Title: Visit Shady Side: 2026 Travel Guide for Shady Side, Maryland | Expedia.com

[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)

# Shady Side, MD

## Travel Guide

## Visit Shady Side

Things to do

- Shady Side Hotel Deals
- Vacation Rentals in Shady Side

![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

$98 nightly

$110 total

Feb 19 - Feb 20

Total with taxes and fees

Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Northwest ...

8.2/10 Very Good! (1,007 reviews)

Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important.

Reviewed on Feb 1, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F19%2F2026&endDate=2%2F20%2F2026&selected=21463&PinnedHotelID=21463&HadPinnedHotel=true&regionId=6264943)

![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Historic Inns of Annapolis

58 State Circle Annapolis MD

$229 nightly

$261 total

Feb 26 - Feb 27

Total with taxes and fees

Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...

9/10 Wonderful! (1,884 reviews)

Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!

Reviewed on Jan 31, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F26%2F2026&endDate=2%2F27%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true&regionId=6264943)

![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Graduate by Hilton Annapolis

126 West St Annapolis MD

$156 nightly

$178 total

Feb 22 - Feb 23

Total with taxes and fees

Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...

9.2/10 Wonderful! (1,001 reviews)

Everything! The hotel was clean, great location, and the front desk clerk was kind and helpful!

Reviewed on Jan 29, 2026

[](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true&regionId=6264943)

[See all 1,183 properties in Shady Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026&regionId=6264943)

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.

![The Blue Crab Beach House - Free beach passes ](https://images.trvl-media.com/lodging/79000000/78610000/78601600/78601522/6054db72_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Blue Crab Beach House - Free beach passes 

 North Beach MD

Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...

10/10 Exceptional! (78 reviews)

Everything was fine and comfortable

Reviewed on Dec 27, 2025

[](https://expedia.com/North-Beach-Hotels-The-Blue-Crab-Beach-House.h78601522.Hotel-Information)

![Floating 2 bed 2 bath condo stunning views of the bay ](https://images.trvl-media.com/lodging/106000000/105760000/105758700/105758639/9f651e90_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Floating 2 bed 2 bath condo stunning views of the bay 

 Stevensville MD

Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...

6.2/10 (7 reviews)

Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ...

Reviewed on Oct 8, 2025

[](https://expedia.com/Stevensville-Hotels-Floating-2-Bed-2-Bath-Condo-Stunning-Views-Of-The-Bay.h105758639.Hotel-Information)

![Mid-Century Modern on Private Beach, Designed by Award Winning Architect!](https://images.trvl-media.com/lodging/67000000/66770000/66764300/66764223/6b89611c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

 Chesapeake Beach MD

Book a stay at this beach vacation home in Chesapeake Beach. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Breezy Point Beach and Bruce ...

10/10 Exceptional! (85 reviews)

What a fantastic spot! The views are amazing. The kitchen was the best-appointed we’ve ever experienced. The heated floors for winter were wonderful.

Reviewed on Dec 1, 2025

[](https://expedia.com/Chesapeake-Beach-Hotels-Architectural-Gem.h66764223.Hotel-Information)

[See all properties in Shady Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6264943&sort=VACATION_RENTAL)

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.

## Check Shady Side hotel availability

[Tonight

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2026-02-05&endDate=2026-02-06)[Feb 5 - Feb 6](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2026-02-05&endDate=2026-02-06)

[Tomorrow night

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2026-02-06&endDate=2026-02-07)[Feb 6 - Feb 7](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2026-02-06&endDate=2026-02-07)

[This weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)[Feb 6 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2%2F6%2F2026&endDate=2%2F8%2F2026)

[Next weekend

](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6264943&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)

### Popular places to visit

#### Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants. 

[](https://expedia.com/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction)

#### Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants. 

[](https://expedia.com/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction)

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- [Hotels near Captain Avery Museum ](https://www.expedia.com/Captain-Avery-Museum-Hotels.0-l6263322-0.Travel-Guide-Filter-Hotels)
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- [Motels in Galesville ](https://www.expedia.com/Galesville-Motels.d6264947-aaMotels.Travel-Guide-Accommodation)
- [Churchton Hotels ](https://www.expedia.com/Churchton-Hotels.d6247936.Travel-Guide-Hotels)
- [B&B in Churchton ](https://www.expedia.com/Churchton-Bed-And-Breakfast.d6247936-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Churchton ](https://www.expedia.com/Churchton-Motels.d6247936-aaMotels.Travel-Guide-Accommodation)
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- [3 Star Hotels in Churchton ](https://www.expedia.com/3Star-Churchton-Hotels.s30-0-d6247936.Travel-Guide-Filter-Hotels)
- [Mayo Hotels ](https://www.expedia.com/Mayo-Hotels.d553248634998988486.Travel-Guide-Hotels)
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- [West River Hotels ](https://www.expedia.com/West-River-Hotels.d553248635975860906.Travel-Guide-Hotels)
- [Deale Hotels ](https://www.expedia.com/Deale-Hotels.d55664.Travel-Guide-Hotels)
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- [Edgewater Hotels ](https://www.expedia.com/Edgewater-Hotels.d6348965.Travel-Guide-Hotels)
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- [Extended Stay Hotels in Edgewater ](https://www.expedia.com/Edgewater-Hotels-Extended-Stay-Hotels.0-0-d6348965-tExtendedStayHotels.Travel-Guide-Filter-Hotels)

- [Flights to Churchton ](https://www.expedia.com/Cheap-Flights-To-Churchton.d6247936.Travel-Guide-Flights)
- [Flights to Deale ](https://www.expedia.com/Cheap-Flights-To-Deale.d55664.Travel-Guide-Flights)
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- [Flights to Edgewater ](https://www.expedia.com/Cheap-Flights-To-Edgewater.d6348965.Travel-Guide-Flights)

- [Shadyside Park ](https://www.expedia.com/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction)
- [Captain Avery Museum ](https://www.expedia.com/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction)
- [Visit Galesville ](https://www.expedia.com/Galesville.dx6264947)
- [Visit Churchton ](https://www.expedia.com/Churchton.dx6247936)
- [Smithsonian Environmental Research Center ](https://www.expedia.com/Smithsonian-Environmental-Research-Center-Edgewater.d553248621532662265.Vacation-Attraction)
- [Visit Deale ](https://www.expedia.com/Deale.dx55664)
- [Visit Lothian ](https://www.expedia.com/Lothian.dx3000440697)
- [Visit Tracys Landing ](https://www.expedia.com/Tracys-Landing.dx3000440927)
- [Visit Oyster Harbor ](https://www.expedia.com/Annapolis-Oyster-Harbor.dx553248635976482330)
- [Thanksgiving Farm Wines ](https://www.expedia.com/Thanksgiving-Farm-Wines-Maryland.d553248621532662264.Vacation-Attraction)
- [Visit Edgewater ](https://www.expedia.com/Edgewater.dx6348965)
- [Maryland Quiet Waters Park ](https://www.expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction)

- [Car rentals near Captain Avery Museum ](https://www.expedia.com/Car-Rentals-In-Captain-Avery-Museum.d6263322.Car-Rental-Guide)
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- [Car rentals near Cape Anne ](https://www.expedia.com/Car-Rentals-In-Cape-Anne.d553248635976386052.Car-Rental-Guide)
- [Car rentals near Deale Beach ](https://www.expedia.com/Car-Rentals-In-Deale-Beach.d553248635975876712.Car-Rental-Guide)
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- [Car rentals near Highland Beach ](https://www.expedia.com/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide)
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- [Car rentals near Edgewater ](https://www.expedia.com/Car-Rentals-In-Edgewater.d6348965.Car-Rental-Guide)

- [Churchton Vacation Rentals ](https://www.expedia.com/Churchton-Vacation-Rentals.d6247936.Travel-Guide-VacationRentals)
- [Deale Vacation Rentals ](https://www.expedia.com/Deale-Vacation-Rentals.d55664.Travel-Guide-VacationRentals)
- [Edgewater Vacation Rentals ](https://www.expedia.com/Edgewater-Vacation-Rentals.d6348965.Travel-Guide-VacationRentals)

- [Things to do in Edgewater ](https://www.expedia.com/Things-To-Do-In-Edgewater.d6348965.Travel-Guide-Activities)

- Cities near Shady Side
- Places of interest

[Churchton](https://expedia.com/Churchton.dx6247936)[Galesville](https://expedia.com/Galesville.dx6264947)

- [Shadyside Park ](https://expedia.com/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction)
- [Captain Avery Museum ](https://expedia.com/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction)
- [U.S. Naval Academy ](https://expedia.com/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction)
- [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction)
- [Chesapeake Bay Bridge ](https://expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction)
- [Anne Arundel Medical Center ](https://expedia.com/Anne-Arundel-Medical-Center-Annapolis.d553248621580159030.Vacation-Attraction)
- [Sandy Point State Park ](https://expedia.com/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction)
- [Annapolis City Dock ](https://expedia.com/Annapolis-City-Dock-Historic-District.d553248633992240262.Vacation-Attraction)
- [Show Place Arena ](https://expedia.com/Show-Place-Arena-Upper-Marlboro.d6091739.Vacation-Attraction)
- [Maryland State House ](https://expedia.com/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction)
- [Navy-Marine Corps Memorial Stadium ](https://expedia.com/Navy-Marine-Corps-Memorial-Stadium-Annapolis.d6091645.Vacation-Attraction)
- [Chesapeake Bay Maritime Museum ](https://expedia.com/Chesapeake-Bay-Maritime-Museum-Downtown-St-Michaels.d553248633992441010.Vacation-Attraction)
- [Westfield Annapolis Mall ](https://expedia.com/Westfield-Annapolis-Mall-Annapolis.d6172637.Vacation-Attraction)
- [Annapolis Mall Shopping Center ](https://expedia.com/Annapolis-Mall-Shopping-Center-Annapolis.d553248621563220690.Vacation-Attraction)
- [Breezy Point Beach ](https://expedia.com/Breezy-Point-Beach-Chesapeake-Beach.d553248621532662089.Vacation-Attraction)
- [St. Michaels Winery ](https://expedia.com/St-Michaels-Winery-Downtown-St-Michaels.d553248633992438808.Vacation-Attraction)
- [Annapolis Maritime Museum ](https://expedia.com/Annapolis-Maritime-Museum-Eastport.d553248621532662325.Vacation-Attraction)
- [Annapolis Harbor Center Shopping Center ](https://expedia.com/Annapolis-Harbor-Center-Shopping-Center-Annapolis.d553248621563220686.Vacation-Attraction)
- [Bowie State University ](https://expedia.com/Bowie-State-University-Bowie.d6075472.Vacation-Attraction)
- [Maryland Quiet Waters Park ](https://expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction)
- [Maryland Hall for Creative Arts ](https://expedia.com/Maryland-Hall-For-Creative-Arts-Annapolis.d553248621580159031.Vacation-Attraction)
- [William Paca House ](https://expedia.com/William-Paca-House-Historic-District.d6077398.Vacation-Attraction)
- [Chesapeake Beach Water Park ](https://expedia.com/Chesapeake-Beach-Water-Park-Chesapeake-Beach.d553248621532662257.Vacation-Attraction)
- [Prince George's Community College ](https://expedia.com/Prince-Georges-Community-College-Upper-Marlboro.d6283667.Vacation-Attraction)
- [Northern Chesapeake Bay ](https://expedia.com/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction)
- [Chesapeake Bay Environmental Center ](https://expedia.com/Chesapeake-Bay-Environmental-Center-Grasonville.d553248621561196328.Vacation-Attraction)
- [Renditions Golf Club ](https://expedia.com/Renditions-Golf-Club-Davidsonville.d553248621532662195.Vacation-Attraction)

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