Title: Book the Best Chestertown FAMILY FRIENDLY Hotels from CA $108 - Kid-Friendly Hotels in Chestertown, MD | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Family Hotels in Chestertown, MD from CA $108 ![](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 Chestertown Family Hotels Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=family_friendly) ## Top Chestertown Family Hotels ![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) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.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) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (835) "The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie CA $142 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown 7.2/10 Good (409) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $100 CA $111 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/73e21a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (105) "A charming studio in a quiet neighborhood. great directions from host on how to use the property - " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $138 CA $222 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/fc8d3076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/270b1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/038e56e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/ff521238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly restored apartment in the heart of Chestertown Chestertown 9.8/10 Exceptional (27) "Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!"" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maggie D. CA $460 CA $674 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Chestertown-Hotels-Newly-Restored-Apartment-In-The-Heart-Of-Chestertown.h90876079.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a8370cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/9d10475b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a5912d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG Aberdeen 9.0/10 Wonderful (1007) "Loved our stay! Will visit again soon!!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meagan CA $129 CA $145 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fe97576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (298) "One of the best hotels I have ever stayed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jean CA $151 CA $167 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/w1822h1320x8y2-6d9bb9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/87321239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/5bd2f8c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Accessible, Non Smoking (Mobility, Roll-In Shower)](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/7b28496f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area Edgewood 7.2/10 Good (1011) "I found the staff to be very friendly, I believe that it is a family owned / operated establishment and while the inside of the hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natasha CA $96 CA $108 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Edgewood-Hotels-Wingate-By-Wyndham-Bel-Air-I-95-Exit-77A.h56432.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/726148e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown Middletown 8.8/10 Excellent (846) "Enjoyed the amenities and great location for shops nearby " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica CA $145 CA $161 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/48d9bd9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville 7.8/10 Good (845) "Great place and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rhonda CA $136 CA $151 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.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) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (909) "Nice Holiday Inn Express with great water views." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $144 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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=2025-11-13&endDate=2025-11-14®ionId=7215&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "I liked the breakfast because it had cold stuff. And good hot food. Eggs Sausage waffles and juice. " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "Clean room and quiet enough to sleep through the afternoon. " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Lovely room" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](//images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Great place to stay" [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](//images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "Will definitely be back again 🙌" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](//images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable." [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Americas Best Value Inn Edgewood](//images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "Staff" [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly. " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Frequently asked questions ### What's Chestertown like for family-friendly vacations? > If you've been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and sporting events are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. ### What's the best place to stay when traveling with kids to Chestertown? > [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) is another good option for your family trip. ### When's the best time to book a family-friendly vacation in Chestertown? > The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches. ### What's there to see and do with your family in Chestertown? > While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. 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