Title: Chestertown Cottages from CA $581 | 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) ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Search Chestertown Cottage Rentals from CA $581 - ![](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 [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-03-06&endDate=2026-03-08&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/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/aa5cdca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/5c7724f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Rosedale [](https://www.expedia.ca/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.Hotel-Information) 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 CA $220 CA $690 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/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) ![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) ![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) ### Cottage in Betterton [](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) CA $312 CA $581 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/7f38e3aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/dcb17a56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/37ea1a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/489a1c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Stevensville [](https://www.expedia.ca/Stevensville-Hotels-Charming-2-Bedroom-Waterfront-Cottage-In-Peaceful-Stevensville-With-AC.h108008595.Hotel-Information) 10/10 Exceptional (6 reviews) "Beautiful home. Very nice and quiet neighborhood on the water. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shannan t. CA $553 CA $1,215 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Stevensville-Hotels-Charming-2-Bedroom-Waterfront-Cottage-In-Peaceful-Stevensville-With-AC.h108008595.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) ![Exterior](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/a2c5e148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/58000000/57720000/57720000/57719943/2f9f691d.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) ### Cottage in Pasadena [](https://www.expedia.ca/Pasadena-Hotels-Chesapeake-Cottages-2-Quaint-Waterfront-Retreats.h57719943.Hotel-Information) 9.6/10 Exceptional (22 reviews) "Excellent Property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Buu T. CA $499 CA $922 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/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) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w950h680x38y3-96439ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Historic District [](https://www.expedia.ca/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) 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. CA $414 CA $761 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-01-24&endDate=2026-01-25®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Cottages.d7215-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![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 "Yes breakfast was fresh but I would prefer real eggs. I don’t like those eggs. Other than that it was good. Parking is great. You might want to get more lighting on the side of the building. Other than that I LOVE my stay at Holiday Inn Express. " [](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 "Everything was clea" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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 "NA" [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Spotless hotel, staff was beyond incredible. They have won a customer for llife" [](https://expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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 "Delicious breakfast and very spacious rooms. " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.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 "Everything at the hotel was excellent. We had a small dog with us and they were very accommodating. And the breakfast over several days was varied and excellent." [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Front desk staff and breakfast staff" [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "The hotel was beautiful, and the staff was courteous and friendly. " [](https://expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Very welcoming and room very clean." [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ## Find out more about Chestertown ## Chestertown Cottages information | Number of reviews | 18 | | ----------------- | ----------- | | Accommodation | 62 Cottages | | Lowest Price | CA $581 | | Highest Price | CA $1,215 | ## 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 Rental - More ways to book - [Best Western Hotels in Aberdeen Proving Ground ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels-Best-Western.0-0-d553248634999428212--bBestWestern.Travel-Guide-Filter-Hotels) - [Aberdeen Proving Ground Hotels ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels.d553248634999428212.Travel-Guide-Hotels) - [Apartments in Betterton ](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - 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