Title: TOP Winery Hotels in Southside, VA for 2026 | Expedia.co.uk [Southside Travel Guide](https://expedia.co.uk/Southside.dx6346599)[Hotels in Southside](https://expedia.co.uk/Southside-Hotels.d6346599.Travel-Guide-Hotels)[Holiday Rentals in Southside](https://expedia.co.uk/Southside-Holiday-Rentals.d6346599.Travel-Guide-HolidayRentals)[Flights to Southside](https://expedia.co.uk/Cheap-Flights-To-Southside.d6346599.Travel-Guide-Flights)[Southside Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Southside.d6346599.Car-Hire-Guide)[Southside Holidays](https://expedia.co.uk/Southside.d6346599.Holidays-City-Breaks) ![Aerial photograph of Virginia International Raceway or VIR.](https://images.trvl-media.com/place/6346599/1a7d6112-1df3-4340-a1b1-00995ece53a1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6346599/1a7d6112-1df3-4340-a1b1-00995ece53a1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [6 Mar - 7 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6346599&startDate=2026-03-06&endDate=2026-03-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [7 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6346599&startDate=2026-03-07&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6346599&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6346599&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Southside hotels with winery ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/589ca81e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top 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) ![Standard Studio Suite, 1 King Bed with Sofa bed, Accessible, Bathtub | Premium bedding, pillow-top beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/b1964227.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/d34d32a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Richmond/Arboretum [](https://www.expedia.co.uk/Richmond-Hotels-Hyatt-Place-RichmondArboretum.h40501.Hotel-Information) North Chesterfield 8.0/10 Very good (1,005 reviews) "Check in very warm & personalble. Room clean & amenities excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline £95 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Richmond-Hotels-Hyatt-Place-RichmondArboretum.h40501.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/723d4e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/534f78c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/44682183.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking, Jetted Tub | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/9dceed58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Richmond-North Chesterfield [](https://www.expedia.co.uk/Richmond-Hotels-Econo-Lodge.h12133.Hotel-Information) Midlothian 6.2/10 (759 reviews) "The people were super nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gerald £81 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Richmond-Hotels-Econo-Lodge.h12133.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/5bf87aa9.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) ![Dining](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/f7c667b7.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 [](https://www.expedia.co.uk/Richmond-Hotels-The-Virginia-Cliffe-Inn.h34505697.Hotel-Information) Glen Allen 9.6/10 Exceptional (123 reviews) "Room was exactly as described. Super clean and wonderful amenities. Breakfast was OUTSTANDING. Can't wait to come back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven [](https://www.expedia.co.uk/Richmond-Hotels-The-Virginia-Cliffe-Inn.h34505697.Hotel-Information) ![Room, 1 Queen Bed | Living area | 45-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/7d875989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily cooked-to-order breakfast ](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/91623595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed | Individually decorated, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/0dfaf3d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Ragland Mansion Bed & Breakfast [](https://www.expedia.co.uk/Petersburg-Hotels-Ragland-Mansion-Bed-Breakfast.h18087365.Hotel-Information) Petersburg 9.8/10 Exceptional (367 reviews) "Everything was great! The room was spacious and clean, the amenities exceeded expectations and the staff was superb! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kris £126 includes taxes & fees 11 Mar - 12 Mar [](https://www.expedia.co.uk/Petersburg-Hotels-Ragland-Mansion-Bed-Breakfast.h18087365.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/4bcf03c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/5d9f1c91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/7b6d4f7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/abb26aa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations [](https://www.expedia.co.uk/Richmond-Hotels-A-Cozy-And-Classic-Hatteras-43-Yacht-In-One-Of-The-Best-James-River-Locations.h26832035.Hotel-Information) Richmond 9.6/10 Exceptional (114 reviews) "Ron was a generous and gracious host in greeting us and showing us around." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roger C. £161 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Richmond-Hotels-A-Cozy-And-Classic-Hatteras-43-Yacht-In-One-Of-The-Best-James-River-Locations.h26832035.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/19000000/18770000/18763000/18762960/5a59090b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, memory-foam beds, in-room safe, iron/ironing board](https://images.trvl-media.com/lodging/19000000/18770000/18763000/18762960/32cb3b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18770000/18763000/18762960/a4a04667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18763000/18762960/24c2908c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city [](https://www.expedia.co.uk/Richmond-Hotels-A-Warm-And-Cozy-50-Houseboat-In-Gated.h18762960.Hotel-Information) Richmond 9.4/10 Exceptional (229 reviews) "Beautiful setting and comfortable accommodations. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) deirdre b. £161 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Richmond-Hotels-A-Warm-And-Cozy-50-Houseboat-In-Gated.h18762960.Hotel-Information) ![Games room](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/9b8d5fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, free minibar, individually decorated](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/f8b17873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/993484c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Games room](https://images.trvl-media.com/lodging/43000000/42650000/42645600/42645553/f09a5667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A house full of steel balls and games [](https://www.expedia.co.uk/Richmond-Hotels-A-House-Full-Of-Steel-Balls-And-Games.h42645553.Hotel-Information) Dumbarton 9.6/10 Exceptional (107 reviews) "We had a terrific stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hayden £87 includes taxes & fees 23 Mar - 24 Mar [](https://www.expedia.co.uk/Richmond-Hotels-A-House-Full-Of-Steel-Balls-And-Games.h42645553.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/119948bb.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) ![Exterior](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/d45009cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/3623b418.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 [](https://www.expedia.co.uk/New-Kent-Hotels-Cozy-2-Bedroom-Farmhouse-Situated-On-12-Acres-In-New-Kent-County-With-WiFi.h109405997.Hotel-Information) New Kent 10/10 Exceptional (13 reviews) "I hope to stay there again soon." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jim J. £179 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/New-Kent-Hotels-Cozy-2-Bedroom-Farmhouse-Situated-On-12-Acres-In-New-Kent-County-With-WiFi.h109405997.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82810000/82802200/82802155/7d0d6c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/bathtub, hair dryer, towels, soap](https://images.trvl-media.com/lodging/83000000/82810000/82802200/82802155/f78f72fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/83000000/82810000/82802200/82802155/821ce583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/83000000/82810000/82802200/82802155/8c220f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Clean, Quiet, & Cozy Ashland Home [](https://www.expedia.co.uk/Richmond-Hotels-Cozy-3-Bedroom-Close-To-College.h82802155.Hotel-Information) Ashland 9.6/10 Exceptional (51 reviews) "The property was cozy and the host was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daren Z. £254 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Richmond-Hotels-Cozy-3-Bedroom-Close-To-College.h82802155.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.co.uk/Hotel-Search?startDate=2026-03-20&endDate=2026-03-21®ionId=6346599&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_SPRING_PROMO_6346599) ## Top Southside Hotel Reviews ![The Commonwealth](https://images.trvl-media.com/lodging/1000000/40000/39900/39891/e7d64633_y.jpg) ### The Commonwealth 10/10 Excellent "Great stay and easy check in " [](https://expedia.co.uk/Richmond-Hotels-The-Commonwealth.h39891.Hotel-Information) ![Motel 6 Sandston, VA - Richmond, Va](https://images.trvl-media.com/lodging/1000000/1000000/996400/996383/ccd8dad9_y.jpg) ### Motel 6 Sandston, VA - Richmond, Va 6/10 Okay "The people are nice rooms are clean internet not so good but overall its a good place to sleep" [](https://expedia.co.uk/Richmond-Hotels-Motel-6-Sandston.h996383.Hotel-Information) ![The Berkeley Hotel](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/c31357d0_y.jpg) ### The Berkeley Hotel 10/10 Excellent "It stated there was breakfast but it was closed" [](https://expedia.co.uk/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) ![Regency Inn Richmond](https://images.trvl-media.com/lodging/1000000/20000/13900/13851/06fd69a0_y.jpg) ### Regency Inn Richmond 6/10 Okay "Staff were accommodating. Bathroom looks outdated with paints peeling off. WiFi was slow. Probably can use an upgrade with the TV or at least get cable on it. Room looked clean but there were stains on the carpet. Pretty much just a room to sleep in. " [](https://expedia.co.uk/Richmond-Hotels-Regency-Inn-Richmond.h13851.Hotel-Information) ![The Jefferson Hotel](https://images.trvl-media.com/lodging/10000000/9870000/9868600/9868548/c8b04136_y.jpg) ### The Jefferson Hotel 10/10 Excellent "Great experience during Christmas time. The hotel was decorated beautifully. Highly suggest making reservations in advance. The room was amazing, loved the tv in the bathroom. The mattress was not comfortable at all, my husband almost resorted to the floor but ended up turning horizontal across the bottom of the bed and it was slightly better. We will definitely return but maybe with a mattress topper! " [](https://expedia.co.uk/Richmond-Hotels-The-Jefferson-Hotel.h9868548.Hotel-Information) ![Best Western PLUS Executive Hotel](https://images.trvl-media.com/lodging/1000000/60000/58700/58682/7d3c2073_y.jpg) ### Best Western PLUS Executive Hotel 2/10 Terrible "Breakfast its literally frozen eggs in a biscuit with coffee… and their staff isn’t help full at all" [](https://expedia.co.uk/Richmond-Hotels-Best-Western-Executive-Hotel.h58682.Hotel-Information) ![Omni Richmond Hotel](https://images.trvl-media.com/lodging/1000000/20000/13900/13817/7575839d_y.jpg) ### Omni Richmond Hotel 10/10 Excellent "The pool was not available and the room was not vacuumed. " [](https://expedia.co.uk/Richmond-Hotels-Omni-Richmond-Hotel.h13817.Hotel-Information) ![Best Western Premier Richmond City Gateway](https://images.trvl-media.com/lodging/1000000/20000/10300/10271/f67f4a79_y.jpg) ### Best Western Premier Richmond City Gateway 8/10 Good "The bathroom mirror light was not working so was pretty dark in the bathroom. Other than that, everything else was great. Clean and friendly environment. " [](https://expedia.co.uk/Richmond-Hotels-Best-Western-Premier-Richmond-City-Gateway.h10271.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [5 Star Hotels in Bon Air ](https://www.expedia.co.uk/5Star-Bon-Air-Richmond-Hotels.s50-n3000459823-0.Travel-Guide-Filter-Hotels) - [Hotels near Altria Theater ](https://www.expedia.co.uk/Altria-Theater-Hotels.0-l6083633-0.Travel-Guide-Filter-Hotels) - [Hotels near American Civil War Center at Historic Tredegar ](https://www.expedia.co.uk/American-Civil-War-Center-At-Historic-Tredegar-Hotels.0-l6083607-0.Travel-Guide-Filter-Hotels) - [Bon Air Hotels ](https://www.expedia.co.uk/Bon-Air-Richmond-Hotels.0-n3000459823-0.Travel-Guide-Filter-Hotels) - [British Camp Farms Hotels ](https://www.expedia.co.uk/British-Camp-Farms-Richmond-Hotels.0-n782537819992031232-0.Travel-Guide-Filter-Hotels) - [Byrd Park Hotels ](https://www.expedia.co.uk/Byrd-Park-Richmond-Hotels.0-n782537857143689216-0.Travel-Guide-Filter-Hotels) - 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