Title: Shady Side Apartment Rentals from CA $486 | 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 Apartment Rentals in Shady Side - ![](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 [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=APARTMENT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Shady Side Apartments ![Pool](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/45c5363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/777b4d09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/bce83d29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117370000/117360200/117360157/4f776335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Pool Loft sleeps 4 Cape Saint Claire 10/10 Exceptional (3) "The property is immaculately clean - most important - and very nicely decorated. Everything needed was stocked and available. We did not use the pool as we were out a lot of our stay but it looked lovely. Easy access and handicap accommodating. Would stay again. The only glitch we had was the TV remote but that was more of our problem than the property's. They are all different from state to state and it took us a bit but we got it. Maybe some directions? Host is quickly responsive to... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) maria o. CA $175 CA $501 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/f520f52a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/d5668d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/8e1aa433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68990000/68986300/68986275/0e2deec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Oasis of Annapolis Star Annapolis 10/10 Exceptional (81) "Owners were great hosts. Loved this property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $322 CA $621 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Oasis-Sleep-4-Close-To-Downtown.h68986275.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w904h683x60y0-dec863ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/001f8463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1024h592x0y17-9d1e8161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Cent. Charm in Historic Downtown Annapolis Historic District 9.0/10 Wonderful (13) "This was the perfect location for our visit to the Annapolis Boat Show. We were able to walk everywhere we needed to go. Jennifer has all the amenities from linens to coffee. I would recommend this for anyone visiting the city docks of Annapolis " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandy CA $240 CA $486 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Charming-18th-Cent-Home-In-Historic-Downtown-Annapolis.h92564827.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/27a8090f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/dc6a2b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/w1200h799x0y1-55bb08bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630212/697fbff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Gem: Stylish and Cozy Annapolis 10/10 Exceptional (2) "Clean and nicely decorated. Did not realize it was a basement unit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy B. CA $347 CA $680 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Gem-Stylish-And-Cozy.h117630212.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/14451366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/w1199h800x1y0-94cb1016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/f407739a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117640000/117630300/117630208/99788b82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dean Street's Lower Deck House! Historic District 10/10 Exceptional (2) "This house was the perfect spot for our weekend getaway for my husband, dog and I! It was in a great location and communication re check in and out process was seamless. We plan to come back to Annapolis again and will make sure this is the first thing we book!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin L. CA $296 CA $636 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Annapolis-Hotels-Dean-Streets-Lower-Deck-House.h117630208.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/w1201h914x0y1-e8fa6c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/658833c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/dee76b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/88000000/87580000/87576400/87576375/4478d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids Admiral Heights 10/10 Exceptional (45) "I loved the hosts. Very personable, accomodating with great communication. I plan to work with them again next time we come to Annapolis. Especially for Navy home football games. Perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $536 CA $699 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Gorgeous-Carriage-House-Close-To-USNA.h87576375.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=2025-11-17&endDate=2025-11-18®ionId=6264943&adults=2&lodging=APARTMENT&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-Apartments.d6264943-aaApartments.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Apartments.d6264943-aaApartments.Travel-Guide-Accommodation) ## Top Shady Side Hotel Reviews ![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 "The hotel was very clean. I appreciate the server at breakfast helping us with the waffle maker. The gentleman at the front desk was polite and assisted with any concerns I had. My child attended a BSU and it was a great hotel for an overnight stay." [](https://expedia.ca/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Friendly and welcoming valet and front desk. Beautiful and clean rooms. Disappointed no restaurant but understand. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent " Nice staff. Clean room. all good" [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Hampton Inn & Suites Glenarden/Washington DC](//images.trvl-media.com/lodging/20000000/19350000/19345400/19345309/114260b9_y.jpg) ### Hampton Inn & Suites Glenarden/Washington DC 10/10 Excellent "Nice" [](https://expedia.ca/College-Park-Hotels-Hampton-Inn-Suites-Glenarden.h19345309.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 "Awesome " [](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Lovely room" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it." [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 "Great customer service and housekeeping staff " [](https://expedia.ca/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "I am a healthcare traveler and I work night shift. Unlike most people who go to a hotel, i need a bed for day time sleep and an esrly check in. The front desk agents accommodated my early check in and gave me a clean room at 9am. I went to sleep right away. No noise, no dirty bathroom. Plus the buffet was a huge plus. I booked all my other stays here. This will be home for the next couple of weeks. Everyone had a welcoming smile. " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ## Find out more about Shady Side ## Shady Side Apartments information | Number of reviews | 141 | | --- | --- | | Accommodation | 84 Apartments | | Lowest Price | CA $486 | | Highest Price | CA $699 | ## Frequently asked questions ### What's it like to stay at an apartment in Shady Side? > There are 12 lodging options in Shady Side. Though there aren't many apartments, we can help you search for accommodations that are similar. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can also search for similar property types like vacation homes, condos, or cabins. ### Are you thinking about an apartment for your stay? > An apartment is often more spacious than a traditional hotel room and includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel. ### What's the top apartment for my stay in Shady Side? > Here are some of the favorite apartments in the area: [Luxury Pool Loft sleeps 4](https://www.expedia.ca/Annapolis-Hotels-New-The-Pool-Loft-At-Poplar-Hill.h117360157.Hotel-Information): Located 13.9 mi/22.4 km away in Annapolis. Amenities include fireplaces. Access to onsite laundry facilities is available on site. [Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids](https://www.expedia.ca/Annapolis-Hotels-Gorgeous-Carriage-House-Close-To-USNA.h87576375.Hotel-Information): Located in Annapolis, 9.6 mi/15.4 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. [Downtown St. Michaels | Porch + Pet-Friendly](https://www.expedia.ca/St-Michaels-Hotels-Downtown-St-Michaels-Porch-Pet-Friendly.h119908464.Hotel-Information): 15.9 mi/25.6 km away in St. Michaels. Amenities include private balconies. [Modern Flat in the Heart of St. Michaels – Walk Everywhere](https://www.expedia.ca/St-Michaels-Hotels-The-Heart-Of-St-Michaels-Awaits.h82943888.Hotel-Information): Located in St. Michaels, 16 mi/25.7 km from Shady Side. Includes private balconies and fireplaces. Access to onsite laundry facilities is available on site. ### What will the weather be like when I travel to Shady Side? > Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Shady Side. 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 should I see and do in Shady Side? > Shadyside Park and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Captain Avery Museum is one of the cultural attractions. Other places in town to visit include Franklin Point State Park and Northern Chesapeake Bay. ### What's the best way to get to and around Shady Side? > Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Fort Meade, MD (FME-Tipton), which is located 21.6 mi (34.8 km) from the city center. You can also search for flights into College Park, MD (CGS), which is 24.1 mi (38.7 km) away. 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