Title: Chestertown, MD Cottage Rentals from $422 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7215/2127ed08-151b-4865-9870-3d0463a3d88b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=7215&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown cottages ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/8b7ab73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/w1474h1242x2y0-82b785fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/a2c5e148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/90-1f5b873c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Cottages- 2 Quaint Waterfront Retreats [](https://www.expedia.com/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) Pasadena 9.6/10 Exceptional (22 reviews) "Excellent Property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Buu T. $583 nightly $665 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-350049dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-479799f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-414422dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-f666fabb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grandma’s Cottage will wrap around you like a warm hug [](https://www.expedia.com/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) Betterton $398 nightly $422 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h447x0y118-8b5ab4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h640x0y22-f248bc40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/afea8523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w951h680x36y3-968871c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cozy Cottage in Historic Downtown [](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) Historic District 9.6/10 Exceptional (16 reviews) "This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda Q. $506 nightly $577 total Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.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.com/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AA_SPRING_PROMO_7215) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=COTTAGE) Cabins [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CABIN) Condos [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=CONDO) Apartments [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=APARTMENT) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=HOUSE_BOAT) Villas [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=VILLA) Residences [](https://www.expedia.com/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-06-07&d1=2026-06-07&endDate=2026-06-10&d2=2026-06-10&lodging=RESIDENCE) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/c6a165a6_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 8/10 Good "We chose this property because we were traveling with our dog. The property and facilities were very adequate, room was large, very clean and comfortable bed. Staff was very friendly and helpful. Breakfast was great, husband loves eggs and there were scrambled eggs. Our only complaint is that people do not pick up their dog poops. Would come back! Anne " [](https://expedia.com/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/38012dd1_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "fast check in " [](https://expedia.com/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/5d79a398_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 6/10 Okay "Expedia need to work better with their affiliates. I booked for a room for 5 people and when we got there they said they don't have such room. I paid for 2 nights but did a late checked in the morning after the first night. I requested a cot then and 4 more times after that. We did not get our cot till almost 10 on our last night." [](https://expedia.com/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/c35aa4df_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 4/10 Poor "When I checked in at 7 pm there was no one at the reception desk and I had to wait 15 for someone to arrive. The parking directions he provided were very complicated. The coffee shop had an extremely limited menu and hours and the staff was frequently unavailable for about 10 minutes." [](https://expedia.com/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Country Inn & Suites by Radisson, Baltimore North, MD](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16_y.jpg) ### Country Inn & Suites by Radisson, Baltimore North, MD 2/10 Terrible "This hotel is poorly ran. The employees are friendly enough but with the negative news they deliver who would blame them if they hated their jobs. The pool and hot tub are not working. When you say anything they say well you can go somewhere else. The sheets and towels are all stained. The breakfast is absolutely horrendous. This place needs to have a change of management and get the necessary upgrades." [](https://expedia.com/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Staying is peaceful and the rooms clean." [](https://expedia.com/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Very clean, great staff, very good communication skills, excellent service, AC could have been turned on sooner, friendly. I just wish they had a restaurant on the premises." [](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Awesome stay, hotel is spacious, clean, modern and great location, close to everything. Plenty of free parking as well, I would 100% stay again!" [](https://expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "The hotel was great. The room was clean and spacious. The staff made us feel welcome." [](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Find out more about Chestertown ## Chestertown Cottages information | Number of reviews | 16 | | ----------------- | ----------- | | Accommodation | 62 Cottages | | Lowest Price | $422 | | Highest Price | $665 | ## Frequently asked questions ### Why book your cottage in Chestertown with Expedia? ### How can I find cheap cottages in Chestertown? ### What is there to do in Chestertown near my cottage? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - [Hotels near Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) - 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