Title: 20 Best B&B in Shady Side, MD - Bed and Breakfast from $158 | Expedia.com [Shady Side Travel Guide](https://expedia.com/Shady-Side.dx6264943)[Hotels in Shady Side](https://expedia.com/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.com/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.com/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Car Rentals in Shady Side](https://expedia.com/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.com/Shady-Side.d6264943.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-27&endDate=2026-03-29&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side bed & breakfast ![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Luxury Double, King Jacuzzi with fireplace | Premium bedding, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/aeffd976.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/1e71523a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Brooks House B&B [](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) St. Michaels 8.8/10 Excellent (69 reviews) "Gorgeous quaint historic house. Friendly owner, close to town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $144 nightly $158 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.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) ![Room #6, Queen with Bathtub | Egyptian cotton sheets, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e0611706.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) ### Parsonage Inn [](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) Downtown St. Michaels 9.2/10 Wonderful (131 reviews) "Hosts were wonderful, breakfast was delicious, everything was walkable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaly $149 nightly $164 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar](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 [](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District 9.4/10 Exceptional (87 reviews) "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 $182 nightly $207 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/b1c929dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/5726b171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/d7ca8491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate [](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Tracys Landing 9.4/10 Exceptional (12 reviews) "Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend \*\*\*\*\*" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd $303 nightly $346 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/6aa17d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom, Balcony | Balcony view](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/1f0e0a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront [](https://www.expedia.com/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Easton 10/10 Exceptional (41 reviews) "Staff, breakfast, and room were all superb!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey $440 nightly $484 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/126000000/125430000/125420600/125420511/w1024h751x0y7-7c73b145.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125430000/125420600/125420511/f125cdb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125430000/125420600/125420511/158481f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/126000000/125430000/125420600/125420511/28de18e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 5BR Retreat Near DC with Private Gym - Perfect for Group Getaway [](https://www.expedia.com/Glenn-Dale-Hotels-Spacious-5BR-Retreat-Near-DC-With-Private-Gym-Perfect-For-Group-Getaway.h125420511.Hotel-Information) Glenn Dale $620 nightly $700 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Glenn-Dale-Hotels-Spacious-5BR-Retreat-Near-DC-With-Private-Gym-Perfect-For-Group-Getaway.h125420511.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=2026-03-26&endDate=2026-03-27®ionId=6264943&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_6264943) ![](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%2FShady-Side-Bed-And-Breakfast.d6264943-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Bed-And-Breakfast.d6264943-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 6/10 Okay "Didn’t use anything. Ice machine was broken on our floor." [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Comfort Inn Conference Center](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/c88d625f_y.jpg) ### Comfort Inn Conference Center 4/10 Poor "Nice location" [](https://expedia.com/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Great customer service " [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Every stay is excellent " [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway](https://images.trvl-media.com/lodging/1000000/10000/6400/6366/c4bcae00_y.jpg) ### La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 8/10 Good "Great service " [](https://expedia.com/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.Hotel-Information) ![Comfort Inn Largo-Washington DC East](https://images.trvl-media.com/lodging/1000000/20000/19400/19389/428ef9f4_y.jpg) ### Comfort Inn Largo-Washington DC East 10/10 Excellent "Nice overnight stay for an NFL game" [](https://expedia.com/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Big room, friendly staff, great food at the restaurant, and perfect location " [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Clean, friendly staff and great area" [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Microtel Inn & Suites by Wyndham Gambrills](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg) ### Microtel Inn & Suites by Wyndham Gambrills 8/10 Good "Didn't use laundry service, however dryer was out of service. Room was nice. Used the exercise room, surprised there were no cleaning products in the room to clean equipment after use :( ." [](https://expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ## Find out more about Shady Side ## Shady Side B&B information | Number of reviews | 328 | | ----------------- | ------ | | Accommodation | 16 B&B | | Lowest Price | $158 | | Highest Price | $700 | ## Frequently asked questions ### What is the nightly rate for a B&B in Shady Side? ### When is the best time to book a B&B in Shady Side? > April typically sees mild temperatures ranging from the mid-50s to low 70s Fahrenheit, which is superb for leisurely strolls along the shoreline or visiting local parks. As the season progresses into May and June, the warmth invites a lively atmosphere, with various festivals and events that showcase the local culture and community spirit. > > > For those looking for a more budget-friendly option, consider visiting in December. While the weather is cooler, with temperatures averaging in the low 30s to mid-40s Fahrenheit, the holiday season brings a unique charm to Shady Side. You can enjoy festive decorations, cozy gatherings, and a peaceful ambiance that allows for reflective exploration of the area. ### What is the difference between a Shady Side Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Shadyside Park ](https://www.expedia.com/Shadyside-Park-Hotels.0-l6263308-0.Travel-Guide-Filter-Hotels) - [Hotels near Captain Avery Museum ](https://www.expedia.com/Captain-Avery-Museum-Hotels.0-l6263322-0.Travel-Guide-Filter-Hotels) - [B&B in Galesville ](https://www.expedia.com/Galesville-Bed-And-Breakfast.d6264947-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Galesville ](https://www.expedia.com/Galesville-Motels.d6264947-aaMotels.Travel-Guide-Accommodation) - [Galesville Hotels ](https://www.expedia.com/Galesville-Hotels.d6264947.Travel-Guide-Hotels) - [3 Star Hotels in Galesville ](https://www.expedia.com/3Star-Galesville-Hotels.s30-0-d6264947.Travel-Guide-Filter-Hotels) - 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