--- title: "20 Best B&B in Chesapeake Beach, MD - Bed and Breakfast from $153 | Expedia" description: "Travel the World Better - with a Bed and Breakfast in Chesapeake Beach! Read reviews, search by map, and rent your dream B&B in Chesapeake Beach with Expedia." canonical: "https://www.expedia.com/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation" language: en-US market: US currency: USD prices_as_of: 2026-11-14T21:39:20Z --- Plan your trip - [Chesapeake Beach Travel Guide](https://www.expedia.com/Chesapeake-Beach.dx88967) - [Hotels in Chesapeake Beach](https://www.expedia.com/Chesapeake-Beach-Hotels.d88967.Travel-Guide-Hotels) - [Flights to Chesapeake Beach](https://www.expedia.com/Cheap-Flights-To-Chesapeake-Beach.d88967.Travel-Guide-Flights) - [Things to do in Chesapeake Beach](https://www.expedia.com/Things-To-Do-In-Chesapeake-Beach.d88967.Travel-Guide-Activities) - [Car Rentals in Chesapeake Beach](https://www.expedia.com/Car-Rentals-In-Chesapeake-Beach.d88967.Car-Rental-Guide) - [Chesapeake Beach Vacation Packages](https://www.expedia.com/Chesapeake-Beach.d88967.Destination-Travel-Guides) - [Vacation Rentals in Chesapeake Beach](https://www.expedia.com/Chesapeake-Beach-Vacation-Rentals.d88967.Travel-Guide-VacationRentals) # Book Chesapeake Beach Bed & Breakfast ![A coastal town with a marina, residential buildings, and a clear sky.](https://images.trvl-media.com/place/88967/88834884-dfa0-472f-8984-918630335b80.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals ### OneKeyCash Earn OneKeyCash on all your eligible bookings ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates [Check prices for these dates, December 14 – 15, 2026](https://www.expedia.com/Hotel-Search?regionId=88967&startDate=2026-12-14&endDate=2026-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&lodging=BED%5FAND%5FBREAKFAST) [View in a map](https://www.expedia.com/Hotel-Search?regionId=88967&stayLength=1&daysInFuture=30&pwaOverlay=map) ## Our top choices for Chesapeake Beach bed & breakfast ### [1\. The Inn at Tacaro Estate](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![A hot tub in a grassy area with a building in the background.](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Tracys Landing - Guest rating: 9.6/10 (Exceptional, 20 reviews) - Price: $358 nightly, $408 total, Dec 15 - Dec 16, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast - Review: The owners are very friendly and accommodating. Relaxing getaway, by kristine ### [2\. Historic 1825 Chesapeake Farm Stay](https://www.expedia.com/St-Leonard-Hotels-Historic-1825-Chesapeake-Farm-Stay.h133935842.Hotel-Information) ![A garden with raised beds and a wooden fence.](https://images.trvl-media.com/lodging/134000000/133940000/133935900/133935842/61938285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: St. Leonard - Guest rating: 10/10 (Exceptional, 6 reviews) - Price: $138 nightly, $153 total, Dec 11 - Dec 12, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast - Review: was a very good experience the house was super cute and very clean the bed was comfy, by Robert ### [3\. Laurel Grove Inn on the South](https://www.expedia.com/Annapolis-Hotels-Laurel-Grove-Inn-On-The-South.h2472717.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/3000000/2480000/2472800/2472717/d8d9c9e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Annapolis - Guest rating: 9.4/10 (Exceptional, 536 reviews) - Price: $180 nightly, $205 total, Dec 14 - Dec 15, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast - Review: I stayed here with my daughter the night before a lacrosse tournament at the Naval Academy. Beautiful property, excellent host. I will definitely stay here again! Thank you!, by Michael ### [4\. Parsonage Inn](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/8e209338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Downtown St. Michaels - Guest rating: 9.2/10 (Wonderful, 139 reviews) - Price: $250 nightly, $275 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast - Review: The staff were great. The breakfast was delicious and the location is perfect for walking into town., by Susan ### [5\. Carib Comfort B and B](https://www.expedia.com/Upper-Marlboro-Hotels-Carib-Comfort-B-And-B.h136952769.Hotel-Information) ![An outdoor patio with seating, a table, and a blue umbrella.](https://images.trvl-media.com/lodging/137000000/136960000/136952800/136952769/4aec2b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: Upper Marlboro - Price: $194 nightly, $219 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast ### [6\. George Brooks House B&B](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![A two-story house with a swimming pool, outdoor seating, and a covered patio area.](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Location: St. Michaels - Guest rating: 8.8/10 (Excellent, 78 reviews) - Price: $199 nightly, $219 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Chesapeake Beach bed & breakfast - Review: This weekend was an anniversary gift for my daughter and her husband. They had a wonderful time and were highly complimentary of the accommodations, the delicious breakfast and the location., by Erin 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://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=88967&adults=2&lodging=BED%5FAND%5FBREAKFAST&sort=RECOMMENDED&openPlayBack=true) ## Learn more about Chesapeake Beach Stroll the half-mile boardwalk at sunset, where fishing boats return with the day's catch and locals gather for crab feasts. Families splash in the water park's eight slides by day, then hunt for fossilized shark teeth along the Bay's ancient shoreline. [See all hotels in Chesapeake Beach](https://www.expedia.com/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29&adults=2®ionId=88967) ![A coastal town with a marina, residential buildings, and a clear sky.](https://images.trvl-media.com/place/88967/88834884-dfa0-472f-8984-918630335b80.jpg?impolicy=fcrop&w=900&h=263&p=1&q=high) ## Top reviews in Chesapeake Beach ### [The Inn at Tacaro Estate](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![A hot tub in a grassy area with a building in the background.](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 6220 Town Point Rd, Tracys Landing, MD, 20779, US - Location: Tracys Landing - Star rating: 5/5 - Guest rating: 9.6/10 (20 reviews) - Review: It was a spectacular location, beautiful rooms and restoration of a stunning property, the owners Luciano and Susan are superstars, the staff amazing the breakfast was unbelievably and the ambiance was amazing! I was in Maryland for a wedding, I never thought I would return but I MUST come back and stay again!, by ian, October 10, 2026, rated 10/10 Excellent ### [Historic 1825 Chesapeake Farm Stay](https://www.expedia.com/St-Leonard-Hotels-Historic-1825-Chesapeake-Farm-Stay.h133935842.Hotel-Information) ![A garden with raised beds and a wooden fence.](https://images.trvl-media.com/lodging/134000000/133940000/133935900/133935842/61938285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1380 Wagner Street, St. Leonard, MD, 20685, US - Location: St. Leonard - Star rating: 2/5 - Guest rating: 10/10 (6 reviews) - Review: was a very good experience the house was super cute and very clean the bed was comfy, by Robert, November 10, 2026, rated 10/10 Excellent ### [Laurel Grove Inn on the South](https://www.expedia.com/Annapolis-Hotels-Laurel-Grove-Inn-On-The-South.h2472717.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/3000000/2480000/2472800/2472717/d8d9c9e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 2881 South Have Road, Annapolis, MD, 21401, US - Location: Annapolis - Star rating: 3.5/5 - Guest rating: 9.4/10 (536 reviews) - Review: We really loved everything, but Guinness the dog topped everything. There was a miscommunication about dinner reseservations but it worked out. Would have appreciated more whole food at breakfast. Neither of these would keep me away. In fact, we would love to see the property in the spring., by Marti, November 22, 2015, rated 10/10 Excellent ### [Parsonage Inn](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/8e209338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 210 North Talbot Street, St. Michaels, MD, 21663, US - Location: Downtown St. Michaels - Star rating: 3.5/5 - Guest rating: 9.2/10 (139 reviews) - Review: We didn't have any plans for Spring Break, but the weather was fantastic and we decided to go to St. Michaels to go kayaking. Found the Parsonage online and got a great suite for ourselves and our son at the last minute. Way comfortable and LOVED how close to everything in town it was. Enjoyed relaxing evenings watching movies from the DVD collection. Great parking for our truck., by D, April 13, 2017, rated 10/10 Excellent ### [George Brooks House B&B](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![A two-story house with a swimming pool, outdoor seating, and a covered patio area.](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 24500 Rolles Range Road, St. Michaels, MD, 21663, US - Location: St. Michaels - Star rating: 3/5 - Guest rating: 8.8/10 (78 reviews) - Review: Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse..., by Anonymous traveler, July 22, 2019, rated 10/10 Excellent ## Frequently Asked Questions ### What is the nightly rate for a Bed and Breakfast in Chesapeake Beach? Prices for B&Bs in Chesapeake Beach often vary, but you can find a great deal from $153 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesapeake Beach B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high. ### When is the best time to book a Bed and Breakfast in Chesapeake Beach? The most popular time to book a B&B in Chesapeake Beach is during the summer months, particularly from June to August. This peak season is characterized by warm weather, with temperatures typically ranging from the mid-70s to the low 90s Fahrenheit, making it ideal for beachgoers and families seeking fun in the sun. Visitors flock to the area to enjoy water activities, such as swimming, kayaking, and fishing, while also partaking in the vibrant local culture, including festivals and outdoor concerts. July stands out as the most favored month, offering a bustling atmosphere filled with fellow travelers eager to soak up the sun. During this time, you can take advantage of a variety of events, from art shows to live music performances, all set against the backdrop of the beautiful Chesapeake Bay. If you're looking for a more budget-friendly option, consider visiting in the shoulder months of late spring or early fall. September, in particular, offers pleasant weather and fewer crowds, allowing for a more relaxed experience. You can enjoy scenic walks along the beach, explore local shops, and indulge in the region’s renowned seafood without the hustle and bustle of peak season. ### What is the difference between a Chesapeake Beach Bed & Breakfast and a hotel? Every Chesapeake Beach B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesapeake Beach B&Bs. ## Explore a world of travel with Expedia - [Lodging](?equalTargetTab=tab-0) - [Flights](?equalTargetTab=tab-1) - [Packages](?equalTargetTab=tab-2) - [Cars](?equalTargetTab=tab-3) - [Things to Do](?equalTargetTab=tab-4) - [Cottages in Anne Arundel County](https://www.expedia.com/Anne-Arundel-County-Cottages.d553248635083910990-aaCottages.Travel-Guide-Accommodation) - [Bethesda Hotels](https://www.expedia.com/Bethesda-Hotels.d6057493.Travel-Guide-Hotels) - [Condo Rentals in Deale Beach](https://www.expedia.com/Deale-Beach-Condos.d553248635975876712-aaCondos.Travel-Guide-Accommodation) - [Ryokans in Annapolis](https://www.expedia.com/Annapolis-Ryokans.d6034082-aaRyokans.Travel-Guide-Accommodation) - [Cabin Rentals in Chesapeake Beach](https://www.expedia.com/Chesapeake-Beach-Cabins.d88967-aaCabins.Travel-Guide-Accommodation) - [Motels in Friendship](https://www.expedia.com/Friendship-Motels.d3000440601-aaMotels.Travel-Guide-Accommodation) - 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Thurgood Marshall airport](https://www.expedia.com/Car-Rentals-In-Baltimore-Washington-Intl-Thurgood-Marshall.d4806466.Car-Rental-Guide) - [Car rentals near Maryland](https://www.expedia.com/Destinations-In-Maryland.d222.Car-Rental-Destinations) - [Things to do in Maryland](https://www.expedia.com/Things-To-Do-In-Maryland.d222.Travel-Guide-Activities) - [Things to do in Chesapeake Beach](https://www.expedia.com/Things-To-Do-In-Chesapeake-Beach.d88967.Travel-Guide-Activities) - [Things to do in Annapolis](https://www.expedia.com/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities) ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation en-PH: https://www.expedia.com.ph/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation es: https://www.expedia.com/es/Chesapeake-Beach-Bed-And-Breakfasts.d88967-aaBedAndBreakfasts.Guia-Viajes-Alojamiento en-CA: https://www.expedia.ca/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation en-AU: https://www.expedia.com.au/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation ja-JP: https://www.expedia.co.jp/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation zh-CN: https://www.expedia.com/cn/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation en-US: https://www.expedia.com/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation en-SG: https://www.expedia.com.sg/Chesapeake-Beach-Bed-And-Breakfast.d88967-aaBedAndBreakfast.Travel-Guide-Accommodation ```