Title: Shady Side Cottages from CA $381 | 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) # Search Shady Side Cottage Rentals from CA $381 - ![](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 In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=COTTAGE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shady Side Cottages ![Property grounds](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/a75bb6ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/488be20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/10bef897.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/72000000/71120000/71116900/71116837/117e79aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Owings 10/10 Exceptional (48) "We love this place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan K. CA $178 CA $381 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Close-To-North-Chesapeake-Beach.h71116837.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/w1179h1552x0y10-4ae4c675.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/6b784e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/d32606e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114310000/114310000/114309947/a52717e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in North Beach 10/10 Exceptional (1) "Great location! Everything was on hand and it was an easy sweet little cottage to be in.It was clean and very functional with the added bonus of being so close to all the activity in North Beach.Heather was responsive and obviously cares about her guests and their stay.Highly recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgina P. CA $180 CA $390 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/North-Beach-Hotels-Charming-2-Bedroom-1-Bath-Cottage-With-AC.h114309947.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/115000000/114590000/114588600/114588502/938d7ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/115000000/114590000/114588600/114588502/66cb2e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114590000/114588600/114588502/23711e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/115000000/114590000/114588600/114588502/639bccd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Saint Michaels 10/10 Exceptional (1) CA $367 CA $541 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/St-Michaels-Hotels-2-Egret-Cottage-Harris-Cove.h114588502.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/fa37e440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/37ea1a39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/3508a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108010000/108008600/108008595/d98176c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Stevensville 10/10 Exceptional (6) "Beautiful home. Very nice and quiet neighborhood on the water. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shannan t. CA $563 CA $1,233 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Stevensville-Hotels-Charming-2-Bedroom-Waterfront-Cottage-In-Peaceful-Stevensville-With-AC.h108008595.Hotel-Information) ![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) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w707h678x157y5-ccae639e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w905h683x60y0-0737769d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Historic District 9.6/10 Exceptional (15) "We had a very lovely stay . This is an excellent location . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. CA $635 CA $1,056 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-12-08&endDate=2025-12-09®ionId=6264943&adults=2&lodging=COTTAGE&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6264943) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=VACATION_HOME) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=COTTAGE) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=HOUSE_BOAT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=VILLA) Condos [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=CONDO) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-21&d1=2026-02-21&endDate=2026-02-24&d2=2026-02-24&lodging=CABIN) ![](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-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Cottages.d6264943-aaCottages.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/aa92a5c8_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 10/10 Excellent "Everything was wonderful" [](https://expedia.ca/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/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Everything was great" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Hampton Inn & Suites Glenarden/Washington DC](https://images.trvl-media.com/lodging/20000000/19350000/19345400/19345309/114260b9_y.jpg) ### Hampton Inn & Suites Glenarden/Washington DC 10/10 Excellent "Nice modern room. Clean. Wonderful late night front desk staff. My only complaint was the hot water wasn’t very hot. " [](https://expedia.ca/College-Park-Hotels-Hampton-Inn-Suites-Glenarden.h19345309.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 "Everything Was Excellent I Have No Complaints." [](https://expedia.ca/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) ![Hampton Inn & Suites Annapolis](https://images.trvl-media.com/lodging/1000000/70000/64200/64115/23865424_y.jpg) ### Hampton Inn & Suites Annapolis 10/10 Excellent "The courtesy of the staff. " [](https://expedia.ca/Annapolis-Hotels-Hampton-Inn-Suites-Annapolis.h64115.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 "Always a great stay!!!" [](https://expedia.ca/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "." [](https://expedia.ca/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 "I was very happy with this hotel. It is in a great walkable area. The staff were super friendly and helpful. The valet was efficiently done by app. We found ourselves commenting throughout that it was better than we expected. " [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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 "Very good clean rooms location and comfortable " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ## Find out more about Shady Side ## Shady Side Cottages information | Number of reviews | 64 | | --- | --- | | Accommodation | 67 Cottages | | Lowest Price | CA $381 | | Highest Price | CA $1,233 | ## Frequently asked questions ### How much do cottages in Shady Side cost? > Cottages in Shady Side range between CA $381 and CA $1,233 per night. These retreats offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### Why book your cottage in Shady Side with Expedia? > Reserving a cottage in Shady Side is as simple as deciding on your travel dates and choosing your ideal place for a getaway in nature. From upscale retreats to affordable stays and cottages that include perks like a pool, Expedia has something for all styles. As for epic deals? We've got them as well! ### How can I find cheap cottages in Shady Side? > Expedia is here to help you locate cheap cottages in Shady Side. To book a fantastic stay in a few quick clicks, use our handy filter tool to refine your search results by amenities, star rating and budget. ### What is there to do in Shady Side near my cottage? > If you're ready to discover the best of Shady Side, find your way to [Shadyside Park](https://www.expedia.ca/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction). 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[Rose Haven Hotels](https://www.expedia.ca/Rose-Haven-Hotels.d153066.Travel-Guide-Hotels) - [Inns in Rose Haven](https://www.expedia.ca/Rose-Haven-Inns.d153066-aaInns.Travel-Guide-Accommodation) - [Aparthotels in Selby-on-the-Bay](https://www.expedia.ca/Selby-On-The-Bay-Apart-Hotels.d553248634999271692-aaApartHotels.Travel-Guide-Accommodation) - [Selby-On-The-Bay Hotels](https://www.expedia.ca/Selby-On-The-Bay-Hotels.d553248634999271692.Travel-Guide-Hotels) - [Aparthotels in Tracys Landing](https://www.expedia.ca/Tracys-Landing-Apart-Hotels.d3000440927-aaApartHotels.Travel-Guide-Accommodation) - [Tracys Landing Hotels](https://www.expedia.ca/Tracys-Landing-Hotels.d3000440927.Travel-Guide-Hotels) - [Motels in Tracys Landing](https://www.expedia.ca/Tracys-Landing-Motels.d3000440927-aaMotels.Travel-Guide-Accommodation) - [West River Hotels](https://www.expedia.ca/West-River-Hotels.d553248635975860906.Travel-Guide-Hotels) - [Flights to Deale](https://www.expedia.ca/Cheap-Flights-To-Deale.d55664.Travel-Guide-Flights) - [Flights to Edgewater](https://www.expedia.ca/Cheap-Flights-To-Edgewater.d6348965.Travel-Guide-Flights) - [Flights from Allentown (ABE) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/abe/anp/allentown-to-annapolis) - [Flights from Buffalo (BUF) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/buf/anp/buffalo-to-annapolis) - [Flights from Detroit (DTW) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/dtw/anp/detroit-to-annapolis) - [Flights from Frankfurt (FRA) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/fra/anp/frankfurt-to-annapolis) - [Flights from New York (JFK) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/jfk/anp/new-york-to-annapolis) - [Flights from Edmonton (YEG) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yeg/anp/edmonton-to-annapolis) - [Flights from Montreal (YUL) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yul/anp/montreal-to-annapolis) - [Flights from Calgary (YYC) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yyc/anp/calgary-to-annapolis) - [Flights from Toronto (YYZ) to Annapolis (ANP)](https://www.expedia.ca/lp/flights/yyz/anp/toronto-to-annapolis) - [Visit Arundel on the Bay](https://www.expedia.ca/Annapolis-Arundel-On-The-Bay.dx553248635976475949) - [Visit Churchton](https://www.expedia.ca/Churchton.dx6247936) - [Visit Deale](https://www.expedia.ca/Deale.dx55664) - [Maryland Quiet Waters Park](https://www.expedia.ca/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Visit Selby-on-the-Bay](https://www.expedia.ca/Selby-On-The-Bay.dx553248634999271692) - [Shadyside Park](https://www.expedia.ca/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction) - [Car rental Deale](https://www.expedia.ca/Car-Rentals-In-Deale.d55664.Car-Rental-Guide) - [Car rental Highland Beach](https://www.expedia.ca/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide) - [Sixt Ni Rental Cars in Selby-on-the-Bay](https://www.expedia.ca/Sixt-Ni-Car-Rentals-In-Selby-On-The-Bay.d553248634999271692-c1126.Car-Rental-Guide-Suppliers) - [Edgewater Vacation Rentals](https://www.expedia.ca/Edgewater-Vacation-Rentals.d6348965.Travel-Guide-VacationRentals) - [Things to do in Edgewater](https://www.expedia.ca/Things-To-Do-In-Edgewater.d6348965.Travel-Guide-Activities) - [Book Cottages in Shady Side on Expedia.com](https://www.expedia.com/Shady-Side-Cottages.d6264943-aaCottages.Travel-Guide-Accommodation)