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

Shady Side Hotels

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Oct 6 - Oct 7
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Oct 7 - Oct 8
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Oct 9 - Oct 11
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Oct 16 - Oct 18

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Our top choices for Shady Side hotels

1. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Beverly
P11,877
P13,540 total
includes taxes & fees
Oct 29 - Oct 30
Anchored Inn at Hidden Harbour Marina

2. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Michele
P6,060
P6,909 total
includes taxes & fees
Oct 12 - Oct 13
DoubleTree by Hilton Hotel Annapolis

3. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Lisa
P7,444
P8,486 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis

4. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Cynthia
P6,890
P7,855 total
includes taxes & fees
Oct 11 - Oct 12
Crowne Plaza Annapolis by IHG

5. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
Canada
Omer
P6,881
P7,844 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express & Suites Annapolis by IHG

6. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Francine
P9,044
P10,039 total
includes taxes & fees
Oct 21 - Oct 22
Rod 'N' Reel Resort

7. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Ashley
P5,343
P8,230 total
includes taxes & fees
Nov 1 - Nov 2
Historic Inns of Annapolis

8. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Mark
P9,194
P10,482 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis

9. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
P12,448
P14,191 total
includes taxes & fees
Oct 25 - Oct 26
The Westin Annapolis

10. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Titus
P6,818
P7,705 total
includes taxes & fees
Oct 7 - Oct 8
Comfort Inn Conference Center

11. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Philip
P5,700
P6,498 total
includes taxes & fees
Oct 28 - Oct 29
Sonesta ES Suites Annapolis

12. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United Kingdom
petra
P7,140
P8,139 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Annapolis Downtown

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

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
P5,955
P6,789 total
includes taxes & fees
Oct 26 - Oct 27
Country Inn & Suites by Radisson, Annapolis, MD

14. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Courtney
P6,327
P7,213 total
includes taxes & fees
Oct 28 - Oct 29
Hampton Inn & Suites Annapolis

15. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
Silvia
P5,011
P5,713 total
includes taxes & fees
Oct 12 - Oct 13
Best Western Annapolis

16. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Jim
P6,550
P7,468 total
includes taxes & fees
Oct 25 - Oct 26
Courtyard by Marriott Annapolis

17. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
P15,898
P18,123 total
includes taxes & fees
Oct 12 - Oct 13
Annapolis Waterfront Hotel, Autograph Collection

18. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
P6,327
P7,213 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Annapolis

19. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
P9,508
P10,554 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina

20. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
United States
Halima
P8,388
P9,479 total
includes taxes & fees
Oct 19 - Oct 20
Courtyard by Marriott Bowie
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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 Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Very close to getting public transport."
Alicia 1-night trip
Posted 5 hours ago
Comfort Inn Largo-Washington DC East
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"my cozy room pet friendly staff"
victoria 3-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Largo/Washington DC
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent
"This hotel was clean, well maintained, and conveniently located. The staff was helpful and pleasant. I would recommend a stay at the Microtel in Gambrills to anyone looking for a convenient stay in the area!"
Beverley 2-night trip
Posted 10 hours ago
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."
Lauren 2-night trip
Posted 12 hours ago
Hilton Garden Inn Annapolis Downtown
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
Silvia 1-night trip
Posted 1 day ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The gym was really small. The rooms are very nice"
Henrik 2-night trip
Posted 2 days ago
Rod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"It’s was a great experience besides the two roaches I found in the bathroom"
Natasha R 3-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 5 days ago
St Michaels Inn

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
P5,011
P5,713 total
Oct 12 - Oct 13
includes taxes & fees
7.8/10 Good! (1,005 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
P5,573
P6,131 total
Oct 13 - Oct 14
includes taxes & fees
St Michaels Inn
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD
P5,849
P6,667 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,160 reviews)
Microtel Inn & Suites by Wyndham Gambrills/Odenton
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
P6,751
P7,494 total
Oct 12 - Oct 13
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Best Western Kent Narrows Inn
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
P6,818
P7,705 total
Oct 7 - Oct 8
includes taxes & fees
Comfort Inn Conference Center
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
P6,881
P7,844 total
Oct 25 - Oct 26
includes taxes & fees
Holiday Inn Express & Suites Annapolis by IHG

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. Features free self parking, an indoor pool, and complimentary wireless internet access. Rod 'N' Reel Resort and Comfort Inn Largo-Washington DC East 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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