Title: Book the Best Montego Bay WINERY Hotels in 2026 | Expedia.ca [Vacation Rentals in Ocean City](https://expedia.ca/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)[Flights to Ocean City](https://expedia.ca/Cheap-Flights-To-Ocean-City.d9151.Travel-Guide-Flights)[Things to do in Ocean City](https://expedia.ca/Things-To-Do-In-Ocean-City.d9151.Travel-Guide-Activities)[Montego Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Montego-Bay.d553248635976479127.Car-Rental-Guide)[Montego Bay Vacations](https://expedia.ca/Montego-Bay.d553248635976479127.Destination-Travel-Guides) ![Assateague Island Wild Ponies on the Beach](https://images.trvl-media.com/place/553248635976479127/e0dbbd5e-3261-4bdf-8ca4-d3650dac5032.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Montego Bay, MD from CA $92 - ![](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 Montego Bay Winery Hotels Tonight [Dec 4 - Dec 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-04&endDate=2025-12-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976479127&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Montego Bay 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) ![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) ![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 (1044) "Excellent spot, clean, amazing views. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sacra CA $70 CA $92 total includes taxes & fees Jan 4 - Jan 5, 2026 [](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) ![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) ![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) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City 9.0/10 Wonderful (1589) "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 $112 CA $124 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.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) ![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/3000000/2480000/2475100/2475053/53a12ce9.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) ### Courtyard Ocean City Oceanfront 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 $121 CA $135 total includes taxes & fees Dec 10 - Dec 11 [](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) ![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) ![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) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1000) "Very safe and great staff. Gave us all the Christmas light locations. Their lobby was the absolute cutest!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie CA $94 CA $104 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.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) ![Marina](https://images.trvl-media.com/lodging/19000000/18790000/18785800/18785781/w1080h810x0y765-2ceead12.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) ![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) ### "FENWICK ISL. WATERFRONT VACATION HOME AT THE BEACH W / BOAT DOCK, RAMP & POOL"" 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 $74 CA $314 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Selbyville-Hotels-FENWICK-ISL-WATERFRONT-VACATION-HOME-AT-THE-BEACH-W-BOAT-DOCK.h18785781.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 Downtown Ocean City 9.8/10 Exceptional (62) "Perfect family beach house, we had a blast! Our family of 7 stayed for 3 nights. We loved the easy check-in, location, and spacious, clean condo. Thank you for letting us use your gorgeous home Kim, we really enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy R. CA $68 CA $494 total includes taxes & fees Dec 8 - Dec 9 [](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) ![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) ![Interior](https://images.trvl-media.com/lodging/72000000/71930000/71927600/71927597/ca6a09e9.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) ### 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 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George H. CA $68 CA $426 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Ocean-City-Hotels-Beach-Paradise-VII-Brand-New-Luxury-Townhouse-With-Pool.h71927597.Hotel-Information) ![Pet-friendly](https://images.trvl-media.com/lodging/10000000/9810000/9801700/9801688/e2911dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9810000/9801700/9801688/4579f5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/10000000/9810000/9801700/9801688/02cfd166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family dining](https://images.trvl-media.com/lodging/10000000/9810000/9801700/9801688/b21020d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canalside Inn Canal 9.0/10 Wonderful (251) "Dog friendly, great setting, and highly responsive staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $189 CA $220 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Rehoboth-Beach-Hotels-Canalside-Inn.h9801688.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/w1170h1550x0y0-e23dab4e.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) ### Ocean calling & country concert availability! North Ocean City 9.0/10 Wonderful (35) "Everything was as stated. We had zero issues and everything was great. Perfect for a family getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James R. CA $75 CA $271 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Ocean-City-Hotels-Located-Next-To-Park.h34581331.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/73000000/72340000/72334100/72334027/775868d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72340000/72334100/72334027/d95a5e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/73000000/72340000/72334100/72334027/d34cdc03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/73000000/72340000/72334100/72334027/a38f85a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### IslandCoveParadise: Luxury-NewlyBuiltTH! OnTheWater-Boardwalk-Pool-w/2 CarGarage Downtown Ocean City 10/10 Exceptional (16) "Very responsive hosts. Home is convenient to all the major happenings in OCMD. It has all the amenities and fully stocked kitchen with everything we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Conswella O. CA $138 CA $553 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Ocean-City-Hotels-IslandCoveParadise-NewlyBuiltOnTheWaterBoatSlipPoolBoardwalk2CarGarage.h72334027.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=2025-12-18&endDate=2025-12-19®ionId=553248635976479127&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Montego Bay Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [B&B in Bishopville ](https://www.expedia.ca/Bishopville-Bed-And-Breakfast.d3000440430-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Bishopville Hotels ](https://www.expedia.ca/Bishopville-Hotels.d3000440430.Travel-Guide-Hotels) - [Mountain Hotels in Caine Woods ](https://www.expedia.ca/Caine-Woods-Ocean-City-Hotels-Mountain-Hotels.0-n553248635976482130-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Caine Woods ](https://www.expedia.ca/Caine-Woods-Ocean-City-Hotels-Pet-Friendly-Hotel.0-n553248635976482130-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Caine Woods Hotels ](https://www.expedia.ca/Caine-Woods-Ocean-City-Hotels.0-n553248635976482130-0.Travel-Guide-Filter-Hotels) - 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