Title: Book the Best Eastern Shore FAMILY FRIENDLY Hotels from CA $94 - Kid-Friendly Hotels in Eastern Shore, MD | Expedia.ca [Eastern Shore Travel Guide](https://expedia.ca/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Vacation Rentals in Eastern Shore](https://expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[Flights to Eastern Shore](https://expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.ca/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Eastern Shore Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[Eastern Shore Vacation Packages](https://expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides) ![Long Wharf Park](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Eastern Shore, MD from CA $94 - ![](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 Shore Family Hotels Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Our top choices for Eastern Shore family-friendly hotels ![Lobby](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/f8c27bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/87d2aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/1d9536e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/c2aa563f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Cambridge [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) Cambridge 8.2/10 Very good (793) "It was a nice comfortable room convenient to our travels and at a great price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $147 CA $163 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (932) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $120 CA $133 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Arcade](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/e0e83584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/df24e03e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/4cb67a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (3351) "Great place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeffrey CA $66 CA $94 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/4da4e372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/30dd84ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (674) "Great view, good ambiance all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianne CA $160 CA $178 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/a68045c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Balcony, Partial Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/9ca3b695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 4 Bedrooms, Balcony, Oceanfront | Living room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/fce3df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/49cf595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1000) "The room was clean,the staff was friendly and I enjoyed my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelvin CA $106 CA $118 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/a87f70b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/18961763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed (Safari Suite (at Tidewater House))](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tidewater Inn [](https://www.expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) Easton 8.8/10 Excellent (841) "Friendly staff, spotless room, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $247 CA $272 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) ![Children's play area - outdoor](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/c2cdf922.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/9e0f5859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/b5b24819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/dac34e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chesapeake Bay [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) Cambridge 8.8/10 Excellent (1002) "Very courteous staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $223 CA $290 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/4478d4d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/051e307b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired)](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/dc05f623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/63133e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Newark - Elkton [](https://www.expedia.ca/Elkton-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Newark-Elkton.h1283746.Hotel-Information) Elkton 9.0/10 Wonderful (1001) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $131 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Elkton-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Newark-Elkton.h1283746.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (858) "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Santa CA $143 CA $158 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Coffee shop](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/b7952863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/3fdc4106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/deae0fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/406f4e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1094) "A great clean place and the bartenders were so nice. Great staff!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cynthia CA $98 CA $109 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.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=2025-12-25&endDate=2025-12-26®ionId=6025644&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Family-friendly hotels with free breakfast in Eastern Shore ![Coffee shop](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/b7952863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/3fdc4106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/deae0fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/406f4e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1094) CA $98 CA $109 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/a68045c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Balcony, Partial Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/9ca3b695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 4 Bedrooms, Balcony, Oceanfront | Living room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/fce3df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/49cf595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1000) CA $106 CA $118 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2556x3y3-8b958879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/83b7c1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/793897ce.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) ### 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 (1589) CA $110 CA $122 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/f8c27bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/87d2aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/1d9536e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/c2aa563f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Cambridge [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) Cambridge 8.2/10 Very good (793) CA $147 CA $163 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) ![Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/9e0f5859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/b5b24819.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/dac34e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chesapeake Bay [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) Cambridge 8.8/10 Excellent (1002) CA $223 CA $290 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (932) CA $120 CA $133 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Suite, 1 Bedroom, Balcony](https://images.trvl-media.com/lodging/16000000/15230000/15228300/15228207/9196f64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15230000/15228300/15228207/5e4d4337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15230000/15228300/15228207/36d07599.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, lobby lounge](https://images.trvl-media.com/lodging/16000000/15230000/15228300/15228207/43987707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Ocean City [](https://www.expedia.ca/Ocean-City-Hotels-Residence-Inn-By-Marriott-Ocean-City.h15228207.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1000) CA $112 CA $124 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Ocean-City-Hotels-Residence-Inn-By-Marriott-Ocean-City.h15228207.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/051e307b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/444bee4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Accessible, Non Smoking (Mobility/Hearing Impaired)](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/dc05f623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/63133e10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Newark - Elkton [](https://www.expedia.ca/Elkton-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Newark-Elkton.h1283746.Hotel-Information) Elkton 9.0/10 Wonderful (1001) CA $131 CA $147 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Elkton-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Newark-Elkton.h1283746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/a80bf281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/w3840h2872x0y3-fb08b66d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Two queens terrace suite oceanfront | View from room](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/08fce822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Ocean City Oceanfront Suites [](https://www.expedia.ca/Ocean-City-Hotels-Hilton-Ocean-City-Oceanfront-Suites.h27630.Hotel-Information) Midtown Ocean City 8.8/10 Excellent (1338) CA $147 CA $163 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Ocean-City-Hotels-Hilton-Ocean-City-Oceanfront-Suites.h27630.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (858) CA $143 CA $158 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-25&endDate=2025-12-26®ionId=6025644&adults=2&travelerType=family_friendly&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Family-friendly hotels with pools in Eastern Shore ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/4cb67a0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/8ccc8362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grand Hotel Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (3351) CA $66 CA $94 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Coffee shop](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/b7952863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/3fdc4106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/deae0fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/406f4e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1094) CA $98 CA $109 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/a68045c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed, Balcony, Partial Ocean View | View from room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/9ca3b695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 4 Bedrooms, Balcony, Oceanfront | Living room](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/fce3df34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/15100/15096/49cf595a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Ocean City Oceanfront [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) Midtown Ocean City 9.0/10 Wonderful (1000) CA $106 CA $118 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ocean-City-Hotels-DoubleTree-By-Hilton-Ocean-City-Oceanfront.h15096.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2556x3y3-8b958879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/83b7c1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/793897ce.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) ### 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 (1589) CA $110 CA $122 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (932) CA $120 CA $133 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/29eaf7d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/fe6e5e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, beach views ](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/55df329a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Oceanfront](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/b145f38f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Princess Royale Oceanfront Resort [](https://www.expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information) North Ocean City 8.6/10 Excellent (2298) [](https://www.expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/f8c27bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/87d2aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/1d9536e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2010000/2007700/2007686/c2aa563f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Cambridge [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) Cambridge 8.2/10 Very good (793) CA $147 CA $163 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Cambridge-Hotels-Comfort-Inn-Suites-Cambridge.h2007686.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/b9448740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/73f091b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/7a43f17d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/dec16d5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Ocean City by IHG [](https://www.expedia.ca/Ocean-City-Hotels-Holiday-Inn-Suites-Ocean-City.h787924.Hotel-Information) Downtown Ocean City 9.6/10 Exceptional (1245) CA $123 CA $136 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Ocean-City-Hotels-Holiday-Inn-Suites-Ocean-City.h787924.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/72fa8dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Oceanfront](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/89fcb7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; beach views](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/39184c06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Oceanfront | Balcony view](https://images.trvl-media.com/lodging/1000000/20000/16200/16138/4354a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Carousel Resort Hotel & Condominiums [](https://www.expedia.ca/Ocean-City-Hotels-Carousel-Resort-Hotel-Condominiums.h16138.Hotel-Information) North Ocean City 8.0/10 Very good (1398) [](https://www.expedia.ca/Ocean-City-Hotels-Carousel-Resort-Hotel-Condominiums.h16138.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/c71224e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds (No Pets Allowed)](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/w1199h797x1y1-f09ca5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/97e80f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/0e716747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fenwick Inn [](https://www.expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) North Ocean City 8.8/10 Excellent (2000) [](https://www.expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.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=2025-12-25&endDate=2025-12-26®ionId=6025644&adults=2&travelerType=family_friendly&sort=RECOMMENDED&amenities=POOL&openPlayBack=true) ## Top Eastern Shore Hotel Reviews ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg) ### Grand Hotel Ocean City Oceanfront 10/10 Excellent "Front desk Kyle was great! Room was wonderful! Great stay!" [](https://expedia.ca/Ocean-City-Hotels-Grand-Hotel-Ocean-City-Oceanfront.h800771.Hotel-Information) ![Holiday Inn & Suites Ocean City by IHG](https://images.trvl-media.com/lodging/1000000/790000/788000/787924/701b41f3_y.jpg) ### Holiday Inn & Suites Ocean City by IHG 10/10 Excellent "Staff was friendly. Great service in restaurant. Attractively de orated for the holidays" [](https://expedia.ca/Ocean-City-Hotels-Holiday-Inn-Suites-Ocean-City.h787924.Hotel-Information) ![Fenwick Inn](https://images.trvl-media.com/lodging/1000000/70000/63000/62960/971dc050_y.jpg) ### Fenwick Inn 10/10 Excellent "The room was very clean, the pool was great, the restaurant upstairs was great and the breakfast was very good. " [](https://expedia.ca/Ocean-City-Hotels-Fenwick-Inn.h62960.Hotel-Information) ![Hilton Garden Inn Ocean City Oceanfront](https://images.trvl-media.com/lodging/8000000/7740000/7731500/7731419/10d78993_y.jpg) ### Hilton Garden Inn Ocean City Oceanfront 10/10 Excellent "The room was clean and comfortable. It was nice that the hotel has a restaurant/bar area. We enjoyed dinner there one evening. " [](https://expedia.ca/Ocean-City-Hotels-Dunes-Manor-Hotel-And-Dunes-Suites.h7731419.Hotel-Information) ![Princess Royale Oceanfront Resort](https://images.trvl-media.com/lodging/1000000/30000/22000/21981/b0fe2b94_y.jpg) ### Princess Royale Oceanfront Resort 10/10 Excellent "Everything was wonderful room was much bigger and nicer than I expected " [](https://expedia.ca/Ocean-City-Hotels-Princess-Royale-Oceanfront-Resort.h21981.Hotel-Information) ![Hilton Ocean City Oceanfront Suites](https://images.trvl-media.com/lodging/1000000/30000/27700/27630/502613d6_y.jpg) ### Hilton Ocean City Oceanfront Suites 10/10 Excellent "Location, room was clean, amenities were sufficient. Staff was accommodating. " [](https://expedia.ca/Ocean-City-Hotels-Hilton-Ocean-City-Oceanfront-Suites.h27630.Hotel-Information) ![Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/2300/2292/e439a1ab_y.jpg) ### Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront 10/10 Excellent "Great off season stay, room was clean and staff was great!" [](https://expedia.ca/Ocean-City-Hotels-Howard-Johnson-Plaza-Hotel-By-Wyndham-Ocean-City-Oceanfront.h2292.Hotel-Information) ![Comfort Inn Ocean City Boardwalk](https://images.trvl-media.com/lodging/1000000/580000/570300/570278/51e3d9bd_y.jpg) ### Comfort Inn Ocean City Boardwalk 10/10 Excellent "Great stay " [](https://expedia.ca/Ocean-City-Hotels-Comfort-Inn-Boardwalk.h570278.Hotel-Information) ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg) ### Hyatt Regency Chesapeake Bay 10/10 Excellent "Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience. 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