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 [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2025-11-14&endDate=2025-11-16&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 (1008) "Clean room and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis CA $154 CA $179 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/w1284h945x0y1-aa5388bf.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) ![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) ### Charming 1-bedroom suite with WiFi and AC in Bon Air Bon Air 10/10 Exceptional (7) "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 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica H. CA $149 CA $296 total includes taxes & fees Nov 4 - Nov 5 [](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) ![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) ![Dining](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/78950bf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/121000000/120830000/120825800/120825797/4e2768ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Professional & Functional Modern Stay Near Hospitals,Sky Lounge + Outdoor Pool Old Town Manchester CA $74 CA $414 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) "Nice and clean and affordable. Exactly what I needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $130 CA $151 total includes taxes & fees Dec 1 - Dec 2 [](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/35000000/34510000/34505700/34505697/142d15a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/69349ec9.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) ### The Virginia Cliffe Inn Glen Allen 9.6/10 Exceptional (118) "This was a wonderful bed and breakfast. We enjoyed everything about it!! 😌" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christi [](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) ![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/aa70ef79.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) ![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) ### Ragland Mansion Bed & Breakfast Petersburg 9.8/10 Exceptional (358) "Historical home with meticulously restored architectural detail, beautifully furnished, and a gracious and helpful host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $168 CA $226 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/696aa5c7.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) ![Game room](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/9b8d5fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A house full of steel balls and games Dumbarton 9.6/10 Exceptional (98) "Great place to stay. Pete is a great host, easy check in great communication, pinball machines and games in the rooms really great. Quick drive to some good dining." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $100 CA $134 total includes taxes & fees Nov 16 - Nov 17 [](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) ![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) ![TV](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/e5731aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113120000/113113200/113113175/1698f34f.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 (6) CA $163 CA $206 total includes taxes & fees Nov 13 - Nov 14 [](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) ![Microwave, cookware/dishes/utensils, paper towels, dining tables](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/044f3e2e.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) ![Interior](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/e6f91417.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 (11) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy I. CA $177 CA $333 total includes taxes & fees Nov 3 - Nov 4 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/1d038227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkeley Hotel Downtown Richmond 8.8/10 Excellent (1518) "Good location. Great place. Staff very helpful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STEVE [](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=2025-11-15&endDate=2025-11-16®ionId=6346599&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southside Hotel Reviews ![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 helpful and friendly! Comfortable beds. Good food. Everything was clean and tidy. Would definitely stay again!" [](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 "Agent at the check-in desk was very helpful and patient with me. I really appreciated her professionalism " [](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 "Wonderful two nights! The Jefferson has great food, wonderful accommodations, and an interested staff. We always enjoy our time with the Jefferson " [](https://expedia.ca/Richmond-Hotels-The-Jefferson-Hotel.h9868548.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 the staff at the front desk was very responsive." [](https://expedia.ca/Richmond-Hotels-Hyatt-Place-Richmond-Airport.h2385332.Hotel-Information) ![Regency Inn Richmond](//images.trvl-media.com/lodging/1000000/20000/13900/13851/d4110985_y.jpg) ### Regency Inn Richmond 10/10 Excellent "Yes " [](https://expedia.ca/Richmond-Hotels-Regency-Inn-Richmond.h13851.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 "We had to leave early and did not try breakfast - our room wasn't ready and we got upgraded - the lady at the front desk was very helpful, and the upgrade still fit our needs perfectly. We were happy with our stay, and may stay again soon. We visited for my husband's surgery at the VA hospital, and we were informed that Choice Hotels offers help to Veterans under these conditions. We intend to check into this for our next stay. " [](https://expedia.ca/Richmond-Hotels-Comfort-Suites-At-Virginia-Center-Commons.h1916044.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 "We did not have breakfast. The room was nice. The bathroom is very tiny. The hotel and room were very clean. Good location. " [](https://expedia.ca/Richmond-Hotels-Quality-Inn-West-End.h15606.Hotel-Information) ![Red Roof Inn Richmond South](//images.trvl-media.com/lodging/1000000/10000/8800/8725/4c39dd2b_y.jpg) ### Red Roof Inn Richmond South 10/10 Excellent "Pretty boy " [](https://expedia.ca/Richmond-Hotels-Red-Roof-Inn-Richmond-South.h8725.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) - 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