bedroom Unit
2 beds, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Room in Windsor
Rivermind, a Wine Country Retreat #1
1 queen bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 168 reviews
Flat in Windsor
Enjoy Wine Country
2 bedrooms, 1 queen bed, 2 bathrooms
20–25 Sept
Top guest favourite
Room in Windsor
Wine Country Stay
1 queen bed, 1 bathroom
7–12 Sept
4.9 out of 5 average rating, 214 reviews
Guest favourite
Flat in Windsor
Exemplary Windsor 2 Bedroom +Amenities!
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 22 reviews
Guest favourite
Flat in Windsor
Windsor/Sonoma 2 Bed/2 Bath Condo Resort ~ Pool ~
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Windsor
Make This Your Best Vacation Ever - 2 Bdrm Condo
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 59 reviews
Top guest favourite
Home in Windsor
The Gilded Bungalow • walk to town green • hot tub
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Windsor
Gourmet Kitchen in Wine Country w/Hot Tub + Office
4 bedrooms, 7 beds, 2.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 116 reviews
Guest favourite
Rooms in Windsor
Two-room suite for 1-4 guests
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 54 reviews
Room in Santa Rosa
2 Queens w/ Kitchenette in Sonoma Wine Country
2 queen beds, 1 bathroom
7–12 Sept
4.61 out of 5 average rating, 70 reviews
Guest favourite
Flat in Windsor
Wine Country 2 Bedroom Sleeps 6!
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 95 reviews
Top guest favourite
Home in Windsor
Winelight Vineyard Home With Spa
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 445 reviews
Top guest favourite
Home in Windsor
Wine Country Retreat: Pool, Hot Tub, Views & EV
4 bedrooms, 6 beds, 3 bathrooms
21–26 Sept
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Windsor
Gorgeous Victorian in the HEART of Windsor
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 134 reviews
Superhost
Flat in Windsor
Perfect Windsor 1 Bedroom! +Amenities!
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Santa Rosa
Cozy Wine Country Escape
1 queen bed, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 194 reviews