Title: Book the Best Eastern Maryland WINERY Hotels in 2025 | Expedia.ca [Eastern Maryland Travel Guide](https://expedia.ca/Eastern-Maryland.dx6057488)[Hotels in Eastern Maryland](https://expedia.ca/Eastern-Maryland-Hotels.d6057488.Travel-Guide-Hotels)[Vacation Rentals in Eastern Maryland](https://expedia.ca/Eastern-Maryland-Vacation-Rentals.d6057488.Travel-Guide-VacationRentals)[Flights to Eastern Maryland](https://expedia.ca/Cheap-Flights-To-Eastern-Maryland.d6057488.Travel-Guide-Flights)[Things to do in Eastern Maryland](https://expedia.ca/Things-To-Do-In-Eastern-Maryland.d6057488.Travel-Guide-Activities)[Eastern Maryland Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Maryland.d6057488.Car-Rental-Guide)[Eastern Maryland Vacation Packages](https://expedia.ca/Eastern-Maryland.d6057488.Destination-Travel-Guides) ![Long Wharf Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253260-Eastern-Maryland.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Eastern Maryland, MD ![](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 Eastern Maryland Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6057488&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6057488&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6057488&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=6057488&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Maryland Winery Hotels ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2557x3y4-d297081d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/72680920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/8cb72b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2546x3y0-2a92d744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City 9.0/10 Wonderful (1566) "Great property , large rooms and free breakfast!" CA $118 CA $131 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/08f08113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/607bb91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/fcecd38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/eb718924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Place Hotel Downtown Ocean City 9.2/10 Wonderful (1008) "Nice place, great staff." CA $61 CA $110 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (828) "Great service. Very clean." CA $143 CA $159 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/37b6becc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/7004874c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/3c6abce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/a57ab64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast Salisbury 10/10 Exceptional (159) "An absolute gem of a stay. I will definitely be back! A perfect stop for an affordable and nice stay on your way to beach the next day!" CA $190 CA $212 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/53a12ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/c89c29dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/29297346.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/4f3138fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Ocean City Oceanfront Downtown Ocean City 9.2/10 Wonderful (980) "Great hotel and service " CA $135 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.Hotel-Information) ![Standard Room, 2 Queen Beds, Oceanfront | Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/50868563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/298c40df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/9e9c92ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/52e157e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaLoft Oceanfront Hotel Midtown Ocean City 8.6/10 Excellent (366) "Great time with the family. Super walkable and beach front! " CA $111 CA $123 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Ocean-City-Hotels-Atlantic-OceanFront-Inn.h3660765.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/a3a4bc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/f42afa08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/7762f1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking, Bay View](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/c80a3acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1007) "Great place to stay! " CA $95 CA $106 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/a4c59418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1f3f9838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/96859422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/71bdd057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air Bel Air 9.2/10 Wonderful (216) "Friendly staff, clean hotel " CA $164 CA $184 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/8bf1c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/9b7ea9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/08a34731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/w3633h2233x0y0-164d7bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Monte Carlo Ocean City Downtown Ocean City 7.8/10 Good (1012) "We stayed for the week and it was an excellent stay!" CA $78 CA $115 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Ocean-City-Hotels-Hotel-Monte-Carlo-Ocean-City.h1866913.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/4791e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/c1ae5468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/3618b010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/a5883b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quarry Landing - Center of Town & River View - 3 Bedroom Port Deposit 9.8/10 Exceptional (9) "Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙" CA $208 CA $324 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Port-Deposit-Hotels-Cheerful-3-Bedroom-Cottage-In-The-Center-Of-Town-Located-On-High-Street.h82880842.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=2025-10-29&endDate=2025-10-30®ionId=6057488&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Maryland Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Salisbury](https://www.expedia.ca/4Star-Salisbury-Hotels.s40-0-d6057491.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Bivalve](https://www.expedia.ca/Bivalve-Hotels-Hotel-With-Pool.0-0-d553248635975846907-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels near Centre at Salisbury](https://www.expedia.ca/Centre-At-Salisbury-Hotels.0-l6172462-0.Travel-Guide-Filter-Hotels) - 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