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. ![Homewood Suites by Hilton Oakland-Waterfront](https://images.trvl-media.com/lodging/1000000/810000/804400/804389/fc341484_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites by Hilton Oakland-Waterfront East Peralta CA $867 per person Feb 8 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 7.8/10 Good! (664 reviews) The room was OK at best. Furniture was very dated. Laminate was coming off in the kitchen no central air portable air conditioner that worked OK friendly but I wouldn’t recommend staying there. Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-08/2026-02-15/?FromAirport=YTO&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=804389&paandie=true&dealMarker=BjuBhyYUjU1VyUSbXqWn6V5x2sGHSgIxrbrIOz52V7Sq7axSxPYN89FfhtaVln1c) ![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 $1,678 per person Dec 26 - Dec 31 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Oakland (OAK) 8.8/10 Excellent! (1,003 reviews) The view from this hotel is great. The amenities is fantastic they have gray gym pool tennis court lots of parking. It's very close to downtown Berkeley and you can take public transportation to downtown SF fairly easily, lots for dinning options and hiking options. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-31/?FromAirport=YUL&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6609&paandie=true&dealMarker=uFYi4Web8E_xB1SizqkjRWUAJj5GfQuhRcIONjLgj8qiuBGF1Qqrn0bnu2asPcgb) ![Holiday Inn Express Hotel & Suites Oakland-Airport by IHG](https://images.trvl-media.com/lodging/1000000/290000/281600/281599/757bfaf5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Hotel & Suites Oakland-Airport by IHG Airport District CA $1,205 per person Feb 8 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Oakland (OAK) 8.8/10 Excellent! (1,001 reviews) Super Clean, Nice, Great Pancakes, 24/7 Free Coffee.☕️ Reviewed on Nov 24, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-08/2026-02-15/?FromAirport=YTO&Destination=OAK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=281599&paandie=true&dealMarker=2-Bpr9Qq3JrrUwC3RgLnmHWdCMNBFiK_hUJlg9-sRi4mwG6B_OdunqSk88EJGln6) ### 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 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 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=2025-11-26&endDate=2025-11-27) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-26&endDate=2025-11-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-26&endDate=2025-11-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-26&endDate=2025-11-27)[Nov 26 - Nov 27](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-26&endDate=2025-11-27) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-27&endDate=2025-11-28) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-27&endDate=2025-11-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-27&endDate=2025-11-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-27&endDate=2025-11-28)[Nov 27 - Nov 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=2025-11-27&endDate=2025-11-28) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025)[Nov 28 - Nov 30](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=28%2F11%2F2025&endDate=30%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=05%2F12%2F2025&endDate=07%2F12%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=05%2F12%2F2025&endDate=07%2F12%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=05%2F12%2F2025&endDate=07%2F12%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=05%2F12%2F2025&endDate=07%2F12%2F2025)[Dec 5 - Dec 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=6327443&startDate=05%2F12%2F2025&endDate=07%2F12%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 CA [](https://expedia.ca/Healdsburg-Hotels-Vineyard-Living-Close-To-Charming-Downtown-Healdsburg.h90927788.Hotel-Information) ![Charming Retreat near Healdsburg – 3 BD + Den, Outdoor Dining](https://images.trvl-media.com/lodging/102000000/101950000/101943500/101943444/1f4e16a2_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) ![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/a6b02e37_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) ![Xanadu Healdsburg | A Wine Country Escape](https://images.trvl-media.com/lodging/71000000/70560000/70558500/70558491/56b67b48_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Xanadu Healdsburg | A Wine Country Escape Healdsburg CA [](https://expedia.ca/Healdsburg-Hotels-XANADU-HEALDSBURG.h70558491.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) ![Renovated farmhouse with vineyard views, bocce ball court, Ping-Pong, basketball](https://images.trvl-media.com/lodging/100000000/99240000/99231100/99231051/74984cae_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) ![Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg](https://images.trvl-media.com/lodging/19000000/18770000/18767200/18767186/5a4f30ee_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) ![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 965 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/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_6327443) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [4 Star Hotels in Chalk Hill](https://www.expedia.ca/4Star-Chalk-Hill-Hotels.s40-0-d736342871657291776.Travel-Guide-Filter-Hotels) - [Aparthotels in Healdsburg](https://www.expedia.ca/Healdsburg-Apart-Hotels.d8322-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Healdsburg](https://www.expedia.ca/Healdsburg-Bed-And-Breakfast.d8322-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Healdsburg](https://www.expedia.ca/Healdsburg-Guest-Houses.d8322-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Boutique-Hotel.0-0-d8322-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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[Safari Tentalow in Windsor](https://www.expedia.ca/Windsor-Safari-Tentalow.d9542-aaSafariTentalow.Travel-Guide-Accommodation) - [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)