Title: Best Cottages in Shady Side in 2026 | Expedia.co.uk [Shady Side Travel Guide](https://expedia.co.uk/Shady-Side.dx6264943)[Hotels in Shady Side](https://expedia.co.uk/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Holiday Rentals in Shady Side](https://expedia.co.uk/Shady-Side-Holiday-Rentals.d6264943.Travel-Guide-HolidayRentals)[Shady Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Shady-Side.d6264943.Car-Hire-Guide)[Shady Side Holidays](https://expedia.co.uk/Shady-Side.d6264943.Holidays-City-Breaks) ![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__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 In two weeks [13 Mar - 15 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [24 Apr - 26 Apr](https://www.expedia.co.uk/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 three months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-06-19&endDate=2026-06-21&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) ![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) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w951h680x36y3-968871c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w1024h640x0y22-f248bc40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cozy Cottage in Historic Downtown [](https://www.expedia.co.uk/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.Hotel-Information) Historic District 9.6/10 Exceptional (16 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. £424 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16®ionId=6264943&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AA_SPRING_PROMO_6264943) ## Find holiday rentals that suit your style Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APARTMENT) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=HOUSE_BOAT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CONDO) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=COTTAGE) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VILLA) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Such a cool place to stay! Water pressure wasn’t great but it’s a very old building. " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Staff was outstanding room needed some Maintence Shower Door kept sliding open but everything else was 5 Star." [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Room was clean, warm and cozy. The cost was very reasonable so I wasn't expecting a suite! I wish I was staying longer. It will be my go to when I come to the area again!" [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 "Staff was beyond amazing and room was clean snd comfortable!" [](https://expedia.co.uk/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Rooms were clean, our request to have rooms close to each other was honored. Staff were very friendly. John, bartender at the restaurant was very accommodating to our gift exchange, DJ was fun and took requests. Front desk staff were friendly and helpful with our needs, checked that our rooms were ready when we arrived early even! Two of us live in this town, but we will be back for another staycation! " [](https://expedia.co.uk/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/faf6da25_y.jpg) ### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG 10/10 Excellent "Clean and staff is courteous and helpful" [](https://expedia.co.uk/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Friendly, clean" [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Great services" [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 10/10 Excellent "The room was clean the bed was so comfortable. The front desk and staff was so welcoming." [](https://expedia.co.uk/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ## Find out more about Shady Side ## Shady Side Cottages information | Number of reviews | 16 | | ----------------- | ----------- | | Accommodation | 76 Cottages | | Lowest Price | £424 | | Highest Price | £424 | ## 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 - More ways to book - [Book Cottages in Shady Side on Expedia.com ](https://www.expedia.com/Shady-Side-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation)