Title: 20 Best B&B in Chestertown, NY - Bed and Breakfast from $586 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d89045.Destination-Travel-Guides) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.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 Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown bed & breakfast ![Lake view](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, Hot Tub, Lake View (Birch) | Premium bedding, in-room safe, individually decorated](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/9867809e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/c74c01f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/ccbb7c0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Fern Lodge [](https://www.expedia.com/Lake-George-Hotels-The-Fern-Lodge.h1538972.Hotel-Information) Chestertown 10/10 Exceptional (52 reviews) "I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Morgan $527 nightly $586 total Mar 13 - Mar 14 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-The-Fern-Lodge.h1538972.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=2026-02-26&endDate=2026-02-27®ionId=89045&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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_89045) ![](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-Bed-And-Breakfast.d89045-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Bed-And-Breakfast.d89045-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg) ### Six Flags Great Escape Lodge & Indoor Waterpark 10/10 Excellent "Front desk staff upon arrival were great. The staff member I worked with helped us get a room upgrade for a small upcharge. Totally worth it. " [](https://expedia.com/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) ![Hampton Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/201ef456_y.jpg) ### Hampton Inn & Suites Lake George 10/10 Excellent "Everything stood out! This was honestly a very wonderful hotel experience for us, and we stay at a lot of hotels throughout the year. Highlights: Our room was spotless. The staff was incredibly nice. The breakfast offered a lot of variety. Our family really enjoyed the pool and hot tub as well." [](https://expedia.com/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information) ![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/a8530560_y.jpg) ### Fort William Henry Hotel and Conference Center 10/10 Excellent "Clean rooms, very courteous staff, beautiful property and fun environment " [](https://expedia.com/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information) ![Courtyard by Marriott Lake George](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191022/f47df569_y.jpg) ### Courtyard by Marriott Lake George 10/10 Excellent "Room was great, staff is great, second time at this hotel and it was consistent with the first stay!! Highly recommend" [](https://expedia.com/Lake-George-Hotels-Courtyard-By-Marriott-Lake-George.h15191022.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Lake George](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/4b0bd02a_y.jpg) ### La Quinta Inn & Suites by Wyndham Lake George 10/10 Excellent "Great staff and fun place for the kids. " [](https://expedia.com/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information) ![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/b0a450bb_y.jpg) ### Country Inn & Suites by Radisson, Lake George (Queensbury), NY 10/10 Excellent "The room was spotless" [](https://expedia.com/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information) ![Super 8 by Wyndham Lake George/Warrensburg Area](https://images.trvl-media.com/lodging/1000000/460000/459800/459792/a069ae03_y.jpg) ### Super 8 by Wyndham Lake George/Warrensburg Area 10/10 Excellent "Great spot" [](https://expedia.com/Lake-George-Hotels-Super-8-By-Wyndham-Lake-GeorgeWarrensburg-Area.h459792.Hotel-Information) ![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/c38b9040_y.jpg) ### The Queensbury Hotel 10/10 Excellent "Excellent " [](https://expedia.com/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information) ![Holiday Inn Resort Lake George - Adirondack Area by IHG](https://images.trvl-media.com/lodging/1000000/10000/1200/1178/3f808d49_y.jpg) ### Holiday Inn Resort Lake George - Adirondack Area by IHG 10/10 Excellent "Great relaxed vibe. Nice room and nice common places. " [](https://expedia.com/Lake-George-Hotels-Holiday-Inn-Lake-George-Turf.h1178.Hotel-Information) ## Find out more about Chestertown ## Chestertown B&B information | Number of reviews | 47 | | ----------------- | ----- | | Accommodation | 4 B&B | | Lowest Price | $586 | | Highest Price | $586 | ## Frequently asked questions ### What are the most popular Chestertown Bed & Breakfasts? ### What is the nightly rate for a Bed & Breakfast in Chestertown? ### When is the best time to book a B&B in Chestertown? > As the weather warms up, Chestertown comes alive with various festivals and events that celebrate local arts and culture. This is an excellent time for travelers who appreciate a vibrant community atmosphere and wish to experience the best of what the town has to offer, including farmers' markets and outdoor dining options. > > > For those looking for a more budget-friendly experience, November presents a wonderful opportunity to enjoy Chestertown in a quieter setting. During this month, you can witness the enchanting early signs of winter while taking leisurely strolls along the waterfront and enjoying the peaceful ambiance. The town's cozy charm shines through, making it a delightful choice for a relaxing getaway. ### What is the difference between a Chestertown Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Loon Lake Beach ](https://www.expedia.com/Loon-Lake-Beach-Hotels.0-l553248621554184980-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Brant Lake ](https://www.expedia.com/Brant-Lake-Cabins.d6347839-aaCabins.Travel-Guide-Accommodation) - [Resorts in Brant Lake ](https://www.expedia.com/Brant-Lake-Resorts.d6347839-aaResorts.Travel-Guide-Accommodation) - [B&B in Brant Lake ](https://www.expedia.com/Brant-Lake-Bed-And-Breakfast.d6347839-aaBedAndBreakfast.Travel-Guide-Accommodation) - [RV Parks in Brant Lake ](https://www.expedia.com/Brant-Lake-RV-Parks.d6347839-aaRVParks.Travel-Guide-Accommodation) - [Motels in Brant Lake ](https://www.expedia.com/Brant-Lake-Motels.d6347839-aaMotels.Travel-Guide-Accommodation) - 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