Title: Hotels by Independent in Chestertown from CA $78 | Expedia.ca [Chestertown Travel Guide](https://expedia.ca/Chestertown.dx7215)[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 Hotels by Independent in Chestertown from CA $78 - ![](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 Tonight [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) 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) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Independent Hotels ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/d2860230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (423) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery CA $259 CA $323 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (123) "Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chi CA $243 CA $322 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/2dabe54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Rodgers) | Bathroom](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/w491h206x3y3-e2361b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/a5510d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn Havre De Grace 9.4/10 Exceptional (526) "Wonderful stay. Will stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing Chestertown 7.8/10 Good (72) "For the price off season the room should have had better amenities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $139 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Basic Single Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/1965813e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/793857b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/bc3a3100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room](https://images.trvl-media.com/lodging/113000000/112790000/112785800/112785783/45566cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel Edgewood Edgewood 7.6/10 Good (9) "Ppl I don’t recommend u to go this place is sh!!t. Americas best. is cheap if that’s what u looking for n cleaner." ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Roger CA $69 CA $78 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Edgewood-Hotels-Motel-Edgewood.h112785783.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/03fed2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/42213387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Single Room, 1 King Bed, Bathtub, Harbour View](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/15680a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (28) "Very friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/118000000/117520000/117514500/117514499/65f8f501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/118000000/117520000/117514500/117514499/b006dbe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Harbour View](https://images.trvl-media.com/lodging/118000000/117520000/117514500/117514499/8196eb1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/118000000/117520000/117514500/117514499/c5e66f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Haven Harbour Rock Hall 8.6/10 Excellent (4) "Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne [](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Haven-Harbour.h117514499.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/85b5182c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/w1290h969x0y4-ceff4309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathtub, towels](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/w1290h1713x0y0-d518f5f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double or Twin Room](https://images.trvl-media.com/lodging/90000000/89680000/89677400/89677382/db980bf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax Inn Smyrna Smyrna 7.8/10 Good (90) "The staff was great, the room was great. Everything I expected. I would definitely stay here again. It was close to the college. TV worked, and AC was running properly. Nothing bad to say about the rest inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maurice CA $112 CA $125 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Smyrna-Hotels-Relax-Inn-Smyrna.h89677382.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/3dba8eb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/0c67a974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/w696h464x4y4-e7980281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34300000/34297800/34297781/8a65e5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! Historic District 10/10 Exceptional (238) "A great experience all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel m. [](https://www.expedia.ca/Annapolis-Hotels-Directly-Across-From-Gate-One-Steps-From-The-Waterfront.h34297781.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/201547af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/1629612c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/585f0b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, printers](https://images.trvl-media.com/lodging/104000000/103320000/103319200/103319197/ba566cbc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably Cape Saint Claire 10/10 Exceptional (38) "Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa K. [](https://www.expedia.ca/Annapolis-Hotels-Turning-Point-On-The-Little-Magothy-Large-Private-Estate.h103319197.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=2025-11-15&endDate=2025-11-16®ionId=7215&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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-Hotels-Independent.0-0-d7215--bIndependent.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels-Independent.0-0-d7215--bIndependent.Travel-Guide-Filter-Hotels) ## Top Chestertown Hotel Reviews ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Friendly and welcoming valet and front desk. Beautiful and clean rooms. Disappointed no restaurant but understand. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![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) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](//images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 10/10 Excellent "Great location and felt very safe. Very friendly staff and rooms were clean. " [](https://expedia.ca/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.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) ![Holiday Inn Express White Marsh by IHG](//images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 10/10 Excellent "Must be a new property. Clean and immaculate." 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