Title: Book the Best Southside WINERY Hotels in 2026 | 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) ![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__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 [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6346599&startDate=2026-02-13&endDate=2026-02-15&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) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/d34d32a3.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) ![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 [](https://www.expedia.ca/Richmond-Hotels-Hyatt-Place-RichmondArboretum.h40501.Hotel-Information) North Chesterfield 8.0/10 Very good (1,002 reviews) "Check in very warm & personalble. Room clean & amenities excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $150 CA $175 total includes taxes & fees Feb 16 - Feb 17 [](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/w1284h945x0y1-aa5388bf.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/f947137f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/18a32796.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/3e6967a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom suite with WiFi and AC in Bon Air [](https://www.expedia.ca/Richmond-Hotels-Charming-1-Bedroom-Suite-With-WiFi-And-AC-In-Bon-Air.h111249510.Hotel-Information) Bon Air 10/10 Exceptional (8 reviews) "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 $134 CA $402 total includes taxes & fees Feb 23 - Feb 24 [](https://www.expedia.ca/Richmond-Hotels-Charming-1-Bedroom-Suite-With-WiFi-And-AC-In-Bon-Air.h111249510.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12200/12133/353363bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Richmond-North Chesterfield [](https://www.expedia.ca/Richmond-Hotels-Econo-Lodge.h12133.Hotel-Information) Midlothian 6.2/10 (759 reviews) "." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristian CA $127 CA $147 total includes taxes & fees Mar 9 - Mar 10 [](https://www.expedia.ca/Richmond-Hotels-Econo-Lodge.h12133.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) ![Marina](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/f45fc0a3.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) ![Dining](https://images.trvl-media.com/lodging/27000000/26840000/26832100/26832035/5d9f1c91.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.ca/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) "2nd time staying at this property and definitely won’t be the last! Amazing location and great host." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis S. CA $157 CA $295 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Richmond-Hotels-A-Cozy-And-Classic-Hatteras-43-Yacht-In-One-Of-The-Best-James-River-Locations.h26832035.Hotel-Information) ![Room, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/19000000/18090000/18087400/18087365/7d875989.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) ![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) ### Ragland Mansion Bed & Breakfast [](https://www.expedia.ca/Petersburg-Hotels-Ragland-Mansion-Bed-Breakfast.h18087365.Hotel-Information) Petersburg 9.8/10 Exceptional (364 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 CA $171 CA $230 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Petersburg-Hotels-Ragland-Mansion-Bed-Breakfast.h18087365.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) ![Interior](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/142d15a7.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) ### The Virginia Cliffe Inn [](https://www.expedia.ca/Richmond-Hotels-The-Virginia-Cliffe-Inn.h34505697.Hotel-Information) Glen Allen 9.6/10 Exceptional (122 reviews) "Wonderful charm to the property and grounds. Owner was very friendly and accommodating. We definitely would stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan [](https://www.expedia.ca/Richmond-Hotels-The-Virginia-Cliffe-Inn.h34505697.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) ![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18763000/18762960/07c0913e.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.ca/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. CA $157 CA $295 total includes taxes & fees Feb 11 - Feb 12 [](https://www.expedia.ca/Richmond-Hotels-A-Warm-And-Cozy-50-Houseboat-In-Gated.h18762960.Hotel-Information) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/c31357d0.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) ![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) ![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 [](https://www.expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) Downtown Richmond 8.8/10 Excellent (1,531 reviews) "We had a very nice stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David [](https://www.expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/470000/460400/460312/f1ffebc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/470000/460400/460312/d6b8468e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/470000/460400/460312/49c456e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/470000/460400/460312/6548da5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn Richmond North [](https://www.expedia.ca/Richmond-Hotels-Sleep-Inn-Richmond-North.h460312.Hotel-Information) Richmond 7.8/10 Good (784 reviews) "Room was very clean, Front Desk Agents was very nice and Food & Stores was very convenient. Highly Recomend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele CA $95 CA $111 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Richmond-Hotels-Sleep-Inn-Richmond-North.h460312.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) ![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 [](https://www.expedia.ca/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. CA $172 CA $328 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/New-Kent-Hotels-Cozy-2-Bedroom-Farmhouse-Situated-On-12-Acres-In-New-Kent-County-With-WiFi.h109405997.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=2026-02-20&endDate=2026-02-21®ionId=6346599&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Southside Hotel Reviews ![Linden Row Inn](https://images.trvl-media.com/lodging/1000000/20000/14100/14059/9f1e05a8_y.jpg) ### Linden Row Inn 10/10 Excellent "Had a great stay! Perfect location for getting around Richmond. Loved seeing Annabelle the hotel cat!" [](https://expedia.ca/Richmond-Hotels-Linden-Row-Inn.h14059.Hotel-Information) ![The Jefferson Hotel](https://images.trvl-media.com/lodging/10000000/9870000/9868600/9868548/c8b04136_y.jpg) ### The Jefferson Hotel 10/10 Excellent "Standouts were the staff, Chas my concierge greeted us at the door, handled our bags, placed them in the room, got us ice, and made sure our needs were met, Ketunde the receptionist was in training, yet she was exceptionally professional and welcoming, easy conversation making us feel at home, the host, and our waiters at the lounge were also very welcoming, and friendly with excellent service and attentiveness, the valets were really sweet, opened doors, made sure the car was nice and toasty when we got inside. Our Queen suite with two Queen beds, a huge bathrooom complete with a luxurious tub, separate huge closet and working area with desk and chair was beyond our expectations. Historic elegance meets modern comforts. You can’t go wrong staying at the Jefferson if you would like to be spoiled and pampered." [](https://expedia.ca/Richmond-Hotels-The-Jefferson-Hotel.h9868548.Hotel-Information) ![Omni Richmond Hotel](https://images.trvl-media.com/lodging/1000000/20000/13900/13817/16c7de39_y.jpg) ### Omni Richmond Hotel 10/10 Excellent "The courteous and smiling" [](https://expedia.ca/Richmond-Hotels-Omni-Richmond-Hotel.h13817.Hotel-Information) ![The Berkeley Hotel](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/2c75da2c_y.jpg) ### The Berkeley Hotel 10/10 Excellent "Renovated room ... modern touches (old rooms were nice too). Very nice room" [](https://expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) ![Regency Inn Richmond](https://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) ![The Commonwealth](https://images.trvl-media.com/lodging/1000000/40000/39900/39891/901fb2f8_y.jpg) ### The Commonwealth 10/10 Excellent "Everyone is friendly and helpful. We LOVED Kinesha (valet)! " [](https://expedia.ca/Richmond-Hotels-The-Commonwealth.h39891.Hotel-Information) ![Comfort Suites At Virginia Center Commons](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916044/1baddeab_y.jpg) ### Comfort Suites At Virginia Center Commons 10/10 Excellent "Staff and size suite. The bottom of the shower was very dirty (stained) but it can be cleaned with a magic eraser" [](https://expedia.ca/Richmond-Hotels-Comfort-Suites-At-Virginia-Center-Commons.h1916044.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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