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 [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 weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-05-29&endDate=2026-05-31&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) ![Free breakfast](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.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) ### 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) "A beautiful renovated historical house with charm, clean rooms, decorative furnishings and a wonderful hot breakfast. What we enjoyed the most was the warm hospitality of Willard, Valerie, and the other staff. Very close to downtown St. Michael’s, but just far enough away to give a nice feel of natural serenity. Great for a quick getaway from the city. We will be back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles $170 nightly $187 total Apr 2 - Apr 3 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) ![Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e07c03ef.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) ### 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 Apr 2 - Apr 3 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) ![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) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.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) ### Flag House Inn [](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District 9.2/10 Wonderful (91 reviews) "The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard $182 nightly $207 total Apr 5 - Apr 6 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) ![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) ![Interior](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/5726b171.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 $286 nightly $326 total Apr 5 - Apr 6 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 Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/121000000/120990000/120988400/120988327/c937676d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/121000000/120990000/120988400/120988327/da75fa72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors, printers](https://images.trvl-media.com/lodging/121000000/120990000/120988400/120988327/2d625e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120990000/120988400/120988327/0a2051d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Luxury 8BR Family Retreat Near DC - Perfect for Groups & Families [](https://www.expedia.com/Glenn-Dale-Hotels-Spacious-Luxury-8BR-Family-Retreat-Near-DC-Perfect-For-Groups-Families.h120988327.Hotel-Information) Glenn Dale 8.0/10 Very Good (2 reviews) "Easy to find, easy to get in, spacious " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler $948 nightly $1,071 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Glenn-Dale-Hotels-Spacious-Luxury-8BR-Family-Retreat-Near-DC-Perfect-For-Groups-Families.h120988327.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/126000000/125430000/125420600/125420511/3f712ced.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 $591 nightly $668 total Apr 20 - Apr 21 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=2026-04-15&endDate=2026-04-16®ionId=6264943&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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 Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 6/10 Okay "It was a very nice area. The staff were super nice and welcoming. Rooms was okay but definitely needs an update but it’s still good. We had a proble with the sink and maintenance came and fixed it right away. " [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![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 "Great location " [](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Very clean. Attentive and helpful staff " [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely. " [](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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 "the property was clean and overall Ok. Few things in the building seemed dated but nothing that caused issues or concerns" [](https://expedia.com/Upper-Marlboro-Hotels-Comfort-Inn.h19389.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 "Cool staff" [](https://expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.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 8/10 Good "The rooms are very comfortable and the hotel near a mall with a cinema multiplex. The night we stayed thete were groups of students that rose at 4 am on Monday morning making the corridor on the 2nd floor a bit noisy school break on calendar)." [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Had a great stay. The bed was comfortable, room was clean and spacious, and the property is well located and quiet with a woodsy atmosphere. I had breakfast and enjoyed the waffle maker though the eggs were not great. Wish there had been some fruit to add to the waffles. " [](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 "The room was clean and comfortable. The hotel was decorated with a fun nautical theme. The location is excellent and close to dining and shopping. " [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ## Find out more about Shady Side ## Shady Side B&B information | Number of reviews | 335 | | ----------------- | ------ | | Accommodation | 16 B&B | | Lowest Price | $164 | | Highest Price | $1,071 | ## 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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