Title: Best Cottages in Chestertown in 2026 | Expedia.co.uk [Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d7215.Car-Hire-Guide)[Chestertown Holidays](https://expedia.co.uk/Chestertown.d7215.Holidays-City-Breaks) ![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) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 In two weeks [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [8 May - 10 May](https://www.expedia.co.uk/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 four months [5 Jun - 7 Jun](https://www.expedia.co.uk/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) ## Our top choices for Chestertown cottages ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/d5fde131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/aa5cdca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/a6ee7c11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/5c7724f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Mi to Downtown Baltimore: Quiet Home w/ Porch [](https://www.expedia.co.uk/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.Hotel-Information) Rosedale 9.0/10 Wonderful (2 reviews) "It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy £385 includes taxes & fees 28 Feb - 1 Mar [](https://www.expedia.co.uk/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.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) ![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) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-e0efb6c3.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) ### Grandma’s Cottage will wrap around you like a warm hug [](https://www.expedia.co.uk/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) Betterton £311 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/8b7ab73b.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/a2c5e148.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) ### Chesapeake Cottages- 2 Quaint Waterfront Retreats [](https://www.expedia.co.uk/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. £520 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.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.co.uk/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) Historic District 9.6/10 Exceptional (16 reviews) "Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael C. £418 includes taxes & fees 16 Feb - 17 Feb [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02®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-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_7215) ## Find holiday rentals that suit your style Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=HOUSE_BOAT) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VILLA) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Great hotel, across from State House. Restaurants within walking distance. Great little town, can’t wait to visit again . " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 10/10 Excellent "Awesome" [](https://expedia.co.uk/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.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 "Room was clean and was very satisfied with my stay." [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://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 "It was quiet and very clean‼️" [](https://expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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 "Yes it was excellent" [](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![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 "Excellent service at front desk and spotless room " [](https://expedia.co.uk/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "The best Inn in Edgewood " [](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "My room was clean and in order. Being a guest at this hotel multiple times in the past, I’m still greeted with kindness and respect and I love the staff that works there: everyone is friendly, and will fulfill any needs when asked. A truly “satisfying” guest experience staying at the Fairfield Inn and Suites by Marriot in White Marsh, Maryland." [](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "Staff and room were amazing" [](https://expedia.co.uk/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ## Find out more about Chestertown ## Chestertown Cottages information | Number of reviews | 18 | | ----------------- | ----------- | | Accommodation | 62 Cottages | | Lowest Price | £311 | | Highest Price | £520 | ## 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 - More ways to book - [Book Cottages in Chestertown on Expedia.com ](https://www.expedia.com/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)