Title: Book the Best Lakeside WINERY Hotels in 2026 | Expedia.ca [Hotels in Lakeside](https://expedia.ca/Lakeside-Hotels.d177691.Travel-Guide-Hotels)[Vacation Rentals in Lakeside](https://expedia.ca/Lakeside-Vacation-Rentals.d177691.Travel-Guide-VacationRentals)[Flights to Lakeside](https://expedia.ca/Cheap-Flights-To-Lakeside.d177691.Travel-Guide-Flights)[Lakeside Car Rentals](https://expedia.ca/Car-Rentals-In-Lakeside.d177691.Car-Rental-Guide)[Lakeside Vacation Packages](https://expedia.ca/Lakeside.d177691.Destination-Travel-Guides) ![Lake Jennings ](https://images.trvl-media.com/place/177691/f4ed5ea8-5472-4377-a132-8a3ca236c433.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jmalvarez # Find Winery Hotels in Lakeside, CA from CA $97 - ![](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 Lakeside Winery Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=177691&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=177691&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=177691&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=177691&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Lakeside hotels with winery ![Outdoor pool](https://images.trvl-media.com/lodging/101000000/100230000/100220300/100220213/2985a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/101000000/100230000/100220300/100220213/w508h683x258y0-ff88c3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/101000000/100230000/100220300/100220213/w506h683x259y0-c6272671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/101000000/100230000/100220300/100220213/w506h683x260y0-4c757d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Outside Inn at The Tipsy Goat Ranch [](https://www.expedia.ca/Lakeside-Hotels-The-Outside-Inn-At-The-Tipsy-Goat-Ranch.h100220213.Hotel-Information) Lakeside 10/10 Exceptional (14) "We loved the location and animals!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jackie R. CA $240 CA $410 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lakeside-Hotels-The-Outside-Inn-At-The-Tipsy-Goat-Ranch.h100220213.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101570000/101565500/101565470/05931e69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101570000/101565500/101565470/ac783379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/102000000/101570000/101565500/101565470/7ea36cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/102000000/101570000/101565500/101565470/f6ffcb38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Casita on Surf Ranch is centrally located. to all San Diego attractions [](https://www.expedia.ca/Lakeside-Hotels-The-Morey-De-Prieto-Surf-Ranch-Is-Centrally-Located-To-Everything-In-San-Diego.h101565470.Hotel-Information) Lakeside 9.6/10 Exceptional (5) "This place is so perfect. Stayed for my sons Wedding in Alpine. It has everything you need. The beds are grrat !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin S. CA $178 CA $399 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lakeside-Hotels-The-Morey-De-Prieto-Surf-Ranch-Is-Centrally-Located-To-Everything-In-San-Diego.h101565470.Hotel-Information) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109150000/109142000/109141996/29e2c840.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/110000000/109150000/109142000/109141996/a91a02be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109150000/109142000/109141996/8458565e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Television](https://images.trvl-media.com/lodging/110000000/109150000/109142000/109141996/baf539b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Escondido Lodge [](https://www.expedia.ca/Escondido-Hotels-Escondido-Lodge.h109141996.Hotel-Information) Kit Carson 8.0/10 Very good (252) "Room was clean, a very quiet location. Friendly front desk staff. Thank you for a great nights rest!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassandra CA $88 CA $97 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Escondido-Hotels-Escondido-Lodge.h109141996.Hotel-Information) ![Down comforters, Select Comfort beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/28100/28057/6cfcb2a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/1000000/30000/28100/28057/f7acfdd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/28100/28057/18f756d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/30000/28100/28057/5b570276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham San Diego Poway Miramar [](https://www.expedia.ca/Poway-Hotels-Ramada-By-Wyndham-Poway.h28057.Hotel-Information) Poway 7.0/10 Good (949) "Nice hotel with the great service." ![China](https://a.travel-assets.com/egds/marks/flags/cn.svg) Xiaodong CA $101 CA $111 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Poway-Hotels-Ramada-By-Wyndham-Poway.h28057.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/49000000/48230000/48225200/48225149/b7e6ee26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/49000000/48230000/48225200/48225149/50df5900.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Studio Suite, 1 King Bed, Lake View](https://images.trvl-media.com/lodging/49000000/48230000/48225200/48225149/7578a077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/49000000/48230000/48225200/48225149/ad3d4862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet Mind Mountain Lodge, Retreat and Spa [](https://www.expedia.ca/Julian-Hotels-Quiet-Mind-Mountain-Lodge-Retreat.h48225149.Hotel-Information) Julian 9.2/10 Wonderful (568) "Great views, and quite with peace." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Javier CA $342 CA $370 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Julian-Hotels-Quiet-Mind-Mountain-Lodge-Retreat.h48225149.Hotel-Information) ![5 outdoor pools, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3800/3731/d0f041ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/3800/3731/bc1e5add.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Californian cuisine](https://images.trvl-media.com/lodging/1000000/10000/3800/3731/7fe47de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (Bayside Bungalow Bay) | Living area](https://images.trvl-media.com/lodging/1000000/10000/3800/3731/2fecbf54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise Point Resort & Spa [](https://www.expedia.ca/San-Diego-Hotels-Paradise-Point-Resort-Spa.h3731.Hotel-Information) Mission Bay 8.6/10 Excellent (2350) "Great stay, top tier service and excellent customer care " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Meriem CA $178 CA $278 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/San-Diego-Hotels-Paradise-Point-Resort-Spa.h3731.Hotel-Information) ![1 bedroom, in-room safe, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941624/bd47d65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941624/22ae1d01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941624/4b49246b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, shampoo, toilet paper](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941624/3587b2b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy and Quiet Tiny House Cottage with Skylight 2 Minutes from Main Street [](https://www.expedia.ca/Julian-Hotels-Cozy-And-Quiet-Tiny-House-Cottage-With-Skylight-2-Minutes-From-Main-Street.h104941624.Hotel-Information) Julian 9.6/10 Exceptional (15) "The place was super cute and the host was very helpful. Thanks for a great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mackenzie B. CA $143 CA $239 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Julian-Hotels-Cozy-And-Quiet-Tiny-House-Cottage-With-Skylight-2-Minutes-From-Main-Street.h104941624.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21135/5c5f8e88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/30000/21200/21135/89defadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/30000/21200/21135/844fcbc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Bay View (Balcony)](https://images.trvl-media.com/lodging/1000000/30000/21200/21135/c18834b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin San Diego Gaslamp Quarter [](https://www.expedia.ca/San-Diego-Hotels-The-Westin-San-Diego-Gaslamp-Quarter.h21135.Hotel-Information) Downtown San Diego 8.8/10 Excellent (1001) "Check-in staff was excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin CA $199 CA $270 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/San-Diego-Hotels-The-Westin-San-Diego-Gaslamp-Quarter.h21135.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/95000000/94660000/94650200/94650140/4e340d38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/95000000/94660000/94650200/94650140/da63ca6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/95000000/94660000/94650200/94650140/4e68790a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/95000000/94660000/94650200/94650140/c57a03a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Orchard Hill [](https://www.expedia.ca/Julian-Hotels-Orchard-Hill-Country-Inn.h94650140.Hotel-Information) Julian 9.8/10 Exceptional (270) "Enjoyed our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $318 CA $389 total includes taxes & fees Jan 10 - Jan 11, 2026 [](https://www.expedia.ca/Julian-Hotels-Orchard-Hill-Country-Inn.h94650140.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/65000000/64150000/64146000/64145952/7708c59c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/65000000/64150000/64146000/64145952/26c2c993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/65000000/64150000/64146000/64145952/b686bef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/65000000/64150000/64146000/64145952/c8352cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oak Hill Inn, a cozy botique hotel only a 5min stroll to the heart of Julian!! [](https://www.expedia.ca/Julian-Hotels-Stay-In-The-Julian-Historic-District-And-Enjoy-A-Short-Walk-To-Town-Room-1.h64145952.Hotel-Information) Julian 9.8/10 Exceptional (82) "Oak Hill Inn is a great place to get away from the stress of the city and just chill. Very cozy and sweet patio area as well - loved being visited by chickens a couple times a day as well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin J. CA $138 CA $207 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Julian-Hotels-Stay-In-The-Julian-Historic-District-And-Enjoy-A-Short-Walk-To-Town-Room-1.h64145952.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. 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