A river with boats, a marina, and a town with houses and buildings.

Shady Side Hotels

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Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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Our top choices for Shady Side hotels

Reserve now, pay later
Breakfast included
Bed & breakfast
Hotel
Family friendly

1. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
P7,954
P9,067 total
includes taxes & fees
Aug 23 - Aug 24
SpringHill Suites by Marriott Annapolis

2. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Rachel
P7,337
P8,291 total
includes taxes & fees
Aug 23 - Aug 24
Comfort Inn Conference Center

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
eliana
P6,032
P6,877 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis

4. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
P5,870
P6,692 total
includes taxes & fees
Sep 13 - Sep 14
Country Inn & Suites by Radisson, Annapolis, MD

5. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
Gambrills
United States
James
P5,675
P6,470 total
includes taxes & fees
Aug 30 - Aug 31
Microtel Inn & Suites by Wyndham Gambrills

6. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Dale
P12,425
P14,165 total
includes taxes & fees
Sep 15 - Sep 16
Anchored Inn at Hidden Harbour Marina

7. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
P5,673
P6,467 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Annapolis

8. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
United States
Frank
P6,227
P7,099 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express & Suites Annapolis by IHG

9. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
United States
Yolanda
P8,268
P9,343 total
includes taxes & fees
Aug 31 - Sep 1
Courtyard by Marriott Bowie

10. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
P4,939
P5,631 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Annapolis

11. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
P5,670
P8,577 total
includes taxes & fees
Aug 27 - Aug 28
Historic Inns of Annapolis

12. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
John
P5,981
P6,818 total
includes taxes & fees
Aug 30 - Aug 31
Sonesta ES Suites Annapolis

13. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Heather
P6,782
P7,732 total
includes taxes & fees
Sep 1 - Sep 2
Crowne Plaza Annapolis by IHG

14. Executive Inn And Suites

Executive Inn And Suites
Upper Marlboro
United States
Will
P5,244
P5,926 total
includes taxes & fees
Aug 23 - Aug 24
Executive Inn And Suites

15. Staybridge Suites Washington DC East - Largo by IHG

Staybridge Suites Washington DC East - Largo by IHG
Upper Marlboro
United States
Amy
P7,831
P8,849 total
includes taxes & fees
Sep 8 - Sep 9
Staybridge Suites Washington DC East - Largo by IHG

16. Hampton Inn Bowie

Hampton Inn Bowie
Bowie
United States
james
P6,017
P6,799 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn Bowie

17. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Charles Eric
P10,420
P11,879 total
includes taxes & fees
Aug 30 - Aug 31
The Westin Annapolis

18. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
P6,017
P6,859 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Annapolis

19. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
P24,455
P27,879 total
includes taxes & fees
Sep 7 - Sep 8
The Inn at Tacaro Estate

20. Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC
Lanham
United States
Jeffrey
P6,522
P7,370 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Glenarden/Washington DC
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Stay near popular Shady Side attractions

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.
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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.
See properties

Learn more about Shady Side

Love dining out, parks, and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"The hotel is very clean and well maintained. There are nearby stores you could walk to if you wanted to do last minute shopping. The staff are polite."
Kesiena 3-night trip
Posted 3 hours ago
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."
Erich 1-night trip
Posted 16 hours ago
Annapolis Waterfront Hotel, Autograph Collection
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good
"Reasonable value for the money"
Frank 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Annapolis by IHG
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."
Michael 3-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Great stay"
Pili 2-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast bacon was inedible, but breakfast otherwise substantial."
Maureen 1-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD
P4,871
P5,504 total
Aug 23 - Aug 24
includes taxes & fees
WoodSpring Suites Washington DC East Arena Drive
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
P5,508
P6,059 total
Aug 31 - Sep 1
includes taxes & fees
St Michaels Inn
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
P5,675
P6,470 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,131 reviews)
Microtel Inn & Suites by Wyndham Gambrills
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
P6,067
P6,917 total
Sep 16 - Sep 17
includes taxes & fees
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
P6,227
P7,099 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
P7,337
P8,291 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (1,022 reviews)
Comfort Inn Conference Center

Find out more about Shady Side

Top reasons to visit Shady Side

  • Picturesque Scenery: Shady Side offers stunning views and a tranquil atmosphere, perfect for relaxation and outdoor activities.
  • Outdoor Adventures: Ideal for nature enthusiasts, visitors can engage in various recreational pursuits at marinas and parks.
  • Rich Local Culture: Explore historic houses and enjoy the charming local atmosphere that reflects the area's heritage.
  • Family-Friendly Activities: The destination caters to families with diverse attractions, ensuring fun for all ages.
  • Varied Accommodation: A range of lodging options, from cosy bed and breakfasts to modern hotels, accommodates all travellers.

Find great hotels near Shady Side

Discover a delightful range of accommodation options in Shady Side, Maryland, perfect for all types of travellers. Whether you prefer a cosy bed and breakfast or a modern hotel, you'll find choices that cater to business needs, pet-friendly policies, and an LGBTQIA welcoming environment. Explore the best hotels in the area and enjoy a memorable stay in this charming coastal community.

  • Country Inn & Suites by Radisson, Annapolis, MD: Located 16.1km from Shady Side, the Country Inn & Suites by Radisson, Annapolis, MD offers a warm and welcoming environment. This 3-star hotel caters to LGBTQIA guests and is pet-friendly, making it an excellent choice for those travelling with furry companions. The amenities include a dedicated dog exercise area and a pet policy that ensures comfort for all guests. With its emphasis on business travel, this hotel is equipped with essential facilities for professionals on the go, ensuring a productive stay while enjoying a relaxing atmosphere.
  • Comfort Inn Conference Center: Situated 20.9km from Shady Side, the Comfort Inn Conference Center is designed with business travellers in mind. This hotel boasts a convenient location and a range of amenities that cater to both work and leisure. Pets are welcome, allowing guests to bring their beloved animals along for the trip. The hotel’s business facilities ensure that all professional needs are met, making it an ideal spot for those needing to balance work commitments with a comfortable stay.
  • Historic Inns of Annapolis: Just 16.1km from Shady Side, the Historic Inns of Annapolis is a charming 3.5-star property located in the heart of the city. This hotel is perfect for LGBTQIA travellers and offers a unique city-themed experience. Guests will appreciate the rich history and character of the inn, along with modern amenities that enhance their stay. Its central location makes exploring Annapolis effortless, allowing for a delightful mix of business and leisure in a culturally vibrant setting.

Where to stay near Shady Side

Shady Side, Maryland, offers a delightful retreat for those seeking a blend of outdoor charm and family-friendly adventures. Just a short distance from vibrant downtown Annapolis, visitors can indulge in the serene beauty of the Chesapeake getaway. Whether exploring the tranquil surroundings or engaging with the friendly local atmosphere, Shady Side promises a relaxing escape with stunning scenery, making it an ideal base for unforgettable experiences just beyond its quiet locale.

  • Annapolis: Situated approximately 16.1km from Shady Side, Annapolis is a vibrant city known for its rich history and charming waterfront. This city sees a consistent flow of visitors year-round, particularly during the summer months from June to August. Visitors flock to Annapolis for family-oriented activities, business engagements, and city-themed experiences. Notable highlights include its renowned educational institutions, shopping centres, and local landmarks such as the picturesque beach and bustling tourist precinct. The blend of historical charm and modern amenities makes Annapolis a delightful stop on your journey.
  • Galesville: Just 3.2km from Shady Side, Galesville is a quaint city that offers a serene escape into nature. With moderately seasonal travel patterns, peak visitor numbers occur from June to August, with additional waves in the autumn months. Galesville is perfect for those seeking outdoor adventure and romantic scenery, featuring recreational areas and beautiful lakeside spots. The local urban park invites leisurely strolls, while the nearby beach provides a perfect spot for relaxation. Galesville’s enchanting surroundings make it ideal for a peaceful getaway.
  • Churchton: Located about 4.8km away from Shady Side, Churchton is a charming city that attracts visitors seeking outdoor exploration and romantic vistas. Its visitor numbers peak during the months of February and June to July, as well as in October. Churchton boasts splendid recreational areas and a scenic boardwalk that invites leisurely walks. The proximity to beautiful lakes, stunning beaches, and the national state park enhances its appeal. Whether you're looking for adventure or a quiet retreat, Churchton offers a captivating experience.

Things to do near Shady Side

Shady Side offers a delightful escape for families and nature enthusiasts, with its picturesque scenery and outdoor activities. Visitors can enjoy various recreational areas, engage in educational pursuits, and explore local shopping centres, making it an ideal destination for a relaxing holiday.

Shopping

If you're up for a drive, the Westfield Annapolis Mall offers a vibrant shopping experience with entertainment options, located 16.1km away. Closer to Shady Side, the Wild Bird Center, 12.9km away, is perfect for unique gifts, while Marlborough Village Center, 22.5km away, boasts a lovely family-oriented atmosphere.

Recreation

Navy-Marine Corps Memorial Stadium, located 16.1km from Shady Side, offers an energetic atmosphere for sports enthusiasts. For outdoor relaxation, South River Golf Links, 9.7km away, provides scenic golfing amidst nature. Experience luxury at Old South Country Club, situated 12.9km from Shady Side, perfect for unwinding.

Adventure

Chesapeake Beach Water Park offers exhilarating water slides and family-friendly attractions, perfect for a thrilling day out. For nature enthusiasts, the St Michaels Nature Trail provides a scenic outdoor adventure. If you're seeking excitement on the water, Annapolis Sailing School is ideal for honing your sailing skills.

Nightlife

In Shady Side, The Colonial Players theatre offers a charming blend of romance and culture, perfect for an intimate evening. For a lively family outing, the Annapolis Bowl arcade provides thrilling adventures, while Regal Waugh Chapel cinema presents a mix of entertainment and romance for a perfect night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shady Side

To save money on your trip to Shady Side, consider visiting during the off-peak months of December to February when accommodation prices are significantly lower, especially on Mondays. Avoid Saturdays for the highest rates. Use Expedia to refine your search for budget-friendly hotels and explore package deals that combine flights and activities for greater savings. Additionally, take advantage of free local activities and consider walking or using public transport to minimise travel costs.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Shady Side are December to February, where the prices are slightly lower. This is in comparison to May to July, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shady Side is Monday. The most expensive day to stay in Shady Side is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, including your budget, preferred location, and the type of hotel you desire. To discover the most affordable prices and offers, organise the price filter from lowest to highest.
  • Consider bundling your trip: You can enjoy considerable savings by combining your Shady Side hotel reservations with your flights and activities through an Expedia package.

Find the best attractions near Shady Side

Shady Side is an ideal destination for outdoor enthusiasts and families seeking scenic vacations. Visitors can explore a variety of attractions, including marinas, historic houses, and urban parks, all of which offer a mix of culture and outdoor experiences. Whether you're looking to relax by the water or delve into the area's history, Shady Side caters to diverse interests, ensuring a memorable trip for all.

  • Chesapeake Bay Bridge: This modern marvel spans the bay, offering stunning views and an exhilarating drive. With its impressive architecture, the bridge connects you to the vibrant cities and coastal towns, making it a must-see landmark.
  • Sandy Point State Park: A haven for outdoor enthusiasts, this national park boasts picturesque scenery and diverse recreational activities. From sunbathing on the sandy shores to hiking trails, it's an ideal spot for adventure seekers and nature lovers alike.
  • Maryland State House: Steeped in history, this historic civic government building is the oldest state capitol still in continuous legislative use. Explore its rich culture and fascinating architecture, making it a key highlight of your trip.

Best time to go to Shady Side

The best time to visit Shady Side can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Shady Side falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Shady Side falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.8°F (2.1°C)Light RainMostly SunnyAverageSlightly Low
February38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnySlightly HighSlightly High
June73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnySlightly HighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyAverageAverage
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnySlightly LowAverage
November48.7°F (9.3°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Shady Side

When visiting Shady Side, Maryland, you have convenient access to three major airports. Ronald Reagan Washington National Airport (DCA) is situated 45.1km away, with excellent hotels nearby such as the 5-star Salamander Washington DC and Riggs Washington DC, both approximately 2 to 4.8km from the airport. Washington Dulles International Airport (IAD), located 82.1km away, offers nearby accommodations like the Hyatt Regency Dulles, just 1.6km from the airport. Baltimore Washington International Airport (BWI) is the closest at 40.2km, with luxurious options like the Sagamore Pendry Baltimore, 12.9km away, providing various transportation services for easy airport access.

Frequently asked questions

Where is the best place for a stay in Shady Side?
DoubleTree by Hilton Hotel Annapolis, located 9.8 mi (15.8 km) from the heart of Shady Side, is a top choice for your stay based on our traveler data. Two other choices for your trip to the area are Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Shady Side.
If I need to cancel my hotel reservation in Shady Side, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
What are some accommodations with pools in Shady Side?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Rod 'N' Reel Resort and St Michaels Inn are two additional hotels that offer an onsite pool. View all hotels with pools in Shady Side.
What is staying in Shady Side like?
Visitors can enjoy all that Shady Side has to offer including the shopping, restaurants, and parks. Tourists can also enjoy so much more including its museums. In Shady Side, there are 15 hotels and other accommodations to choose from. Find out more about Shady Side.
What should I see while I'm in Shady Side?
Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay, and Shadyside Park. A couple of additional sights to add to your agenda are Captain Avery Museum and Franklin Point State Park. Check out what more to see and do in Expedia's Shady Side guide.
What's the weather like 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.

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