Title: Chesapeake City Cottages from CA $297 | Expedia.ca [Chesapeake City Travel Guide](https://expedia.ca/Chesapeake-City.dx177517)[Hotels in Chesapeake City](https://expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake City](https://expedia.ca/Chesapeake-City-Vacation-Rentals.d177517.Travel-Guide-VacationRentals)[Chesapeake City Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-City.d177517.Car-Rental-Guide)[Chesapeake City Vacation Packages](https://expedia.ca/Chesapeake-City.d177517.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/e5339e46db4549e34269a4efbbde50f5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chesapeake City Cottage Rentals from CA $297 - ![](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 In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=177517&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=177517&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) ## Browse Select Chesapeake City Cottages ![Property grounds](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/4791e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/c1ae5468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/acf287f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/3618b010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quarry Landing - Center of Town & River View - 3 Bedroom Port Deposit 9.8/10 Exceptional (10) "Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Geoff F. CA $188 CA $301 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Port-Deposit-Hotels-Cheerful-3-Bedroom-Cottage-In-The-Center-Of-Town-Located-On-High-Street.h82880842.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/0195b285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/8184389c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/37adc979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/92000000/91020000/91010800/91010763/c21874fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Thunder Hill Retreat - Spacious/Deck/Hot tub Lincoln University 10/10 Exceptional (16) "Great property, space and location for the boys and dad to have there own space, big elk creek for fishing and grill was fabulous to do chicken and burgers for a large group" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard F. CA $272 CA $669 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Thunder-Hill-Retreat-Peaceful-Sleeps-12.h91010763.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/0a987fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/1747fc02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/a383ba52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103800000/103796700/103796689/0c3a95fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland. Port Deposit 10/10 Exceptional (27) "This was our second time staying at this site. Always very clean, quiet and enjoyable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris S. CA $248 CA $297 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Unique-Cottage-Built-In-The-1800s.h103796689.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) ![Private kitchen](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-a7dcc44d.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-de4eba85.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 Betterton CA $317 CA $591 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Betterton-Hotels-Grandmas-Cottage-Will-Wrap-Around-You-Like-A-Warm-Hug.h113586648.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=2025-11-21&endDate=2025-11-22®ionId=177517&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%2FChesapeake-City-Cottages.d177517-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChesapeake-City-Cottages.d177517-aaCottages.Travel-Guide-Accommodation) ## Top Chesapeake City Hotel Reviews ![Fairfield Inn & Suites Wilmington New Castle](//images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/4b20ab4b_y.jpg) ### Fairfield Inn & Suites Wilmington New Castle 10/10 Excellent "Great experience. Bed was extremely comfortable & linens clean & soft. Would highly recommend." [](https://expedia.ca/Wilmington-Hotels-Fairfield-Inn-Suites-Wilmington-New-Castle.h8507156.Hotel-Information) ![Great Wolf Lodge Perryville](//images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/f3cb543b_y.jpg) ### Great Wolf Lodge Perryville 10/10 Excellent "Yes" [](https://expedia.ca/Perryville-Hotels-Great-Wolf-Lodge-Perryville.h103097849.Hotel-Information) ![Comfort Inn & Suites Newark - Wilmington](//images.trvl-media.com/lodging/1000000/20000/12000/11904/ea219a4a_y.jpg) ### Comfort Inn & Suites Newark - Wilmington 10/10 Excellent "Yes breakfast was Ok. Person running the room was excellent." [](https://expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Quality Inn Newark - Wilmington](//images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg) ### Quality Inn Newark - Wilmington 10/10 Excellent "Always come " [](https://expedia.ca/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information) ![Hyatt Place Wilmington Riverfront](//images.trvl-media.com/lodging/35000000/34930000/34927700/34927626/a064dc72_y.jpg) ### Hyatt Place Wilmington Riverfront 10/10 Excellent "In town for one night with family for a tournament. " [](https://expedia.ca/Wilmington-Hotels-Hyatt-Place-Wilmington-Riverfront.h34927626.Hotel-Information) ![Red Roof Inn PLUS+ Wilmington - Newark](//images.trvl-media.com/lodging/1000000/10000/7900/7845/aa58fe8d_y.jpg) ### Red Roof Inn PLUS+ Wilmington - Newark 10/10 Excellent "Clean room " [](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-PLUS-Wilmington-Newark.h7845.Hotel-Information) ![Sonesta ES Suites Wilmington - Newark](//images.trvl-media.com/lodging/1000000/20000/19100/19062/98de1f1c_y.jpg) ### Sonesta ES Suites Wilmington - Newark 10/10 Excellent "The room was beyond our expectations. It was very nice neat and clean. The staff were also very accommodating both check in and checking out staffwe enjoyed our stay and we look forward to rebooking for our girls night. " [](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.Hotel-Information) ![Embassy Suites by Hilton Newark Wilmington South](//images.trvl-media.com/lodging/1000000/330000/327600/327586/b7951f6a_y.jpg) ### Embassy Suites by Hilton Newark Wilmington South 10/10 Excellent "Very clean!! Nice room, great staff" [](https://expedia.ca/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information) ![Extended Stay America Suites Newark Christiana Wilmington](//images.trvl-media.com/lodging/1000000/120000/119100/119061/87ad8503_y.jpg) ### Extended Stay America Suites Newark Christiana Wilmington 10/10 Excellent "Good service " [](https://expedia.ca/Wilmington-Hotels-Extended-Stay-America-Suites-Newark-Christiana-Wilmington.h119061.Hotel-Information) ## Find out more about Chesapeake City ## Chesapeake City Cottages information | Number of reviews | 52 | | --- | --- | | Accommodation | 35 Cottages | | Lowest Price | CA $297 | | Highest Price | CA $669 | ## Frequently asked questions ### Why book your cottage in Chesapeake City with Expedia? > Booking a cottage in Chesapeake City is as easy as working out your travel dates and selecting your ideal place for a vacation in nature. From upmarket retreats to budget-friendly stays and cottages that include amenities like a kitchenette, Expedia has something for all traveler tastes. As for epic deals? We've got them too! ### How can I find cheap cottages in Chesapeake City? > With Expedia's filter tool, comparing cheap cottages in Chesapeake City is easy. To find properties that are friendly on the wallet, fine-tune your search results by budget, star rating and amenities. ### What is there to do in Chesapeake City near my cottage? > The perfect travel accessory is a well-planned schedule. 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