Title: Book the Best Southside WINERY Hotels in 2025 | Expedia.ca [Southside Travel Guide](https://expedia.ca/Southside.dx6346599)[Hotels in Southside](https://expedia.ca/Southside-Hotels.d6346599.Travel-Guide-Hotels)[Vacation Rentals in Southside](https://expedia.ca/Southside-Vacation-Rentals.d6346599.Travel-Guide-VacationRentals)[Flights to Southside](https://expedia.ca/Cheap-Flights-To-Southside.d6346599.Travel-Guide-Flights)[Southside Car Rentals](https://expedia.ca/Car-Rentals-In-Southside.d6346599.Car-Rental-Guide)[Southside Vacation Packages](https://expedia.ca/Southside.d6346599.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/d89a1369870f94185b3ca50a611dc10a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Southside, VA ![](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 Southside Winery Hotels Tonight [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Southside Winery Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/563e995d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/e5f685c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/03578213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio Suite, 1 King Bed with Sofa bed, Accessible, Bathtub](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/b1964227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Richmond/Arboretum North Chesterfield 7.8/10 Good (1011) "Room was clean staff and bar was nice " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Niyokwizigira CA $155 CA $180 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Richmond-Hotels-Hyatt-Place-RichmondArboretum.h40501.Hotel-Information) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/f947137f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/873a7168_edited_2932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/w1283h1698x0y0-5076d136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/9dd424b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom suite with WiFi and AC in Bon Air Bon Air 10/10 Exceptional (6) "It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica H. CA $149 CA $297 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Richmond-Hotels-Charming-1-Bedroom-Suite-With-WiFi-And-AC-In-Bon-Air.h111249510.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/f608bc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/78950bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/a0765066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/5cb88ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sky Lounge Pool, Chic Luxury Stay in the City Old Town Manchester CA $91 CA $440 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Richmond-Hotels-Sky-Lounge-Pool.h120825797.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/44682183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/67391eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Smoking](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/2386437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/c748764c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Richmond-North Chesterfield Midlothian 6.2/10 (755) "." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristian CA $118 CA $137 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Richmond-Hotels-Econo-Lodge.h12133.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/c75ecfba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/6ee47e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/b42c1d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/142d15a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Virginia Cliffe Inn Glen Allen 9.6/10 Exceptional (117) "Wonderful charm to the property and grounds. Owner was very friendly and accommodating. We definitely would stay again. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $248 CA $283 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Richmond-Hotels-The-Virginia-Cliffe-Inn.h34505697.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/54097e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/0dfaf3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/66adde65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/98388c85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ragland Mansion Bed & Breakfast Petersburg 9.8/10 Exceptional (357) "Historical home with meticulously restored architectural detail, beautifully furnished, and a gracious and helpful host." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $169 CA $226 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Petersburg-Hotels-Ragland-Mansion-Bed-Breakfast.h18087365.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/cf90d53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/9b8d5fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/7788227b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/1d9577a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A house full of steel balls and games Dumbarton 9.6/10 Exceptional (97) "Clean, fun. and very kind and responsive owner. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Marian CA $100 CA $135 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Richmond-Hotels-A-House-Full-Of-Steel-Balls-And-Games.h42645553.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/d50239b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/e5731aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/241b5c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/06eb0e3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2-bedroom home, with lake access, in the Richmond metro area. Quinton 10/10 Exceptional (4) "House was amazing and host was very kind and helpful" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron R. CA $181 CA $226 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Quinton-Hotels-Charming-2-Bedroom-Home.h113113175.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/3623b418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/e6f91417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/dcf14d21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/d40363e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2-bedroom farmhouse on 12 acres in New Kent County just 7 miles off of I64 New Kent 10/10 Exceptional (10) "Charming property in the country. Super comfy for a quick getaway, owners were welcoming and thoughtful about what guests would need. Would definitely stay here again if on the area again. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy I. CA $164 CA $300 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/New-Kent-Hotels-Cozy-2-Bedroom-Farmhouse-Situated-On-12-Acres-In-New-Kent-County-With-WiFi.h109405997.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/2c75da2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/bf308e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/3e23e2f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 King Bed, Terrace, City View](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/ca466d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkeley Hotel Downtown Richmond 8.8/10 Excellent (1526) "The Front desk staff was excellent and friendly." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Milton CA $197 CA $229 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.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=2025-10-31&endDate=2025-11-01®ionId=6346599&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southside Hotel Reviews ![The Berkeley Hotel](//images.trvl-media.com/lodging/1000000/10000/1900/1860/2c75da2c_y.jpg) ### The Berkeley Hotel 10/10 Excellent "The downside is there is no restaurant in the facility. They rely on a restaurant leased separately. The result is no food available on Mondays at all and limited hours when they are open. Normal restaurant hours but not food service hours in a five star hotel " [](https://expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) ![Holiday Inn Hotel and Suites Richmond West End by IHG](//images.trvl-media.com/lodging/1000000/20000/15700/15606/767da3fd_y.jpg) ### Holiday Inn Hotel and Suites Richmond West End by IHG 10/10 Excellent "Clean room very comforting " [](https://expedia.ca/Richmond-Hotels-Quality-Inn-West-End.h15606.Hotel-Information) ![Comfort Suites At Virginia Center Commons](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916044/1baddeab_y.jpg) ### Comfort Suites At Virginia Center Commons 10/10 Excellent "The front desk was friendly and helpful. " [](https://expedia.ca/Richmond-Hotels-Comfort-Suites-At-Virginia-Center-Commons.h1916044.Hotel-Information) ![Hyatt Place Richmond Airport](//images.trvl-media.com/lodging/3000000/2390000/2385400/2385332/58ccc3ab_y.jpg) ### Hyatt Place Richmond Airport 10/10 Excellent "The airport shuttle to the hotel was what was a deciding factor in staying there. When we arrived after midnight the check in was fast, and easy. The room was large, clean and quiet. " [](https://expedia.ca/Richmond-Hotels-Hyatt-Place-Richmond-Airport.h2385332.Hotel-Information) ![Best Western Premier Richmond City Gateway](//images.trvl-media.com/lodging/1000000/20000/10300/10271/826922f7_y.jpg) ### Best Western Premier Richmond City Gateway 10/10 Excellent "Staff was great and parking was a breeze. " [](https://expedia.ca/Richmond-Hotels-Best-Western-Premier-Richmond-City-Gateway.h10271.Hotel-Information) ![Omni Richmond Hotel](//images.trvl-media.com/lodging/1000000/20000/13900/13817/16c7de39_y.jpg) ### Omni Richmond Hotel 10/10 Excellent "I left an important item at the hotel. Ms. Deborah made sure that I got my item. I tried to give her a ministry gift and she declined. I want to say thank you to her and that the Omni should know what an asset that she is. I am forever greatful." [](https://expedia.ca/Richmond-Hotels-Omni-Richmond-Hotel.h13817.Hotel-Information) ![The Jefferson Hotel](//images.trvl-media.com/lodging/10000000/9870000/9868600/9868548/c8b04136_y.jpg) ### The Jefferson Hotel 10/10 Excellent "N/A " [](https://expedia.ca/Richmond-Hotels-The-Jefferson-Hotel.h9868548.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Fawnbrook](https://www.expedia.ca/3Star-Fawnbrook-Richmond-Hotels.s30-n782537948411133952-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Byrd Park](https://www.expedia.ca/5Star-Byrd-Park-Richmond-Hotels.s50-n782537857143689216-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Midlothian](https://www.expedia.ca/5Star-Midlothian-Richmond-Hotels.s50-n782538075341258752-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in South Garden](https://www.expedia.ca/5Star-South-Garden-Richmond-Hotels.s50-n782538187357921280-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Beaufont](https://www.expedia.ca/Beaufont-Richmond-Hotels-Luxury-Hotel.0-n782537789014384640-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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