Title: Book the Best Ashland WINERY Hotels in 2025 | Expedia.ca [Hotels in Ashland](https://expedia.ca/Ashland-Hotels.d6292.Travel-Guide-Hotels)[Vacation Rentals in Ashland](https://expedia.ca/Ashland-Vacation-Rentals.d6292.Travel-Guide-VacationRentals)[Flights to Ashland](https://expedia.ca/Cheap-Flights-To-Ashland.d6292.Travel-Guide-Flights)[Ashland Car Rentals](https://expedia.ca/Car-Rentals-In-Ashland.d6292.Car-Rental-Guide)[Ashland Vacation Packages](https://expedia.ca/Ashland.d6292.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/c81f35a63666c25ba6ca310aede6cda7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Ashland, VA from CA $134 ![](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 Ashland Winery Hotels Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6292&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6292&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6292&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6292&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Ashland Winery Hotels ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/83000000/82810000/82802200/82802155/0d393e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/tub, 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) ### Clean, Quiet, & Cozy Ashland Home Ashland 9.6/10 Exceptional (48) "The property was cozy and the host was great! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daren Z. CA $232 CA $501 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Richmond-Hotels-Cozy-3-Bedroom-Close-To-College.h82802155.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) ![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) ![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) ![Smart TV](https://images.trvl-media.com/lodging/110000000/109410000/109406000/109405997/dcf14d21.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 $176 CA $333 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/1900/1860/1d038227.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 (1517) "The Front desk staff was excellent and friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Milton CA $195 CA $227 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.Hotel-Information) ![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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/40600/40501/41ec7767.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) ![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) ### Hyatt Place Richmond/Arboretum North Chesterfield 7.8/10 Good (1007) "Clean room and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis CA $153 CA $178 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Richmond-Hotels-Hyatt-Place-RichmondArboretum.h40501.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) ![Miscellaneous](https://images.trvl-media.com/lodging/35000000/34510000/34505700/34505697/69349ec9.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/35000000/34510000/34505700/34505697/6ee47e02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Virginia Cliffe Inn Glen Allen 9.6/10 Exceptional (118) "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) ![Exterior](https://images.trvl-media.com/lodging/100000000/99340000/99336800/99336779/w1087h720x0y2-3e45e540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/100000000/99340000/99336800/99336779/6b649ae7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99340000/99336800/99336779/ddc82326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99340000/99336800/99336779/20907f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Rural Retreat in Central King William County King William 10/10 Exceptional (11) "Nicest vacation home we’ve ever stayed at! House was perfectly clean and well stocked with everything we needed to make our stay comfortable. The location was quiet which was great for a peaceful weekend with family. Communication was prompt and instructions were clear and easy-going. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen R. CA $411 CA $705 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/King-William-Hotels-Private-Rural-Retreat-In-Central-King-William-County.h99336779.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 4 - Nov 5 [](https://www.expedia.ca/Richmond-Hotels-Sky-Lounge-Pool.h120825797.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) ![Interior](https://images.trvl-media.com/lodging/112000000/111250000/111249600/111249510/9dd424b6.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) ### 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 $148 CA $295 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) ![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) ![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) ![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) ### A house full of steel balls and games Dumbarton 9.6/10 Exceptional (98) "Clean, fun. and very kind and responsive owner. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marian CA $99 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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/700000/696000/695938/cf2952cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/700000/696000/695938/4878c369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![58-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/1000000/700000/696000/695938/8c762437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/700000/696000/695938/51c40e6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Richmond Marriott Short Pump Glen Allen 8.6/10 Excellent (924) "Great place very clean very comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianna CA $166 CA $193 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Richmond-Hotels-Richmond-Marriott-Short-Pump.h695938.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=2025-11-13&endDate=2025-11-14®ionId=6292&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Ashland Hotel Reviews ![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) ![The Commonwealth](//images.trvl-media.com/lodging/1000000/40000/39900/39891/901fb2f8_y.jpg) ### The Commonwealth 10/10 Excellent "Was a very nice hotel " [](https://expedia.ca/Richmond-Hotels-The-Commonwealth.h39891.Hotel-Information) ![The Berkeley Hotel](//images.trvl-media.com/lodging/1000000/10000/1900/1860/2c75da2c_y.jpg) ### The Berkeley Hotel 10/10 Excellent "Clean but needs updating. I definitely expected more as far as comfortable bed, linens." [](https://expedia.ca/Richmond-Hotels-The-Berkeley-Hotel.h1860.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 "Great location!! Everything you need is nearby! " [](https://expedia.ca/Richmond-Hotels-Hyatt-Place-Richmond-Airport.h2385332.Hotel-Information) ![Holiday Inn Express Richmond - Midtown by IHG](//images.trvl-media.com/lodging/1000000/30000/24700/24653/a35e3702_y.jpg) ### Holiday Inn Express Richmond - Midtown by IHG 10/10 Excellent "The run was very clean and spacious. We didn’t hear any noises from other rooms. The staff were very friendly. Lots of parking. Will start here again. " [](https://expedia.ca/Richmond-Hotels-Holiday-Inn-Express-Richmond-Midtown.h24653.Hotel-Information) ![Regency Inn Richmond](//images.trvl-media.com/lodging/1000000/20000/13900/13851/d4110985_y.jpg) ### Regency Inn Richmond 10/10 Excellent "The front desk staff are absolutely amazing! The definitely went above and beyond when you need assistance. " [](https://expedia.ca/Richmond-Hotels-Regency-Inn-Richmond.h13851.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 "Excellent customer service. Clean and comfortable hotel room." [](https://expedia.ca/Richmond-Hotels-Best-Western-Premier-Richmond-City-Gateway.h10271.Hotel-Information) ![The Jefferson Hotel](//images.trvl-media.com/lodging/10000000/9870000/9868600/9868548/c8b04136_y.jpg) ### The Jefferson Hotel 10/10 Excellent "This is a wonderful hotel, and the service is impeccable. It is a beautiful place." 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