Title: Chester B&B: Find the Best Bed and Breakfast from CA $278 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d3000440455.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d3000440455.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d3000440455.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d3000440455.Destination-Travel-Guides) ![Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.](https://images.trvl-media.com/place/3000440455/ea96dd54-4b86-4885-83c9-585f6f8e1fb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Find a Bed and Breakfast in Chester from CA $278 - ![](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 [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000440455&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester B&B ![Lake](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/72010305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/8889a53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/f2afc3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Huntingfield Creek Rock Hall 10/10 Exceptional (56) "We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron [](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6594eb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 Deluxe Double, queen fire place](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6d7108e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Brooks House B&B St. Michaels 8.6/10 Excellent (65) "Gorgeous quaint historic house. Friendly owner, close to town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $252 CA $278 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d0af41e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/518088b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/ffb9b376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/18678d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront Easton 10/10 Exceptional (40) "This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $579 CA $637 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/8e209338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 2 Bedrooms, Balcony | Room amenity](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/23007304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/d05b07bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #2, King with Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/23402709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parsonage Inn St. Michaels 9.2/10 Wonderful (130) "Hosts were wonderful, breakfast was delicious, everything was walkable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaly CA $321 CA $353 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210325/d87a3375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Triple Room, Multiple Beds, Ensuite](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210325/9c7eb49a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210325/fab6537a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210325/e2305d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hummingbird Inn Easton 10/10 Exceptional (86) "The kindest most sweetest checkin" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole [](https://www.expedia.ca/Easton-Hotels-Hummingbird-Inn.h1210325.Hotel-Information) ![Horseback riding](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ed0e25a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/57a2b6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Bay View](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/aa3e4df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "Amazing, warm, gracious setting. Can’t wait to return " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/6c83d519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/w1857h2500x0y0-ac5cefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (81) "The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $267 CA $305 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.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=2025-12-12&endDate=2025-12-13®ionId=3000440455&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_3000440455) ![](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%2FChester-Bed-And-Breakfast.d3000440455-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Bed-And-Breakfast.d3000440455-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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 "The hotel was very clean, and staff was courteous and helpful " [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "The staff was excellent and friendly." [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Clean older rooms. Quite comfortable. Rick at the front desk was a superstar! Knowledgeable, and friendly. Great example for the younger staff. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "I have stayed several times over the last month or so totaling at leadt 7 nights and during every stay i have had a great experiene. Particularly with Chrissy who ive seen maonly during the night shift. Cannot understate how helpful and pleasant she has been. Probably the reason i wont stay anywhere else(if theres availability) in and around the Annapolis area. Keep up the amazing customer service!! 5 STARS " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Nice clean room. Good breakfast. Ample free parking." [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "The room was clean and the amenities were great! I loved the lobby and valet very fast and professional. I will stay here again. " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Location perfect " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Pretty good value. Good shower pressure, practically enough to pelt your skin off! Breakfast had a good variety, though the eggs were a strange texture. The waffle maker was nice. The hot tub was hot and fairly clean, though the jets were so forceful and chaotic it was kind of difficult to sit anywhere near them. Overall, good value" [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ## Find out more about Chester ## Chester B&B information | Number of reviews | 468 | | --- | --- | | Accommodation | 14 B&B | | Lowest Price | CA $278 | | Highest Price | CA $637 | ## Frequently asked questions ### Searching for B&Bs in Chester? > Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're traveling solo and hoping to get some local recommendations, a B&B can be a good choice for many different types of travelers. ### Are you thinking about a B&B instead of a traditional hotel? > With attentive service, an atmosphere suited to mingling with other guests, and of course a full breakfast to start the day, B&Bs all have a one-of-a-kind environment. ### What are the top B&Bs in Chester? > Here are some B&Bs in the area: [Flag House Inn](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information): 5 rooms. 10.6 mi (17 km) from the heart of Chester. Enjoy the local cuisine breakfast and unique décor. [George Brooks House B&B](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information): 6 rooms. 12.7 mi (20.5 km) from the downtown core. Enjoy the library and fireplace in the lobby. [Parsonage Inn](https://www.expedia.ca/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information): 8 rooms. Situated 13.3 mi (21.4 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. [The Oaks Waterfront](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information): 15 rooms. 17 mi (27.4 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. ### What's the best time of year to book my B&B in Chester? > When you're planning your stay in Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches. ### How can I get to and around Chester? > You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) from the city center. Otherwise, look for flights into Baltimore Washington Intl. Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Kent Island](https://www.expedia.ca/5Star-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Stevensville](https://www.expedia.ca/5Star-Stevensville-Hotels.s50-0-d162393.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Adults-Only-Resorts.0-n553248635976473602-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Boutique-Hotel.0-n553248635976473602-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Anchorage](https://www.expedia.ca/Anchorage-Annapolis-Hotels-Hotels-With-Hot-Tubs.0-n553248635976473602-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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