Title: Shady Side B&B: Find the Best Bed and Breakfast from CA $245 | Expedia.ca [Hotels in Shady Side](https://expedia.ca/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.ca/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.ca/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Shady Side Car Rentals](https://expedia.ca/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.ca/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) # Find a Bed and Breakfast in Shady Side from CA $245 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shady Side B&B ![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](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/aeffd976.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 (64) "Gorgeous quaint historic house. Friendly owner, close to town " CA $277 CA $305 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/40000000/39530000/39529200/39529191/96bfef96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/40000000/39530000/39529200/39529191/45038f0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/40000000/39530000/39529200/39529191/256bb61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/40000000/39530000/39529200/39529191/389e51ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Horn Point Eastport 9.6/10 Exceptional (21) "Family owned with care and pride. Excellent food and recommendations for other restaurants and activities. " CA $482 CA $549 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Annapolis-Hotels-Inn-At-Horn-Point.h39529191.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) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/3e21912d.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/518088b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront Easton 10/10 Exceptional (38) "Loved the Oaks! Fabulous accommodations and excellent staff" CA $579 CA $636 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Full-size fridge, blender, toaster oven, waffle maker](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/1eac847e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Garden View | Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/c6a32c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/90332b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | In-room dining](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/49f997cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Villa Upper Marlboro CA $236 CA $266 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.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) ![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) ![Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e07c03ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parsonage Inn St. Michaels 9.2/10 Wonderful (130) "Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!" CA $321 CA $353 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111700000/111698900/111698847/cae7de91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111700000/111698900/111698847/dfae5bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, bidet, towels, soap](https://images.trvl-media.com/lodging/112000000/111700000/111698900/111698847/7814dd52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/112000000/111700000/111698900/111698847/667ac63e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern 1BR Near DC – Quiet Comfort, Fast Commute District Heights 10/10 Exceptional (4) "I thoroughly enjoyed my stay. Poo" CA $133 CA $245 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/District-Heights-Hotels-14-Miles-To-Natl-Mall-District-Heights-Retreat.h111698847.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) ![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) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (79) "Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!" CA $329 CA $375 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.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) ![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) ![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](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "Amazing hospitality " CA $568 CA $648 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.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=2025-10-26&endDate=2025-10-27®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.ca/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.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Bed-And-Breakfast.d6264943-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway](//images.trvl-media.com/lodging/1000000/10000/6400/6366/b2f3a1ba_y.jpg) ### La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 10/10 Excellent "Great clean room. Everything worked. Thank you." [](https://expedia.ca/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.Hotel-Information) ![Microtel Inn & Suites by Wyndham Gambrills](//images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg) ### Microtel Inn & Suites by Wyndham Gambrills 10/10 Excellent "Much thanks " [](https://expedia.ca/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent " Very clean and fresh room The TV screen already had my name on it !" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Comfort Inn Largo-Washington DC East](//images.trvl-media.com/lodging/1000000/20000/19400/19389/428ef9f4_y.jpg) ### Comfort Inn Largo-Washington DC East 10/10 Excellent "The staff were awesome very respectful, helpful etc. and my room was clean. This is my favorite place to stay. Shoutout to the sales department and the DM. Keep up the great work see y’all soon. " [](https://expedia.ca/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were uniformly attentive and friendly." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Spacious room, very clean and comfortable lots of eclectic nautical furniture. We did not have breakfast. Easy parking in and out right in the heart of restaurants, & bars and a short walk to the harbor." [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![DoubleTree by Hilton Hotel Largo/Washington DC](//images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 10/10 Excellent "So comfortable for me and my kids. " [](https://expedia.ca/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Room was clean, Staff was very friendly and welcoming. " [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Comfort Inn Conference Center](//images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921_y.jpg) ### Comfort Inn Conference Center 10/10 Excellent "Very clean, easy check in (checked in around 11:30pm), quiet, and excellent breakfast " [](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ## Find out more about Shady Side ## Shady Side B&B information | Number of reviews | 346 | | --- | --- | | Accommodation | 12 B&B | | Lowest Price | CA $245 | | Highest Price | CA $648 | ## Frequently asked questions ### Searching for B&Bs in Shady Side? > If you're looking for something a little different than the traditional hotel experience, a bed and breakfast might be the perfect option for your vacation. If your ideal vacation to Shady Side includes spending lots of time outside, Shadyside Park is a good spot to enjoy the scenery. ### Are you thinking about B&Bs over traditional hotel rooms? > With attentive service, opportunities to meet guests from other places, and of course a full breakfast to start the day, B&Bs provide a unique environment. ### What are the best B&Bs in Shady Side? > Here are some B&Bs in the surrounding area: [Laurel Grove Inn on the South](https://www.expedia.ca/Annapolis-Hotels-Laurel-Grove-Inn-On-The-South.h2472717.Hotel-Information): 5 rooms. 9.2 mi (14.8 km) from the heart of Shady Side. Enjoy the deli and arcade game room. [George Brooks House B&B](https://www.expedia.ca/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information): 6 rooms. 15.6 mi (25.1 km) from the downtown core. Enjoy the library and fireplace in the lobby. [Legacy Villa](https://www.expedia.ca/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.Hotel-Information): 2 rooms. 14.9 mi (24 km) from the heart of downtown. Enjoy the in-room pools and massage services. [Inn at Horn Point](https://www.expedia.ca/Annapolis-Hotels-Inn-At-Horn-Point.h39529191.Hotel-Information): 3 rooms. Located 8.8 mi (14.2 km) from the core of Shady Side. Enjoy the massage services and private yard. ### What's the best time of year to book my B&B in Shady Side? > When you're dreaming of a getaway to Shady Side, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches. ### What is there to do in Shady Side? > When you want to explore some things to do in town, Shadyside Park and Captain Avery Museum are some notable sights to visit. You might check out Franklin Point State Park if you have time to see more of the area. ### How can I get to and around Shady Side? > Planning your excursions in and around Shady Side is easier with these transportation options. Fly into Fort Meade, MD (FME-Tipton), which is located 21.6 mi (34.8 km) away from the heart of the city. Otherwise, you can search for flights to College Park, MD (CGS), which is 24.1 mi (38.7 km) away. 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