Title: Windsor Oaks Vineyards in Windsor - Tours and Activities | Expedia.ca [Windsor Oaks Vineyards Hotels](https://expedia.ca/Windsor-Oaks-Vineyards-Hotels.0-l6327443-0.Travel-Guide-Filter-Hotels)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d9542.Travel-Guide-Flights)[Things to do in Windsor](https://expedia.ca/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)[Windsor Oaks Vineyards Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor-Oaks-Vineyards.d6327443.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d9542.Destination-Travel-Guides) # Windsor Oaks Vineyards Tours and Activities ## Visit Windsor Oaks Vineyards Activities [Windsor travel guide](https://expedia.ca/Windsor.dx9542) --- --- ## Plan a trip to see Windsor Oaks Vineyards Price found within the past 48 hours. Click for updated prices. ![Elm House Inn](https://images.trvl-media.com/lodging/7000000/6930000/6924700/6924685/20d86e6f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Elm House Inn Central Napa CA $813 per person May 28 - May 31 found 22 hours ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 9.6/10 Exceptional! (1,505 reviews) Cute place; I have stayed here twice and would come back. Nice coffee bar; lovely staff...who called me right away to let me know I had left something behind. Clean and comfortable! Reviewed on Mar 5, 2026 ![Sonesta Emeryville - San Francisco Bay Bridge](https://images.trvl-media.com/lodging/1000000/560000/551100/551060/472c4721_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sonesta Emeryville - San Francisco Bay Bridge CA $1,030 per person May 21 - May 25 found 8 hours ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 8.6/10 Excellent! (1,375 reviews) Very friendly helpful staff , room clean , other amenities out of order like the ice machine , our heater wasn’t working and i have a anemic child which i was Told the room would be changed never did Reviewed on Mar 8, 2026 ![Claremont Resort & Club](https://images.trvl-media.com/lodging/1000000/10000/6700/6609/ba76b95f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Claremont Resort & Club Claremont Hills CA $1,462 per person Apr 21 - Apr 23 found 3 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Oakland (OAK) 8.8/10 Excellent! (1,007 reviews) Great stay and property Reviewed on Mar 8, 2026 ### Tours & day trips [See all 13 activities](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=ToursDayTrips) ![Safari West Sonoma Adventure Tour](https://mediaim.expedia.com/localexpert/50905278/33e23bec-d47d-4022-a928-15f72ec55614.jpg?impolicy=resizecrop&rw=500&rh=280) ### Safari West Sonoma Adventure Tour 3h Free cancellation available CA $149 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/safari-west-sonoma-adventure-tour.a50905278.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Classic Safari Adventure at Safari West](https://mediaim.expedia.com/localexpert/50754106/dbf846b5-e128-43a2-afe2-f2cbfc91f9d9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Classic Safari Adventure at Safari West 3h Free cancellation available CA $149 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/classic-safari-adventure-at-safari-west.a50754106.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Icon Wine & Food Pairing at Williamson Wines in Healdsburg](https://mediaim.expedia.com/localexpert/674597/a5e5b634-bbd9-45cf-abb9-ecde2c3f9a0d.jpg?impolicy=resizecrop&rw=500&rh=280) ### Icon Wine & Food Pairing at Williamson Wines in Healdsburg 1h 30m 9.6/10 26 Viator reviews Free cancellation available CA $68 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/icon-wine-food-pairing-experience-at-williamson-wines-in-healdsburg.a674597.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Healdsburg Wine and Food Pairing Guided Walking Tour](https://mediaim.expedia.com/localexpert/2160900/a9a08d53-fff5-4e22-b145-5995c474ae04.jpg?impolicy=resizecrop&rw=500&rh=280) ### Healdsburg Wine and Food Pairing Guided Walking Tour 4h 10/10 90 Viator reviews Free cancellation available CA $189 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/healdsburg-wine-tasting-and-food-pairing-guided-walking-tour.a2160900.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Hidden Sonoma County: Redwoods, Cheese, Coast, and Artisan Picnic](https://mediaim.expedia.com/localexpert/49371162/ca535615-e8ae-4d89-9765-b471b9f362f7.jpg?impolicy=resizecrop&rw=500&rh=280) ### Hidden Sonoma County: Redwoods, Cheese, Coast, and Artisan Picnic 6h 10/10 2 Viator reviews Free cancellation available CA $351 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/hidden-gems-adventure-in-west-sonoma-county.a49371162.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![History Walking Tour of Healdsburg](https://mediaim.expedia.com/localexpert/44619999/cbefff56-05ae-409f-96d9-7d58ce9a1052.jpg?impolicy=resizecrop&rw=500&rh=280) ### History Walking Tour of Healdsburg 1h 30m 10/10 7 Viator reviews Free cancellation available CA $61 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/history-walking-tour-of-healdsburg.a44619999.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Healdsburg: Guided Electric Bike Wine Tour with Winery Stops](https://mediaim.expedia.com/localexpert/50142620/c8a9252c-e7c9-4355-b030-8b79de7b8233.jpg?impolicy=resizecrop&rw=500&rh=280) ### Healdsburg: Guided Electric Bike Wine Tour with Winery Stops 4h+ 10/10 3 GetYourGuide reviews Free cancellation available CA $229 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/sonoma-guided-e-bike-wine-tour-with-winery-stops.a50142620.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4](https://mediaim.expedia.com/localexpert/48379179/f90a5ed5-82de-4c82-bad8-17381e5015cf.jpg?impolicy=resizecrop&rw=500&rh=280) ### Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4 6h 10/10 1 verified review Free cancellation available CA $813 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/6-hours-healdsburg-wine-tour-with-luxury-suv.a48379179.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Half Day Guided Electric Bike Wine Tasting Tour with Lunch](https://mediaim.expedia.com/localexpert/50906958/17e063ab-bcef-417d-9128-cf08fd631a4e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Half Day Guided Electric Bike Wine Tasting Tour with Lunch 4h 10/10 1 verified review Free cancellation available CA $243 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/half-day-guided-electric-bike-wine-tasting-tour-with-lunch.a50906958.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Full Day Guided Electric Bike Wine Tasting Tour with Lunch](https://mediaim.expedia.com/localexpert/48963166/e7cf40c0-4dff-4dc8-9188-2d0df8002084.jpg?impolicy=resizecrop&rw=500&rh=280) ### Full Day Guided Electric Bike Wine Tasting Tour with Lunch 6h 10/10 2 Viator reviews Free cancellation available CA $324 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/guided-electric-bike-wine-tour-through-sonoma-county.a48963166.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ### Private & custom tours [See all 3 activities](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=Privatecustomtours) ![Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4](https://mediaim.expedia.com/localexpert/48379179/f90a5ed5-82de-4c82-bad8-17381e5015cf.jpg?impolicy=resizecrop&rw=500&rh=280) ### Healdsburg 6 Hour Wine Tour with Luxury SUV - Seats up to 4 6h 10/10 1 verified review Free cancellation available CA $813 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/6-hours-healdsburg-wine-tour-with-luxury-suv.a48379179.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Private Sonoma Hidden Gems Redwoods Coast and Artisan Picnic](https://mediaim.expedia.com/localexpert/52066260/1ed5c213-fad5-4212-87da-d96ee256e5ef.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Sonoma Hidden Gems Redwoods Coast and Artisan Picnic 6h Free cancellation available CA $1,353 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-sonoma-hidden-gems-redwoods-coast-and-artisan-picnic.a52066260.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Healdsburg 6 Hour Private Wine Tour Feat. Coppola Winery, holds 4](https://mediaim.expedia.com/localexpert/49623561/c8dc2a36-06cf-4555-b96a-6157e55a085c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Healdsburg 6 Hour Private Wine Tour Feat. Coppola Winery, holds 4 6h Free cancellation available CA $921 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/6-hours-private-wine-tour-in-healdsburg-featuring-coppola-winery.a49623561.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ### Wildlife & nature [See all 3 activities](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=WildlifeNature) ![Safari West Sonoma Adventure Tour](https://mediaim.expedia.com/localexpert/50905278/33e23bec-d47d-4022-a928-15f72ec55614.jpg?impolicy=resizecrop&rw=500&rh=280) ### Safari West Sonoma Adventure Tour 3h Free cancellation available CA $149 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/safari-west-sonoma-adventure-tour.a50905278.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Classic Safari Adventure at Safari West](https://mediaim.expedia.com/localexpert/50754106/dbf846b5-e128-43a2-afe2-f2cbfc91f9d9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Classic Safari Adventure at Safari West 3h Free cancellation available CA $149 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/classic-safari-adventure-at-safari-west.a50754106.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ![Sonoma Horseback-Riding Tour](https://mediaim.expedia.com/localexpert/2262616/51d68087-7bbf-48cb-a35a-08435d77af63.jpg?impolicy=resizecrop&rw=500&rh=280) ### Sonoma Horseback-Riding Tour 1h 30m 10/10 32 Viator reviews Free cancellation available CA $175 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/sonoma-horseback-riding-tour.a2262616.activity-details?&rid=6327443&location=Windsor+Oaks+Vineyards&swp=off) ### Popular places to visit #### Powell's Sweet Shoppe - Windsor Enjoy an outing to Powell's Sweet Shoppe - Windsor during your stay in Windsor. Stroll along the area's riverfront, or simply savor its top-notch restaurants. [](https://expedia.ca/Powells-Sweet-Shoppe-Windsor-Windsor.d553248621532640709.Vacation-Attraction) #### Chalk Hill Estate Vineyard You can enjoy a tasting or tour at Chalk Hill Estate Vineyard during your travels to Healdsburg. Stroll along the area's riverfront, or simply savor its wineries. [](https://expedia.ca/Chalk-Hill-Estate-Vineyard-Healdsburg.d6240787.Vacation-Attraction) #### Dom Whitney Tasting Lounge Enjoy an outing to Dom Whitney Tasting Lounge during your stay in Windsor. Wander the area's riverfront or simply enjoy one of its wineries. [](https://expedia.ca/Dom-Whitney-Tasting-Lounge-Windsor.d553248621532640707.Vacation-Attraction) #### Badger Dog Park After visiting Badger Dog Park, make a plan to see the other sights and activities in Healdsburg. Check out the shops and top-notch restaurants in this walkable area. [](https://expedia.ca/Badger-Dog-Park-Healdsburg.d906162134464167936.Vacation-Attraction) #### Tayman Park Golf Course Enjoy a round of golf in Healdsburg at Tayman Park Golf Course. Amble around this family-friendly area's riverfront and enjoy its wineries. [](https://expedia.ca/Tayman-Park-Golf-Course-Healdsburg.d553248621532640713.Vacation-Attraction) #### Pezzi King Winery You can enjoy a tasting or tour at Pezzi King Winery during your travels to Healdsburg. Amble around this family-friendly area's riverfront and enjoy its wineries. [](https://expedia.ca/Pezzi-King-Winery-Healdsburg.d6324664.Vacation-Attraction) --- ## Best Lodging Options Near Windsor Oaks Vineyards ## Check availability on hotels close to Windsor Oaks Vineyards [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2026-03-09&endDate=2026-03-10)[Mar 9 - Mar 10](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2026-03-09&endDate=2026-03-10) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2026-03-10&endDate=2026-03-11)[Mar 10 - Mar 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2026-03-10&endDate=2026-03-11) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026)[Mar 13 - Mar 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026)[Mar 20 - Mar 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026) ![Stella Campagna - Brand NEW 3 BD, Pool, Spa](https://images.trvl-media.com/lodging/106000000/105210000/105202300/105202242/7641381c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stella Campagna - Brand NEW 3 BD, Pool, Spa Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Brand-NEW-3-BD.h105202242.Hotel-Information) ![Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining](https://images.trvl-media.com/lodging/102000000/101950000/101943500/101943444/w1258h720x0y0-fb7e1543_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Charming-Retreat-Near-Healdsburg-3-BD-Den.h101943444.Hotel-Information) ![Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi](https://images.trvl-media.com/lodging/94000000/93250000/93240700/93240670/1cf7506f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Healdsburg-Modern-Home.h93240670.Hotel-Information) ![Charming house in Healdsburg with Pool and Hot Tub](https://images.trvl-media.com/lodging/114000000/113590000/113586200/113586159/w1194h880x0y0-ba6ecd35_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming house in Healdsburg with Pool and Hot Tub Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Charming-3-Bedroom-House-In-Healdsburg-With-Pool-And-Hot-Tub.h113586159.Hotel-Information) ![Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg](https://images.trvl-media.com/lodging/68000000/67550000/67543500/67543442/94e5f214_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Spectacular-Views.h67543442.Hotel-Information) ![Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball](https://images.trvl-media.com/lodging/100000000/99240000/99231100/99231051/ae2ea03a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-Renovated-Farmhouse-With-Vineyard-Views.h99231051.Hotel-Information) ![Hampton Inn & Suites Windsor - Sonoma Wine Country](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292819/44bef7b5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Windsor - Sonoma Wine Country 8937 Brooks Road South Windsor CA [](https://expedia.ca/Windsor-Hotels-Hampton-Inn-Suites-Windsor-Sonoma-Wine-Country.h2292819.Hotel-Information) ![Holiday Inn Express® Windsor Sonoma Wine Country by IHG](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/6e9c3a9c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express® Windsor Sonoma Wine Country by IHG 8865 Conde Lane Windsor CA [](https://expedia.ca/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.Hotel-Information) ![Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg](https://images.trvl-media.com/lodging/19000000/18770000/18767200/18767186/w1916h1080x0y0-1e0705b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg Healdsburg CA [](https://expedia.ca/Windsor-Hotels-Modern-Farmhouse-2021-Remodel.h18767186.Hotel-Information) [See all 984 properties in Windsor Oaks Vineyards](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6327443) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 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