Find hotels in Shady Side, MD from $78

Top reasons to visit Shady Side

• Outdoor Activities: Shady Side offers a variety of outdoor adventures, perfect for families and nature enthusiasts, including marinas and parks.
• Charming Community Atmosphere: Experience the friendly vibe of this scenic coastal town, ideal for relaxation and exploration.
• Proximity to Annapolis: Just a short drive away, visitors can enjoy the vibrant culture and attractions of downtown Annapolis.
• Cozy Accommodations: Choose from a range of charming hotels and bed & breakfasts, accommodating diverse traveler needs.
• Rich History: Explore historic houses and cultural sites that showcase the area's unique heritage.

Find great hotels near Shady Side

Welcome to Shady Side, Maryland, where you can find a range of charming accommodations, including hotels and cozy bed & breakfasts. Whether you're seeking a pet-friendly stay or a welcoming environment for LGBTQIA travelers, Shady Side offers various options to suit your needs. Explore the best hotels in the area, perfect for both leisure and business travelers, and enjoy a memorable vacation experience in this picturesque coastal community.

• Comfort Inn Conference Center: Ideal for business travelers, the Comfort Inn Conference Center combines practicality with comfort. Located 13 miles from Shady Side, this hotel is pet-friendly and offers a range of business amenities, including multiple meeting rooms and a fully equipped conference center. The property is designed with convenience in mind, featuring accessible business centers and a prime location in a bustling business district. Its welcoming atmosphere is perfect for both work and leisure, making it a solid choice for professionals on the go.
• Country Inn & Suites by Radisson, Annapolis, MD: Just 10 miles from Shady Side, Country Inn & Suites is a 3-star gem that emphasizes inclusivity and comfort. This hotel is not only pet-friendly, but also proudly supports LGBTQIA travelers, making it a welcoming space for everyone. With 24-hour business center access, multiple meeting rooms, and a spacious conference area, it caters to the needs of corporate guests while providing a cozy atmosphere. Guests appreciate the dog exercise area and thoughtful pet policies, ensuring a pleasant stay for furry companions as well.
• Graduate by Hilton Annapolis: Located 9 miles from Shady Side, the Graduate by Hilton Annapolis offers a sophisticated blend of family-friendly and business-oriented features. This 4-star hotel is perfect for travelers with pets, providing amenities such as food and water bowls and variable pet fees. Business travelers will find essential services like meeting rooms and conference spaces, while families with children can enjoy complimentary cribs. The Graduate stands out for its stylish design and commitment to delivering a memorable stay for all guests.

Where to stay near Shady Side

Shady Side, Maryland, offers a delightful mix of outdoor adventures and family-friendly experiences. Just a short drive from vibrant downtown Annapolis, visitors can enjoy the peaceful atmosphere while exploring the scenic Chesapeake Bay. This charming location is perfect for a relaxing getaway, where you can immerse yourself in the friendly community and discover the beauty of the region. Whether you're seeking a quiet escape or a taste of city life, Shady Side has something for everyone.

• Annapolis: Located 10 miles from Shady Side, Annapolis is a vibrant city known for its rich history and charming waterfront. As the state capital of Maryland, it offers a mix of educational experiences, shopping opportunities, and outdoor activities. Visitors flock to Annapolis for family-friendly attractions and city-themed explorations, especially during the peak months from May to July. Highlights include historic sites like the U.S. Naval Academy, beautiful beaches, and scenic lakes. Enjoy shopping at local centers and indulging in the area’s diverse culinary scene while taking in the picturesque views of the Chesapeake Bay.
• Deale: Just 5 miles away from Shady Side, Deale is a small yet inviting city perfect for outdoor enthusiasts and adventure seekers. Known for its stunning scenery, visitors are drawn to Deale primarily in June to July and October. The town boasts recreational areas, shopping centers, and a laid-back atmosphere. Nature lovers can explore nearby beaches, lakes, and the national state park, which offers ample opportunities for hiking, fishing, and relaxing in nature. Whether you’re looking for a peaceful getaway or thrilling outdoor activities, Deale has something for everyone.
• Galesville: A mere 2 miles from Shady Side, Galesville is a quaint city that perfectly balances outdoor family fun and scenic beauty. With a peak in visitor numbers from June to August, this charming area offers recreational activities, educational experiences, and local shopping options. Galesville is well-known for its beautiful beaches, serene lakes, and inviting urban parks, making it an ideal spot for picnics, leisurely walks, or simply soaking up the sun. This close-knit community is sure to provide a relaxing and enjoyable atmosphere for all travelers.

Things to do near Shady Side

Shady Side, Maryland, is perfect for outdoor family vacations and urban adventures. Visitors can enjoy activities in recreational areas, explore educational sites, and indulge in shopping at local mall centers. With its charming community atmosphere, Shady Side offers a delightful blend of relaxation and engagement for tourists looking to experience the best of this scenic coastal town.

Shopping

In Shady Side, visit the Wild Bird Center, an 8-mile drive offering unique gifts for nature enthusiasts. If you're up for a drive, check out Annapolis Mall and Westfield Annapolis Mall, both located 10 miles away, featuring a mix of entertainment, shopping, and dining options.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere perfect for sports enthusiasts. South River Golf Links invites you to enjoy a round of golf amidst picturesque outdoor settings. For a touch of luxury, visit Old South Country Club, where you can unwind in a refined environment and enjoy premium amenities.

Adventure

At Chesapeake Beach Water Park, located 10 miles from Shady Side, enjoy thrilling water slides and family-friendly attractions for a day of fun. Experience the excitement of sailing at Annapolis Sailing School, 9 miles away, offering outdoor adventure on the beautiful waters. Hike the scenic B&A Trail, situated 18 miles from Shady Side, for breathtaking views and natural beauty.

Nightlife

Experience a vibrant nightlife in Shady Side with a visit to The Colonial Players for a theatrical evening filled with culture and romance. For a more adventurous vibe, check out Annapolis Bowl or Crofton Bowl, both offering exciting arcade games and fun-filled activities just a short drive away.

Booking tips and Expedia advantages for Shady Side

To save money on your trip to Shady Side, Maryland, consider visiting during the off-peak months of December to February for lower rates. Booking your stay on a Monday can also help reduce costs, while Saturdays tend to be pricier. Use Expedia to find budget-friendly accommodations by sorting options from lowest to highest price, and explore package deals that combine flights and hotels for additional savings. Joining the Expedia One Key membership can unlock exclusive discounts and allow you to earn OneKeyCash for future stays. Don't forget to look for free local activities to enhance your experience without extra 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: Utilize Expedia's search tool to refine your options based on your budget, preferred location, and the type of hotel you desire. To find the best prices and deals, simply arrange the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Shady Side with your flights and activities by opting for an Expedia package deal.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions in and around Shady Side

Shady Side, Maryland, offers a perfect blend of outdoor activities, family fun, and urban exploration. Visitors can enjoy local attractions such as marinas, historic houses, and urban parks that cater to those seeking cultural experiences and nature. Whether you're looking to relax by the water or explore the rich history of the area, Shady Side has something for everyone to enjoy.

• U.S. Naval Academy: Located 10 miles from Shady Side, this prestigious military academy offers a blend of history and stunning architecture. Visitors can explore the beautiful campus, learn about naval traditions, and enjoy scenic views along the waterfront.
• Shadyside Park: Situated within Shady Side, this urban park is a perfect spot for families to unwind. With playgrounds, picnic areas, and walking trails, it provides a relaxing outdoor atmosphere in a vibrant city setting.
• Captain Avery Museum: Also located in Shady Side, this historic house museum showcases local maritime history and culture. Visitors can engage with exhibits and artifacts that highlight the area's rich heritage and connection to the Chesapeake Bay.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.8°F (2.1°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	38.1°F (3.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	45.0°F (7.2°C)	Light Rain	Mostly Sunny	Average	Average
April	55.0°F (12.8°C)	Light Rain	Mostly Sunny	Average	Average
May	64.2°F (17.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
June	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	78.3°F (25.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	76.6°F (24.8°C)	Light Rain	Mostly Sunny	Average	Average
September	70.7°F (21.5°C)	Light Rain	Mostly Sunny	Average	Average
October	60.4°F (15.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	41.5°F (5.3°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Shady Side

Visiting Shady Side, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is situated 28 miles away, with hotels like the InterContinental Washington D.C. - The Wharf and Riggs Washington DC just 2 to 3 miles from the airport. Another option is Washington, DC (IAD-Washington Dulles Intl.), located 51 miles away, featuring the Hyatt Regency Dulles and Hilton Washington Dulles Airport within a couple of miles. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), only 25 miles from Shady Side, offers luxury accommodations like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both about 8 miles away, providing shuttle services to the airport.