Title: 20 Best B&B in Shady Side, MD - Bed and Breakfast from $164 | 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) - ![](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 [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) ![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) ![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) ![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 (70 reviews) "Gorgeous quaint historic house. Friendly owner, close to town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $160 nightly $176 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) ![Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e07c03ef.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) ### 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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.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 $300 nightly $343 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) ![Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/c5479a6f.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 $489 nightly $538 total Mar 15 - Mar 16 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) ![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) ![Interior](https://images.trvl-media.com/lodging/126000000/125430000/125420600/125420511/3f712ced.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=2026-03-27&endDate=2026-03-28®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 ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Fantastic location! Great beds! Absolute gem " [](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "This was a great location for everything from the town circles to the waterfront. Great restaurants all closeby. Only issue was the elevator wasn't working at that time." [](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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 6/10 Okay "Room was clean" [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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 6/10 Okay "The floors were not cleaned at all in the room we stayed. They were very strict and dirty. Where the coffee tray was was also very sticky underneath. It was clear the room was only cleaned around areas and not actually throughly cleaned. " [](https://expedia.com/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.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 "Everything was great 👍 " [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Holiday Inn Express I-95 Capitol Beltway-Largo by IHG](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/fb2063de_y.jpg) ### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG 10/10 Excellent "Clean, quiet and very comfortable. Staff was super friendly. Enjoyed our stay." [](https://expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.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 "The place was amazing.I will not stay anywhere else when I get to annapolis.I stay there probably five or six times out of the year" [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 8/10 Good "Central l9cation, easy walk to all sites." [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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 10/10 Excellent "We often stay here when in town. We have always found the staff to be professional and customer focused and the property tidy and welcoming. Breakfast could be better but there are other options in a stones throw if you desire a more hearty breakfast." [](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 | 329 | | ----------------- | ------ | | Accommodation | 16 B&B | | Lowest Price | $164 | | 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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