Title: Shady Side, MD Cottage Rentals from $624 | 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 In two weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side cottages ![Marina](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h447x0y118-8b5ab4ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/f5694e2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/afea8523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w950h680x38y3-96439ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cozy Cottage in Historic Downtown [](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) Historic District 9.6/10 Exceptional (19 reviews) "This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda Q. $547 nightly $624 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.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=2026-04-21&endDate=2026-04-22®ionId=6264943&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE) Houseboats [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=HOUSE_BOAT) Condos [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CONDO) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT) ![](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-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![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 "Excellent staff at Hotel" [](https://expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.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 2/10 Terrible "Extremely noisy!!!! Left the hotel that night" [](https://expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg) ### The Westin Annapolis 10/10 Excellent "Beautiful hotel. Great location. Friendly staff. " [](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![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 10/10 Excellent "I loved this property because it was in a secluded location and they allowed me to check in prior to three. the room was nice and the front desk staff were pleasant and offered me suggestions to visit the town." [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.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 "Fantastic accessibility to all shops" [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Hampton Inn & Suites Glenarden/Washington DC](https://images.trvl-media.com/lodging/20000000/19350000/19345400/19345309/e25a62d8_y.jpg) ### Hampton Inn & Suites Glenarden/Washington DC 10/10 Excellent "Great location, great hotel " [](https://expedia.com/College-Park-Hotels-Hampton-Inn-Suites-Glenarden.h19345309.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 "The food was good. The pool was nice. " [](https://expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 4/10 Poor "The kitchen staff very rude. The housekeeper never cleaned our room . " [](https://expedia.com/Upper-Marlboro-Hotels-Comfort-Inn.h19389.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 "It was ok for a nights rest. Didn’t even use the internet. Or the pool. Waffles were good. " [](https://expedia.com/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.Hotel-Information) ## Find out more about Shady Side ## Shady Side Cottages information | Number of reviews | 19 | | ----------------- | ----------- | | Accommodation | 76 Cottages | | Lowest Price | $624 | | Highest Price | $624 | ## Frequently asked questions ### How much do cottages in Shady Side cost? ### Why book your cottage in Shady Side with Expedia? ### How can I find cheap cottages in Shady Side? ### What is there to do in Shady Side near my cottage? ## 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) - 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