Title: Book the Best Assateague Pointe WINERY Hotels in 2025 | 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)[Assateague Pointe Car Rentals](https://expedia.ca/Car-Rentals-In-Assateague-Pointe.d553248635976473325.Car-Rental-Guide)[Assateague Pointe Vacations](https://expedia.ca/Assateague-Pointe.d553248635976473325.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Assateague Pointe, MD from CA $106 ![](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 Assateague Pointe Winery Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976473325&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473325&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976473325&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473325&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Assateague Pointe Winery Hotels ![Sundeck](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/08f08113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/d6974a18.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) ### Park Place Hotel Downtown Ocean City 9.2/10 Wonderful (1006) "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) ![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) ![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 Downtown Ocean City 9.0/10 Wonderful (1563) "Great property , large rooms and free breakfast!" CA $118 CA $131 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/4d4115e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaLoft Oceanfront Hotel Midtown Ocean City 8.6/10 Excellent (364) "Great time with the family. Super walkable and beach front! " CA $111 CA $123 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/7762f1e3.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) ![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) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1006) "Great place to stay! " CA $95 CA $106 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/4f3138fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony, Oceanfront (Hearing Accessible)](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/0f74ca55.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) ### Courtyard Ocean City Oceanfront Downtown Ocean City 9.2/10 Wonderful (980) "Great hotel and service " CA $134 CA $149 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.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) ![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) ![Rooftop terrace](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/9b7ea9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, Balcony, Partial Ocean View](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/5a5080ec.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 $90 CA $127 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ocean-City-Hotels-Hotel-Monte-Carlo-Ocean-City.h1866913.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) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49180000/49178600/49178587/97b30a2e.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) ![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) ### Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo Downtown Ocean City 9.8/10 Exceptional (56) "We had such a great time with such a beautiful view. Rooms were well kept and very nice. Overall 10 out of 10." CA $69 CA $496 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-IV-Downtown-Waterfront.h49178587.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) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/a75124d8.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) ![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 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 " CA $69 CA $434 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34590000/34581400/34581331/76049359.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) ![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! North Ocean City 9.0/10 Wonderful (33) "We were staying at the condo for my daughter’s softball tournament. The location was perfect, since it was next to the fields and out of the routine congestion. I was also happy with the cleanliness of the condo. " CA $76 CA $274 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Ocean-City-Hotels-Located-Next-To-Park.h34581331.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/12000000/11210000/11205500/11205496/6d09e882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11210000/11205500/11205496/0dc24e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11210000/11205500/11205496/e96a2c73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, blackout drapes, free WiFi, bed sheets](https://images.trvl-media.com/lodging/12000000/11210000/11205500/11205496/d7cb1974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fish Tales Boardwalk Inn Downtown Ocean City 7.6/10 Good (108) "my stay was flawless!!! " [](https://www.expedia.ca/Ocean-City-Hotels-Fish-Tales-Boardwalk-Inn.h11205496.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=2025-10-27&endDate=2025-10-28®ionId=553248635976473325&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Assateague Pointe Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [2 Star Hotels in Bayside](https://www.expedia.ca/2Star-Bayside-Berlin-Hotels.s20-n553248635976480916-0.Travel-Guide-Filter-Hotels) - [Hotels near Assateague State Park](https://www.expedia.ca/Assateague-State-Park-Hotels.0-l6075488-0.Travel-Guide-Filter-Hotels) - [Casino Hotels in Bayside](https://www.expedia.ca/Bayside-Berlin-Hotels-Casino-Hotel.0-n553248635976480916-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Bayside](https://www.expedia.ca/Bayside-Berlin-Hotels-Hotels-With-Childcare.0-n553248635976480916-0-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Bayside](https://www.expedia.ca/Bayside-Berlin-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976480916-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - 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[Hotels near Ripley's Believe It or Not!](https://www.expedia.ca/Ripleys-Believe-It-Or-Not-Hotels.0-l6075480-0.Travel-Guide-Filter-Hotels) - [Hotels near Sunset Park](https://www.expedia.ca/Sunset-Park-Hotels.0-l553248634979319162-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Adults-Only-Resorts.0-n6290283-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Beach-Hotel.0-n6290283-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Business Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Business-Hotel.0-n6290283-0-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Cheap-Hotels.0-n6290283-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Historic-Hotel.0-n6290283-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Hotels-With-A-Lazy-River.0-n6290283-0-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Hotels-With-Smoking-Rooms.0-n6290283-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Luxury Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Luxury-Hotel.0-n6290283-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Oceanfront-Hotels.0-n6290283-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in West Ocean City](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels-Waterpark-Hotels.0-n6290283-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [West Ocean City Hotels](https://www.expedia.ca/West-Ocean-City-Ocean-City-Hotels.0-n6290283-0.Travel-Guide-Filter-Hotels) - [Flights to Ocean City Municipal](https://www.expedia.ca/Cheap-Flights-To-Ocean-City-Municipal.d6030734.Travel-Guide-Flights) - [Flights to Ocean City](https://www.expedia.ca/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights) - [Flights from Ocean City](https://www.expedia.ca/lp/flights/9151/flights-from-ocean-city) - [Flights from Hartford (BDL) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/bdl/oce/hartford-to-ocean-city) - [Flights from Bradford (BFD) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/bfd/oce/bradford-to-ocean-city) - [Flights from Buffalo (BUF) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/buf/oce/buffalo-to-ocean-city) - [Flights from Columbia (CAE) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/cae/oce/columbia-to-ocean-city) - [Flights from Wilmington (ILM) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/ilm/oce/wilmington-to-ocean-city) - [Flights from Chicago (MDW) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/mdw/oce/chicago-to-ocean-city) - [Flights from Oakland (OAK) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/oak/oce/oakland-to-ocean-city) - [Flights from Ogdensburg (OGS) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/ogs/oce/ogdensburg-to-ocean-city) - [Flights from Norwood (OWD) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/owd/oce/norwood-to-ocean-city) - [Flights from Plattsburgh (PBG) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/pbg/oce/plattsburgh-to-ocean-city) - [Flights from Stockton (SCK) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/sck/oce/stockton-to-ocean-city) - [Flights from San José (SJO) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/sjo/oce/san-jose-to-ocean-city) - [Flights from Youngstown (YNG) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yng/oce/youngstown-to-ocean-city) - [Flights from Ottawa (YOW) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yow/oce/ottawa-to-ocean-city) - [Flights from Québec (YQB) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yqb/oce/quebec-to-ocean-city) - [Flights from Toronto (YTO) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yto/oce/toronto-to-ocean-city) - [Flights from Montreal (YUL) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yul/oce/montreal-to-ocean-city) - [Flights from Vancouver (YVR) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yvr/oce/vancouver-to-ocean-city) - [Flights from Toronto (YYZ) to Ocean City (OCE)](https://www.expedia.ca/lp/flights/yyz/oce/toronto-to-ocean-city) - [Jolly Roger at the Pier](https://www.expedia.ca/Jolly-Roger-At-The-Pier-Downtown-Ocean-City.d553248621592457169.Vacation-Attraction) - [Ocean City Beach](https://www.expedia.ca/Ocean-City-Beach-North-Ocean-City.d6075473.Vacation-Attraction) - [Ocean City Boardwalk](https://www.expedia.ca/Ocean-City-Boardwalk-Downtown-Ocean-City.d6317261.Vacation-Attraction) - [Ocean City Vacations](https://www.expedia.ca/Ocean-City.d9151.Destination-Travel-Guides) - [Visit Ocean City](https://www.expedia.ca/Ocean-City.dx9151) - [Trimper's Rides](https://www.expedia.ca/Trimpers-Rides-Downtown-Ocean-City.d6075476.Vacation-Attraction) - [Car rentals near Ocean City Boardwalk](https://www.expedia.ca/Car-Rentals-In-Ocean-City-Boardwalk.d6317261.Car-Rental-Guide) - [Car rental Ocean City](https://www.expedia.ca/Car-Rentals-In-Ocean-City.d9151.Car-Rental-Guide) - [Mini Car Rentals in Ocean City](https://www.expedia.ca/Mini-Car-Rentals-In-Ocean-City.d9151-tMini.Car-Rental-Guide-Class) - [Ocean City Vacation Rentals](https://www.expedia.ca/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Things to do in Ocean City](https://www.expedia.ca/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities) - [Book Hotels in Assateague Pointe on Expedia.com](https://www.expedia.com/Assateague-Pointe-Ocean-City-Hotels-Winery-Hotel.0-n553248635976473325-0-tWineryHotel.Travel-Guide-Filter-Hotels)