Title: Holiday Rentals Chestertown from £119: Find Short-Term Rentals & Holiday Accommodations | 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)[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 holiday rentals ![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/111000000/110560000/110553100/110553066/138fd4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/111000000/110560000/110553100/110553066/2d2dcf18.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 £369 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Baltimore-Hotels-5-Mi-To-Downtown-Baltimore-Quiet-Home-W-Porch.h110553066.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=2026-02-24&endDate=2026-02-25®ionId=7215&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## 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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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=2026-05-11&d1=2026-05-11&endDate=2026-05-14&d2=2026-05-14&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-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals) ## Top Chestertown Hotel Reviews ![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 "Staff was nice room was clean..." [](https://expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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) ![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 "It was a comfortable stay. " [](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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 "Rooms were great, but they were FREEZING. had the heater on all night and didn’t help at all. other than that the room was great!" [](https://expedia.co.uk/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Amazing location and staff!" [](https://expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 10/10 Excellent "Yes " [](https://expedia.co.uk/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.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 "Staff was great. Convenient location close to grocery and the harbor." [](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 service was good and the room was was clean " [](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.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 "Yes room was great" [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ## Find out more about Chestertown **Everything you need to know about** **Chestertown** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Chestertown holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chestertown holiday rentals we have selected for you start as low as £119 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Chestertown rentals** At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold ](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District ](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals ](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals ](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals ](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals ](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals ](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals ](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals ](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals ](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals ](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals ](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals ](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals ](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals ](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) ## Frequently asked questions ### Are there holiday rentals in Chestertown? ### What are some of the best holiday rentals that Chestertown has to offer? ### How many holiday rentals are there in Chestertown? ### What can I see and do in Chestertown? ### What are holiday rentals like in Chestertown? ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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