Title: Book the Best Ocean Pines WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in Berlin](https://expedia.ca/Berlin-Vacation-Rentals.d79155.Travel-Guide-VacationRentals)[Flights to Berlin](https://expedia.ca/Cheap-Flights-To-Berlin.d79155.Travel-Guide-Flights)[Things to do in Berlin](https://expedia.ca/Things-To-Do-In-Berlin.d79155.Travel-Guide-Activities)[Ocean Pines Car Rentals](https://expedia.ca/Car-Rentals-In-Ocean-Pines.d6287096.Car-Rental-Guide)[Ocean Pines Vacations](https://expedia.ca/Ocean-Pines.d6287096.Destination-Travel-Guides) ![The morning after a frigid snow storm went through this retirement community, icy streets and a cold sky with rows of houses and christmas decorations](https://images.trvl-media.com/place/6287096/28b96d51-60a2-469a-9c05-52f60163ce77.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Ocean Pines, MD from CA $97 - ![](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 Ocean Pines Winery Hotels Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6287096&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=6287096&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6287096&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6287096&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ocean Pines hotels with winery ![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) ![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) ![On the beach](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/01fa9013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (1590) "Room was very clean, staff were the best.would definitely recommend staying there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $110 CA $122 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/eb718924.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) ### Park Place Hotel [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (1053) "Great location, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yun-Ping [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Oceanfront 1st Floor | View from room](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/3f0d63a5.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) ![Lobby](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) ### Courtyard Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (1002) "Amazing hotel and staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorielen CA $120 CA $133 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.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) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/d3caf33c.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) ![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 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) North Ocean City 8.2/10 Very good (1001) "Our stay was amazing. The rom was spacious and clean. The lobby was decorated so cute for the holidays makkng it very welcoming. Staff was so kind and helpful. Pool was clean and eat to access." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy CA $87 CA $97 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/50000000/49180000/49178600/49178587/af034c0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/50000000/49180000/49178600/49178587/49834831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49180000/49178600/49178587/7b2adfe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/50000000/49180000/49178600/49178587/019e05c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-IV-Downtown-Waterfront.h49178587.Hotel-Information) Downtown Ocean City 9.8/10 Exceptional (62) "The condo was very convenient to get to the beach. Beautiful view of the bay. Plenty of room for everyone to enjoy the stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David H. CA $67 CA $486 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-IV-Downtown-Waterfront.h49178587.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/19000000/18790000/18785800/18785781/53d8f7df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18790000/18785800/18785781/6592e12c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18790000/18785800/18785781/w1080h810x0y765-b38c97dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18790000/18785800/18785781/a0af18d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### "FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL"" [](https://www.expedia.ca/Selbyville-Hotels-FENWICK-ISL-WATERFRONT-VACATION-HOME-AT-THE-BEACH-W-BOAT-DOCK.h18785781.Hotel-Information) Selbyville 9.2/10 Wonderful (118) "Plenty of room, and everything you need for a few nights." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael A. CA $72 CA $307 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Selbyville-Hotels-FENWICK-ISL-WATERFRONT-VACATION-HOME-AT-THE-BEACH-W-BOAT-DOCK.h18785781.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/b7fb23e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/ca6a09e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/6ab2a88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/ed397077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Paradise VII-Brand New Luxury Townhouse with Pool, Garage, and Water View [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-VII-Brand-New-Luxury-Townhouse-With-Pool.h71927597.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (19) "Really nice place,had everything we needed very elegant and relaxing,tvs nice and updated will come back again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George H. CA $67 CA $425 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-VII-Brand-New-Luxury-Townhouse-With-Pool.h71927597.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34590000/34581400/34581331/w1164h1876x5y0-c424458c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sport court](https://images.trvl-media.com/lodging/35000000/34590000/34581400/34581331/w1170h874x0y9-809ab6b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/35000000/34590000/34581400/34581331/c99799d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34581400/34581331/w1170h1550x0y0-e23dab4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean calling & country concert availability! [](https://www.expedia.ca/Ocean-City-Hotels-Located-Next-To-Park.h34581331.Hotel-Information) North Ocean City 9.0/10 Wonderful (35) "We really enjoyed our stay here! Close to the beach and in walking distance of a lot of activities but also very quiet! Loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee P. CA $74 CA $268 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Ocean-City-Hotels-Located-Next-To-Park.h34581331.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/12c14ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/4bc17011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/9fcb2277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/e198f6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Main Street - Apartment C - Berlin, MD [](https://www.expedia.ca/Ocean-City-Hotels-On-Main-Street-Apartment-Berlin.h64657840.Hotel-Information) Downtown Berlin 9.4/10 Exceptional (28) "We loved everything about our stay! This place is adorable and the location is awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kelly K. CA $95 CA $309 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Ocean-City-Hotels-On-Main-Street-Apartment-Berlin.h64657840.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/32000000/31190000/31186800/31186770/d73cb96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31190000/31186800/31186770/53c6c5bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31190000/31186800/31186770/d720009a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/32000000/31190000/31186800/31186770/d0001eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location! [](https://www.expedia.ca/Ocean-City-Hotels-Mid-Town-OceanSideBlock-46th-St-Sleeps-5-Location.h31186770.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (123) "We loved it here so much! It was perfect for my family of 5! We will be back next year!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley S. CA $172 CA $330 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Ocean-City-Hotels-Mid-Town-OceanSideBlock-46th-St-Sleeps-5-Location.h31186770.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=2025-12-27&endDate=2025-12-28®ionId=6287096&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Ocean Pines Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [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) - [B&B in Bishopville ](https://www.expedia.ca/Bishopville-Bed-And-Breakfast.d3000440430-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Bishopville ](https://www.expedia.ca/Bishopville-Hotels-Cheap-Hotels.0-0-d3000440430-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bishopville ](https://www.expedia.ca/Bishopville-Hotels-Luxury-Hotel.0-0-d3000440430-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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