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) Tours & day trips [](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=ToursDayTrips) Food, drink & nightlife [](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=FoodDrinkNightlife) Adventure & outdoor [](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=AdventureOutdoor) Private & custom tours [](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=Privatecustomtours) Wildlife & nature [](https://expedia.ca/things-to-do/search?&rid=6327443&location=Windsor+Oaks+Vineyards&filter.categories=WildlifeNature) * * * * * * ## Plan a trip to see Windsor Oaks Vineyards Price found within the past 48 hours. Click for updated prices. ![Silverado Resort](https://images.trvl-media.com/lodging/1000000/20000/16500/16466/0ba83454_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Silverado Resort CA $825 per person Nov 14 - Nov 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Oakland (OAK) 8.8/10 Excellent! (1,051 reviews) Outdoor dining/patio was very nice and beautiful views. Clean cottage, front desk staff was very courteous. Housecleaning was thorough and request for extra water was quick. Amenities in cottage missing were paper products like napkins/paper towels, no filtered water or ice. Other wise very nice and quite. Reviewed on Sep 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YEG&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16466&paandie=true&dealMarker=n5HdZvsqH8RXHZEDY1p-0aBX2UtUjvNxvBdpXKrM55vm8mfD8DjbUlq2KLK0uJlD) ![Claremont Resort & Club](https://images.trvl-media.com/lodging/1000000/10000/6700/6609/d997dca7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Claremont Resort & Club Claremont Hills CA $1,299 per person Dec 26 - Dec 31 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Oakland (OAK) 8.8/10 Excellent! (1,014 reviews) The hotel looks beautiful from afar, but actually staying there it feels and looks dated with some obvious room for improvement. The room felt worn with multiple scuffs and dings left and right (on the walls, the furniture, carpeting, etc)...it doesn't feel high quality whatsoever). That being said, the rate we secured was super reasonable ($285/night) day-of on a Thursday, so I was fine with it. I would not have been happy had I paid anything beyond $400, though. Additionally, the prices for food, beverages, spa treatments, etc. are exorbitant and feel like an insane ripoff for what they are. We ordered room service for dinner which had limited options, but was good and nicely portioned (better be for the cost!), but 22% gratuity built in on top of another 10ish% service charge and a delivery fee...you know what you're getting, I guess. Provisions was good, but also overpriced, and feels like a clunky ordering experience. The people working there are SUPER nice and accommodating, but the lines are constant and it feels like it could be more efficient overall. We have also used the pool facilities multiple times and they also feel like they are in dire need of updates. It's amazing to have access to such large, resort-level amenities, but the kids pool and surrounding area felt dirty, the pool chairs look and feel really basic, the staff seem overworked and do not help with getting set up. Again, if I had paid more I would be annoyed. Food for thought! Reviewed on Oct 11, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-31/?FromAirport=YYZ&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6609&paandie=true&dealMarker=Y5EDCh6qEdMd9r92uLY6jAFNAFqyetK5y_OAv6rZ9XPKUWu7kp-N3uxayWyL9mJ4) ![Vino Bello Resort](https://images.trvl-media.com/lodging/2000000/1510000/1509800/1509748/c9623434_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vino Bello Resort Soscol Gateway South CA $915 per person Nov 14 - Nov 18 found 24 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Oakland (OAK) 8.4/10 Very Good! (1,003 reviews) The room was clean and comfortable. Staff was very friendly and helpful. Cameryn one of the Concierge’s was wonderful and assisted us with some great vineyards to visit. The shuttle bus driver Armando was amazing! He was so friendly and helpful he made the ride to and from downtown Napa so much fun. Since our room was part of a vacation club some services you had to call for daily, but was taken care of promptly when asked. Overall Enjoyable stay. Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-18/?FromAirport=YEG&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1509748&paandie=true&dealMarker=n5HdZvsqH8RXHZEDY1p-0aBX2UtUjvNxvBdpXKrM55t5Lgs2geaUR9D8eUQR_kIM) ### 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 wineries. [](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 top-notch restaurants. [](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 top-notch restaurants. [](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 wineries 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 top-notch restaurants. [](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 lively bars. [](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 [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-11&endDate=2025-10-12) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-11&endDate=2025-10-12) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-11&endDate=2025-10-12) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-11&endDate=2025-10-12)[Oct 11 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-11&endDate=2025-10-12) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-12&endDate=2025-10-13) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-12&endDate=2025-10-13) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-12&endDate=2025-10-13) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-12&endDate=2025-10-13)[Oct 12 - Oct 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-10-12&endDate=2025-10-13) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025)[Oct 17 - Oct 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=17%2F10%2F2025&endDate=19%2F10%2F2025) ![Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg](https://images.trvl-media.com/lodging/91000000/90930000/90927800/90927788/b6dff04e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg Healdsburg [](https://expedia.ca/Healdsburg-Hotels-Vineyard-Living-Close-To-Charming-Downtown-Healdsburg.h90927788.Hotel-Information) ### Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining Healdsburg [](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/94000000/93250000/93240700/93240670/7c1ce8de_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi Healdsburg [](https://expedia.ca/Healdsburg-Hotels-Healdsburg-Modern-Limerick.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 [](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/a6b02e37_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg Healdsburg [](https://expedia.ca/Healdsburg-Hotels-Spectacular-Views.h67543442.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) ![Xanadu Healdsburg | Luxury Estate in Healdsburg](https://images.trvl-media.com/lodging/71000000/70560000/70558500/70558491/56b67b48_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Xanadu Healdsburg | Luxury Estate in Healdsburg Healdsburg [](https://expedia.ca/Healdsburg-Hotels-XANADU-HEALDSBURG.h70558491.Hotel-Information) ![Hampton Inn & Suites Windsor - Sonoma Wine Country](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292819/d8f70637_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 Windsor Wine Country by IHG](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/48ef5836_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Windsor Wine Country by IHG 8755 Old Redwood Hwy, Windsor, CA [](https://expedia.ca/Windsor-Hotels-Holiday-Inn-Windsor-Wine-Country.h13235845.Hotel-Information) [See all 995 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. 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[Flights to Healdsburg](https://www.expedia.ca/Cheap-Flights-To-Healdsburg.d8322.Travel-Guide-Flights) - [Flights from Healdsburg](https://www.expedia.ca/lp/flights/8322/flights-from-healdsburg) - [Flights from Windsor](https://www.expedia.ca/lp/flights/9542/flights-from-windsor) - [Armstrong Redwoods State Park](https://www.expedia.ca/Armstrong-Redwoods-State-Park-Guerneville.d6087093.Vacation-Attraction) - [Beaver Creek Vineyards](https://www.expedia.ca/Beaver-Creek-Vineyards-Middletown.d6335693.Vacation-Attraction) - [Bennett Valley Vacations](https://www.expedia.ca/Bennett-Valley.d736344695855443968.Destination-Travel-Guides) - [Bohemian Grove](https://www.expedia.ca/Bohemian-Grove-Sebastopol.d6087095.Vacation-Attraction) - [Calistoga Hot Springs](https://www.expedia.ca/Calistoga-Hot-Springs-Calistoga.d6065815.Vacation-Attraction) - [Calistoga Vacations](https://www.expedia.ca/Calistoga.d6668.Destination-Travel-Guides) - [Castello di Amorosa](https://www.expedia.ca/Castello-Di-Amorosa-Calistoga.d6208243.Vacation-Attraction) - [Charles Krug Winery](https://www.expedia.ca/Charles-Krug-Winery-St-Helena.d6065835.Vacation-Attraction) - [Chateau Montelena Winery](https://www.expedia.ca/Chateau-Montelena-Winery-Calistoga.d6239667.Vacation-Attraction) - [Chateau St. Jean Winery](https://www.expedia.ca/Chateau-St-Jean-Winery-Kenwood.d6128072.Vacation-Attraction) - [Cloverdale Vacations](https://www.expedia.ca/Cloverdale.d177480.Destination-Travel-Guides) - [Dry Creek Vineyard](https://www.expedia.ca/Dry-Creek-Vineyard-Healdsburg.d6240812.Vacation-Attraction) - [Francis Ford Coppola Winery](https://www.expedia.ca/Francis-Ford-Coppola-Winery-Geyserville.d553248621532640800.Vacation-Attraction) - [Jenner Vacations](https://www.expedia.ca/Jenner.d182983.Destination-Travel-Guides) - [Johnson's Beach](https://www.expedia.ca/Johnsons-Beach-Guerneville.d6327098.Vacation-Attraction) - [Ledson Winery and Vineyards](https://www.expedia.ca/Ledson-Winery-And-Vineyards-Kenwood.d6128106.Vacation-Attraction) - [Mazzocco Winery](https://www.expedia.ca/Mazzocco-Winery-Healdsburg.d6324652.Vacation-Attraction) - [Middletown Vacations](https://www.expedia.ca/Middletown.d180934.Destination-Travel-Guides) - [Occidental Vacations](https://www.expedia.ca/Occidental.d500727.Destination-Travel-Guides) - [Old Faithful Geyser of California](https://www.expedia.ca/Old-Faithful-Geyser-Of-California-Calistoga.d6065829.Vacation-Attraction) - [Osmosis Day Spa Sanctuary](https://www.expedia.ca/Osmosis-Day-Spa-Sanctuary-Sebastopol.d553248621532640642.Vacation-Attraction) - [River Rock Casino](https://www.expedia.ca/River-Rock-Casino-Geyserville.d6327089.Vacation-Attraction) - [Santa Rosa Vacations](https://www.expedia.ca/Santa-Rosa.d3288.Destination-Travel-Guides) - [Sharpsteen Museum](https://www.expedia.ca/Sharpsteen-Museum-Calistoga.d6065819.Vacation-Attraction) - [Soda Rock Winery](https://www.expedia.ca/Soda-Rock-Winery-Healdsburg.d6324674.Vacation-Attraction) - [Sonoma Coast State Park](https://www.expedia.ca/Sonoma-Coast-State-Park-California.d6326892.Vacation-Attraction) - [Sonoma County Vacations](https://www.expedia.ca/Sonoma-County.d553248621593965866.Destination-Travel-Guides) - [Spring Lake Park](https://www.expedia.ca/Spring-Lake-Park-Santa-Rosa.d6327420.Vacation-Attraction) - [Villa Grande Vacations](https://www.expedia.ca/Villa-Grande.d3000428920.Destination-Travel-Guides) - [Windsor Vacations](https://www.expedia.ca/Windsor.d9542.Destination-Travel-Guides) - [Visit Windsor](https://www.expedia.ca/Windsor.dx9542) - [Car rental Healdsburg](https://www.expedia.ca/Car-Rentals-In-Healdsburg.d8322.Car-Rental-Guide) - [Car rental Windsor](https://www.expedia.ca/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide) - [Car rentals in Thrifty Car Rental 100 World Parkway](https://www.expedia.ca/Thrifty-Car-Rental-at-100-World-Parkway-St-Johns-Newfoundland-And-Labrador-CAN.v9542.Car-Rental-Guide-Location) - [Things to do in Windsor](https://www.expedia.ca/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)