Title: Book the Best South San Jose WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in San Jose](https://expedia.ca/San-Jose-Vacation-Rentals.d602703.Travel-Guide-VacationRentals)[Flights to San Jose](https://expedia.ca/Cheap-Flights-To-San-Jose.d602703.Travel-Guide-Flights)[Things to do in San Jose](https://expedia.ca/Things-To-Do-In-San-Jose.d602703.Travel-Guide-Activities)[South San Jose Car Rentals](https://expedia.ca/Car-Rentals-In-South-San-Jose.d6254400.Car-Rental-Guide)[South San Jose Vacations](https://expedia.ca/South-San-Jose.d6254400.Destination-Travel-Guides) ![Silicon valley](https://images.trvl-media.com/place/6254400/52755769-cd52-424c-a733-4e67fc90ab53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in South San Jose, CA from CA $141 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on South San Jose Winery Hotels Tonight [Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=6254400&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 20 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6254400&startDate=2025-12-20&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6254400&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6254400&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for South San Jose hotels with winery ![Surfing/boogie boarding](https://images.trvl-media.com/lodging/2000000/1170000/1168000/1167912/2e682ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Queen Combo](https://images.trvl-media.com/lodging/2000000/1170000/1168000/1167912/4a15fd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1170000/1168000/1167912/3b867ce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1170000/1168000/1167912/97f48072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaway Inn [](https://www.expedia.ca/Santa-Cruz-Hotels-Seaway-Inn.h1167912.Hotel-Information) Westside Santa Cruz 9.2/10 Wonderful (145) "The staff are always friendly and helpful. Our room was very clean and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $142 CA $173 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Santa-Cruz-Hotels-Seaway-Inn.h1167912.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/126600/126572/3820c8a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/126600/126572/bd957e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/126600/126572/2d7f91ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/130000/126600/126572/267f96ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Cupertino [](https://www.expedia.ca/Cupertino-Hotels-Hilton-Garden-Inn-Cupertino.h126572.Hotel-Information) Cupertino 8.8/10 Excellent (1000) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander CA $126 CA $141 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Cupertino-Hotels-Hilton-Garden-Inn-Cupertino.h126572.Hotel-Information) ![Deluxe Cottage, 1 Bedroom, Fireplace, Garden Area (Cottage 11B)](https://images.trvl-media.com/lodging/13000000/12510000/12503600/12503533/7b59df89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Queen Bed (Cottage 1)](https://images.trvl-media.com/lodging/13000000/12510000/12503600/12503533/8c9198b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Cottage, 1 Bedroom, Kitchen, River View (Cottage 3) | Balcony](https://images.trvl-media.com/lodging/13000000/12510000/12503600/12503533/3e8eba07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Studio Suite, Kitchenette, Garden View (Cottage 15)](https://images.trvl-media.com/lodging/13000000/12510000/12503600/12503533/d1d45212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fern River Resort [](https://www.expedia.ca/Santa-Cruz-Hotels-Fern-River-Resort.h12503533.Hotel-Information) Felton 9.2/10 Wonderful (462) "Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Echo CA $116 CA $151 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Santa-Cruz-Hotels-Fern-River-Resort.h12503533.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/34000000/33360000/33354500/33354408/a4ca54a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tapas bar](https://images.trvl-media.com/lodging/34000000/33360000/33354500/33354408/a1194e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33360000/33354500/33354408/1c79dd7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33360000/33354500/33354408/2c4074b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel by Marriott San Jose Santa Clara [](https://www.expedia.ca/Santa-Clara-Hotels-AC-Hotel-By-Marriott-San-Jose-Santa-Clara.h33354408.Hotel-Information) Santa Clara 9.4/10 Exceptional (769) "Breakfast service was so good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) EUNYOUNG CA $169 CA $198 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Santa-Clara-Hotels-AC-Hotel-By-Marriott-San-Jose-Santa-Clara.h33354408.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/30000/23600/23513/dd9c5bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23600/23513/b8e7fcb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/30000/23600/23513/ea9447f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23600/23513/eb59a431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Silicon Valley [](https://www.expedia.ca/Milpitas-Hotels-Sonesta-Silicon-Valley.h23513.Hotel-Information) Milpitas 9.0/10 Wonderful (1642) "Definitely the best hotel I've stayed at so far, i look forward to staying here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ubaldo CA $146 CA $167 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Milpitas-Hotels-Sonesta-Silicon-Valley.h23513.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/30000/27600/27566/9f8bd72a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/30000/27600/27566/7be576e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/27600/27566/50eb0132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/30000/27600/27566/90062000.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chaminade Resort & Spa [](https://www.expedia.ca/Santa-Cruz-Hotels-Chaminade-Resort-Spa.h27566.Hotel-Information) Santa Cruz 8.0/10 Very good (1000) "A pleasant and polite welcome to the hotel by the staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jan CA $185 CA $269 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Santa-Cruz-Hotels-Chaminade-Resort-Spa.h27566.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7320000/7317900/7317889/06f0a3b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7320000/7317900/7317889/2d0daa45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7320000/7317900/7317889/08013122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Cottage - Pet Friendly](https://images.trvl-media.com/lodging/8000000/7320000/7317900/7317889/44560456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Echo Inn and Beach Cottages [](https://www.expedia.ca/Santa-Cruz-Hotels-Ocean-Echo-Inn-And-Beach-Cottages.h7317889.Hotel-Information) Eastside Santa Cruz 8.8/10 Excellent (573) "Super cute, perfect location, and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacki CA $199 CA $229 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Santa-Cruz-Hotels-Ocean-Echo-Inn-And-Beach-Cottages.h7317889.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/810/f2e91177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/900/810/61d6974e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/810/467b803b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/810/w3840h2547x0y0-5d4c41ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Morgan Hill [](https://www.expedia.ca/Morgan-Hill-Hotels-Hampton-Inn-Morgan-Hill.h810.Hotel-Information) Morgan Hill 9.0/10 Wonderful (1004) "Clean, comfortable, courteous staff, hearty breakfast, helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David Ben CA $144 CA $162 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Morgan-Hill-Hotels-Hampton-Inn-Morgan-Hill.h810.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/890000/889800/889769/46d85f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/1000000/890000/889800/889769/61de8a60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/889800/889769/4a59cab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/1000000/890000/889800/889769/5f4ce610.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Saratoga Oaks Lodge [](https://www.expedia.ca/Saratoga-Hotels-Saratoga-Oaks-Lodge.h889769.Hotel-Information) Saratoga 9.4/10 Exceptional (971) "Nice location, clean and comfortable room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $176 CA $194 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Saratoga-Hotels-Saratoga-Oaks-Lodge.h889769.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/24100/24061/w3836h2557x4y3-e4806961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24100/24061/w3837h2557x3y3-05ed0887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/24100/24061/w3837h2557x3y3-e973135f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24100/24061/w3837h2557x3y3-df8023ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton San Jose Airport-Silicon Valley [](https://www.expedia.ca/San-Jose-Hotels-Homewood-Suites-By-Hilton-San-Jose-Airport-Silicon-Valley.h24061.Hotel-Information) North San Jose 8.8/10 Excellent (630) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ricardo CA $154 CA $178 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/San-Jose-Hotels-Homewood-Suites-By-Hilton-San-Jose-Airport-Silicon-Valley.h24061.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-02&endDate=2026-01-03®ionId=6254400&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top South San Jose Hotel Reviews ![Sonesta Select San Jose Airport](https://images.trvl-media.com/lodging/1000000/20000/16900/16897/f3399389_y.jpg) ### Sonesta Select San Jose Airport 10/10 Excellent "It had everything we needed except for a refrigerator and a microwave. Otherwise great place to stay." [](https://expedia.ca/San-Jose-Hotels-Sonesta-Select-San-Jose-Airport.h16897.Hotel-Information) ![Sonesta Silicon Valley](https://images.trvl-media.com/lodging/1000000/30000/23600/23513/df665399_y.jpg) ### Sonesta Silicon Valley 10/10 Excellent "Staff was extremely courteous and helpful. Room was clean and well-kept. " [](https://expedia.ca/Milpitas-Hotels-Sonesta-Silicon-Valley.h23513.Hotel-Information) ![Hotel Paradox, Autograph Collection](https://images.trvl-media.com/lodging/1000000/20000/11100/11056/bbbd3a94_y.jpg) ### Hotel Paradox, Autograph Collection 10/10 Excellent "The room was simple and clean, but honestly the staff were top notch. The man running the front desk when we arrived on 12/14 was quick but very good at dispersing information. He even have me a follow up call to tell me of information her had forgotten to say regarding some morning alarns! And when i decided to get a night cap or two, Kelly the bartender was so calming and fun to talk with even though things were slow he was foused on tasks need to be achieved along with paying attention to the customers. Great job!" [](https://expedia.ca/Santa-Cruz-Hotels-Hotel-Paradox.h11056.Hotel-Information) ![The Westin San Jose](https://images.trvl-media.com/lodging/1000000/10000/9300/9242/a2c02fdc_y.jpg) ### The Westin San Jose 10/10 Excellent "Every one that worked with us was great. The door man to the desk clerk to the gentleman that helped us with our bags. The location was very good for downtown SanJose, a lot of things within walking distance.We would stay here again." [](https://expedia.ca/San-Jose-Hotels-The-Westin-San-Jose.h9242.Hotel-Information) ![Hyatt Centric Santa Clara Silicon Valley](https://images.trvl-media.com/lodging/1000000/30000/25400/25373/28094cb7_y.jpg) ### Hyatt Centric Santa Clara Silicon Valley 10/10 Excellent "Very nice" [](https://expedia.ca/Santa-Clara-Hotels-Hyatt-Centric-Santa-Clara-Silicon-Valley.h25373.Hotel-Information) ![The Domain Hotel](https://images.trvl-media.com/lodging/1000000/30000/21500/21433/2e56a61f_y.jpg) ### The Domain Hotel 10/10 Excellent "very comfortable and clean " [](https://expedia.ca/Sunnyvale-Hotels-The-Domain-Hotel.h21433.Hotel-Information) ![Hotel De Anza ](https://images.trvl-media.com/lodging/1000000/570000/564500/564411/e0e72fc7_y.jpg) ### Hotel De Anza 10/10 Excellent "Cute retro hotel, walking distance to San Pedro Square with every Restaurant you want and bars. Jr suites are a perfect stay with meters in front or you will pay a lot for Valet. Nice staff who made our stay amazing so we stayed another night and went to Christmas in the park. No bar but they said March it’s reopening. Plenty of places to go near by!!" [](https://expedia.ca/San-Jose-Hotels-Hotel-De-Anza.h564411.Hotel-Information) ![Maple Tree Inn](https://images.trvl-media.com/lodging/1000000/20000/13900/13802/4363ca08_y.jpg) ### Maple Tree Inn 10/10 Excellent "Everything was great: clean room, great staff, great location" [](https://expedia.ca/Sunnyvale-Hotels-Maple-Tree-Inn.h13802.Hotel-Information) ![Spark by Hilton San Jose Airport](https://images.trvl-media.com/lodging/1000000/20000/11500/11484/f79ad4e2_y.jpg) ### Spark by Hilton San Jose Airport 10/10 Excellent "Nunca recivi mi deposito de $100 y nadie me.responde en la oficina " [](https://expedia.ca/San-Jose-Hotels-Spark-By-Hilton-San-Jose-Airport.h11484.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Almaden Valley ](https://www.expedia.ca/Almaden-Valley-San-Jose-Hotels-Adults-Only-Resorts.0-n553248635976469220-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Almaden Valley ](https://www.expedia.ca/Almaden-Valley-San-Jose-Hotels-Hotel-With-Early-Check-In.0-n553248635976469220-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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[Luxury Hotels in Evergreen ](https://www.expedia.ca/Evergreen-San-Jose-Hotels-Luxury-Hotel.0-n553248635976472809-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-All-Inclusive-Hotel.0-n800128-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-Beach-Hotel.0-n800128-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-Hotel-With-Early-Check-In.0-n800128-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-Hotel-With-Wifi.0-n800128-0-tHotelwithwifi.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-Hotels-With-Hot-Tubs.0-n800128-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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[Hotel Wedding Venues Hotels in Fisherman's Wharf ](https://www.expedia.ca/Fishermans-Wharf-San-Francisco-Hotels-Wedding-Hotels.0-n800128-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Half Moon Bay ](https://www.expedia.ca/Half-Moon-Bay-Hotels-Hotels-With-Indoor-Pool.0-0-d8250-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Monterey ](https://www.expedia.ca/Monterey-Hotels-Hotels-With-Smoking-Rooms.0-0-d180045-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lake Hotels in Monterey ](https://www.expedia.ca/Monterey-Hotels-Lake-Hotels.0-0-d180045-tLakeHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Monterey ](https://www.expedia.ca/Monterey-Hotels-Wedding-Hotels.0-0-d180045-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Casino Hotels in Nob Hill ](https://www.expedia.ca/Nob-Hill-San-Francisco-Hotels-Casino-Hotel.0-n138629-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Nob Hill ](https://www.expedia.ca/Nob-Hill-San-Francisco-Hotels-LGBT-Friendly-Hotel.0-n138629-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - 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