Find hotels in Shady Side, MD from $89

These Shady Side insights are based on real traveler data from Expedia, aggregated using AI to help you plan your trip. Updated: August 14, 2026.

Top reasons to visit Shady Side

• Outdoor Recreation: Shady Side offers beautiful parks and scenic areas, perfect for family-friendly outdoor activities.
• Charming Marina: Enjoy the picturesque views and relaxing atmosphere by the Chesapeake Bay at the local marina.
• Historic Exploration: Discover local history through charming historic houses and cultural experiences.
• Vibrant Nightlife: Experience the lively local nightlife with various dining and entertainment options.
• Diverse Accommodations: Choose from cozy bed & breakfasts to convenient hotels, catering to all travelers.

Find great hotels near Shady Side

Discover a range of welcoming accommodations in Shady Side, Maryland, perfect for every kind of traveler. From cozy bed & breakfasts to convenient hotels, you'll find options that cater to business needs and offer pet-friendly and LGBTQIA-inclusive environments. Whether you're seeking hotels near Shady Side or accommodations in the heart of the area, enjoy a memorable stay while exploring this charming destination.

• Comfort Inn Conference Center: Located 13 miles from Shady Side, this budget-friendly hotel boasts an impressive guest rating of 9.2 out of 10. Ideal for families and business travelers alike, the Comfort Inn Conference Center offers a welcoming environment for both leisure and work. Families will appreciate amenities like child-friendly features and a pool gate for safety. Additionally, the hotel is pet-friendly, allowing for a stress-free stay with your furry companions, complete with a service animal policy and specific pet weight allowances.
• Country Inn & Suites by Radisson, Annapolis, MD: Situated 10 miles from Shady Side, this 3-star hotel has earned a guest rating of 9.0 out of 10. The Country Inn & Suites provides a cozy atmosphere for business travelers and pet owners, making it a versatile choice for various visitors. With amenities like a dog exercise area and pet policies in place, you can relax knowing your pets are welcome. The hotel's charming decor and friendly service ensure a comfortable stay, whether for work or leisure.
• Sonesta ES Suites Annapolis: Just 9 miles away from Shady Side, Sonesta ES Suites Annapolis is a 3-star property with a guest rating of 8.8 out of 10. This hotel caters to both business travelers and pet-friendly vacationers, featuring spacious accommodations that feel like home. Guests can take advantage of the hotel's pet policies, which allow dogs with some restrictions, making it a great choice for pet owners. The inviting atmosphere, combined with convenient amenities, makes it a top pick for a comfortable stay.

Where to stay near Shady Side

Shady Side, Maryland, offers a delightful blend of outdoor adventures and scenic beauty, perfect for family vacations. Explore the vibrant nightlife, relax by the stunning Chesapeake Bay, and discover hidden gems like Tacaro Estate. Whether you're enjoying the friendly atmosphere or soaking in the picturesque views, Shady Side promises an unforgettable experience for travelers seeking both relaxation and community charm.

• Annapolis: Nestled about 10 miles from Shady Side, Annapolis is a vibrant city known for its rich history and scenic waterfront. Visitors flock here year-round, especially during the peak months of July to August and October. Families and outdoor enthusiasts will find plenty to enjoy, from exploring the captivating Chesapeake Bay to shopping at local centers. Notable attractions include the United States Naval Academy and beautiful beaches, making it a perfect blend of education, entertainment, and relaxation.
• Upper Marlboro: Located approximately 13 miles from Shady Side, Upper Marlboro offers a family-friendly atmosphere with a touch of urban charm. The city sees a steady influx of visitors, notably during March to April and July. Enjoy outdoor experiences at local parks or catch an exciting game at nearby sports facilities. With shopping centers and educational opportunities, Upper Marlboro is an ideal destination for those looking to immerse themselves in a city-themed experience while enjoying the outdoors.
• Galesville: Just 2 miles from Shady Side, Galesville is a quaint town that beautifully combines outdoor adventure with family-friendly activities. The town experiences a moderate seasonal influx of visitors, peaking from June to August. With its stunning bay views and local parks, Galesville is perfect for those seeking scenic beauty and recreational activities. Families can enjoy the beach and nearby shopping centers, making it a delightful stop for relaxation and exploration.

Things to do near Shady Side

Shady Side, Maryland, is perfect for outdoor family vacations, offering scenic beauty and recreational activities. Visitors can enjoy Shady Side Park and various recreational areas, making it an ideal spot for relaxation and fun. Additionally, there are shopping centers nearby to explore, adding to the charm of this quaint community.

Shopping

In Shady Side, you can explore local shops offering unique gifts and souvenirs. If you're up for a drive, check out the Westfield Annapolis Mall, about 12 miles away, where you'll find a variety of retail stores, dining options, and entertainment for a full day of shopping.

Recreation

Old South Country Club, located 8 miles from Shady Side, offers a luxurious atmosphere perfect for relaxation. Enjoy upscale amenities, including a golf course, spa services, and fine dining, all designed to enhance your wellness experience while soaking in the picturesque surroundings of the countryside.

Adventure

Shady Side, Maryland, offers thrilling kayaking adventures on the scenic Chesapeake Bay, where you can paddle through tranquil waters and enjoy stunning sunsets. Explore nearby parks for hiking and birdwatching, or try fishing off the local piers, immersing yourself in the area's natural beauty.

Nightlife

In Shady Side, the nightlife is relaxed yet vibrant. Visit the local waterfront bars for live music and stunning views. The nearby Annapolis area offers lively pubs and cozy lounges, perfect for unwinding with friends after a day of exploration.

Booking tips and Expedia advantages for Shady Side

• 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, desired location, and preferred hotel type. To find the best prices and deals, 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 through an Expedia package deal.

Find the best attractions in and around Shady Side

Shady Side, Maryland, is perfect for outdoor and family vacations, offering a blend of scenic beauty and cultural experiences. Visitors can explore historic houses, relax in urban parks, and enjoy the marina. With a variety of attractions catering to outdoor enthusiasts and families alike, Shady Side promises a memorable getaway for travelers looking to immerse themselves in nature and local history.

• Shadyside Park: Experience the charm of Shadyside Park, an inviting urban park perfect for family outings and outdoor activities. Enjoy picnics, leisurely walks, and the vibrant community atmosphere.
• Maryland State House: Immerse yourself in history at the Maryland State House, a stunning civic building that showcases rich culture and heritage. Take a guided tour to explore its impressive architecture and learn about Maryland's governmental history.
• Chesapeake Bay Bridge: Marvel at the engineering feat of the Chesapeake Bay Bridge, a modern landmark that connects communities. Enjoy breathtaking views of the bay and surrounding areas as you traverse this iconic structure.

Best time to go to Shady Side

The best time to visit Shady Side is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

When planning your trip to Shady Side, Maryland, you have several airport options. Washington, DC (DCA-Ronald Reagan Washington National) is approximately 28 miles away, with nearby hotels like the 5-star InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 2 miles from the airport. Washington, DC (IAD-Washington Dulles Intl.) is about 51 miles away, offering hotels such as The Westin Washington Dulles Airport, just 1 mile from the terminal. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is the closest at 25 miles, featuring luxurious options like Pendry Baltimore and Four Seasons Hotel, both around 8 miles from the airport with various transportation services available.