Title: Chestertown Motel: Browse Cheap Motels in Chestertown 2025 | 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) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Motels in Chestertown - ![](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 prices for these dates Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown Motels ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/9caa403f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/056aa897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/06910f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23100/23024/d468abf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Aberdeen Aberdeen 7.0/10 Good (907) "Stayed here numerous time, friendly staff, easy check in, quick breakfast, clean room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brett CA $85 CA $95 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/180b8972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/a1cb4d24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/5177cf8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking (One-Bedroom)](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/fb66f5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Aberdeen MD Aberdeen 7.0/10 Good (854) "Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly CA $73 CA $82 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/335c1120.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/8f46f567.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/b510cc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/540000/530300/530229/516c17a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Village Inn Annapolis MD Annapolis 6.2/10 (506) "The room was very nice, clean and quiet. Great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $117 CA $133 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/304c53d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/0707a932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/61b9d981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Baltimore/Essex Area Essex 5.4/10 (405) "Just a nice quiet cool place clean rooms and the bed is away from the door lol" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamelle CA $118 CA $137 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.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=2025-12-07&endDate=2025-12-08®ionId=7215&adults=2&lodging=MOTEL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_7215) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Motels.d7215-aaMotels.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 10/10 Excellent "Very friendly staff and quick check in. The hotel is very nice and clean. " [](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "room was clean but the shower curtain was in tatters. multiple rings torn off" [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 10/10 Excellent "Nice rooms, quiet location, good staff" [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg) ### Hampton Inn Baltimore Bayview Campus 10/10 Excellent "All of the above. " [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://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 "yes" [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "." [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Pretty clean and nice. Kids enjoyed the pool. Overall it was pretty good!" [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Good location. Very pricey but not much competition " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Find out more about Chestertown ## Chestertown Motels information | Number of reviews | | | --- | --- | | Accommodation | Motels | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### What can I expect from a motel trip to Chestertown? > If you're having difficulty finding a motel in Chestertown, consider some of the motels we suggest around the area or let us help you find something similar from over 39 hotels and other lodging options. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free parking and free breakfast. ### What's it like to stay in a motel? > At most motels, you're likely to find an outdoor pool and a free parking spot. When you stay at a motel, you'll often have access to your room from an outside corridor overlooking the parking lot. Motels began in the 1920s as a convenient place to stay for the weary traveler taking a road trip along America's major roadways. ### What are the best motels in Chestertown? > Here you'll find some of our customers' favorite motels to choose from in the larger area. [Driftwood Inn](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information): Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. [Days Inn by Wyndham Aberdeen](https://www.expedia.ca/Aberdeen-Hotels-Days-Inn-By-Wyndham-Aberdeen.h23024.Hotel-Information): A seasonal outdoor pool along with freebies like breakfast, WiFi, and parking are available during your stay. Central Chestertown is 21.8 mi (35.1 km) away. [Super 8 by Wyndham Baltimore/Essex Area](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information): Enjoy the in-room free WiFi, and freebies including breakfast, parking, and a cruise ship terminal shuttle. Located 21.8 mi (35 km) from the heart of Chestertown. [Super 8 by Wyndham Aberdeen MD](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information): Central Chestertown is 21.8 mi (35.1 km) away. A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. [Village Inn Annapolis MD](https://www.expedia.ca/Annapolis-Hotels-Village-Inn.h530229.Hotel-Information): 25.6 mi (41.1 km) from the heart of Chestertown. Enjoy access to the laundry facilities, and freebies including WiFi and parking. ### What can I do in Chestertown? > These are some of the parks and outdoorsy places: Northern Chesapeake Bay, Chesapeake Bay, and Chestertown Dog Park. You'll find these family-friendly attractions in the area: Crumpton Auction and Hazel Miner Monument. During your trip, here are some other places to visit: Historical Society of Kent County Maryland, Chestertown Historic District, and Rolphs Wharf Marina. ### What's the seasonal weather like in Chestertown? > Weather can make or break a roadtrip, so we've gathered some data about year-round temperatures in Chestertown to help you plan yours. 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 are my options for getting around Chestertown when staying in a motel? > We've gathered some information about local transportation options in Chestertown to help you navigate your stay: Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the heart of the city. Otherwise, look for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. 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