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

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Our top choices for Shady Side hotels

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
An aerial view of a coastal town with a marina, houses, and a bridge in the background.
A spacious indoor area with brick walls, multiple tables and chairs, and string lights.
A marina with multiple boats docked during sunset.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Susan
$148 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Historic Inns of Annapolis
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.
A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

2. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Crystal
$162 nightly
$180 total
Oct 12 - Oct 13
Total with taxes and fees
Rod 'N' Reel Resort
A hotel with a modern design, featuring a prominent 'La Quinta' sign, a covered entrance, and a well-lit facade.
A hotel lobby with a seating area featuring purple chairs, a small table, and a fireplace. There is a reception desk and a wall-mounted TV.
A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.
A hotel room with a dining area featuring a table and chairs, a flat-screen TV mounted on a brick wall, and a small fireplace with a built-in TV.

3. La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
Linthicum Heights
United States
Ashley
$73 nightly
$83 total
Oct 4 - Oct 5
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport
A modern bar area with a central island, multiple shelves of bottles, and a television screen.
A modern hotel lobby with a brick floor, large planters with flowers, and a glass entrance.
A well-lit entrance to a hotel with a modern building, a curved driveway, and surrounding greenery.
A modern hotel lobby with a bar area, seating arrangements, and a large window providing a view of the city.

4. Crowne Plaza College Park - Washington DC by IHG

Crowne Plaza College Park - Washington DC by IHG
Greenbelt
United States
Andrea
$99 nightly
$112 total
Oct 25 - Oct 26
Total with taxes and fees
Crowne Plaza College Park - Washington DC by IHG
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

5. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Joanna
$97 nightly
$110 total
Sep 29 - Sep 30
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

6. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Jesse
$147 nightly
$167 total
Oct 26 - Oct 27
Total with taxes and fees
Graduate by Hilton Annapolis
A waterfront hotel with multiple floors, a marina with boats, and a cityscape in the background.
A grand staircase with a wooden finish and a curved design, leading to an upper level.
A luxurious room with a large chandelier, three arched windows with curtains, and two round tables with benches.
A hotel room with a large arched window offering a view of a cityscape at night.

7. The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore
Otterbein
United States
Andrea
$152 nightly
$179 total
Sep 27 - Sep 28
Total with taxes and fees
The Royal Sonesta Harbor Court Baltimore
A modern lobby with a seating area, a fireplace, and a bookshelf.
A restaurant with a yellow cushioned bench, wooden tables, and chairs.
A modern hotel room with a flat-screen TV, a sofa, a chair, and a small table.
A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

8. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
JOANA JENNIFER
$130 nightly
$149 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown
An outdoor bar area with tables and chairs, a view of the water, and buildings in the background.
A spacious hotel lobby with multiple seating areas, a central staircase, and a large open space with a view of the lobby.
A lobby with a green sofa, a purple ottoman, and a patterned armchair. There is a reception desk with a large painting above it.
A large indoor venue with tables set for dining, large windows, and a view of the water.

9. Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore
Inner Harbor
United States
Scott
$106 nightly
$124 total
Sep 29 - Sep 30
Total with taxes and fees
Pier 5 Hotel Baltimore
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Bobbi
$199 nightly
$227 total
Oct 25 - Oct 26
Total with taxes and fees
The Westin Annapolis
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A modern lobby with a reception desk, seating area, and a patterned rug.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.

11. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Jessica
$97 nightly
$110 total
Sep 27 - Sep 28
Total with taxes and fees
Sonesta ES Suites Annapolis
A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.
A modern kitchen with a bar area, wooden flooring, and blue bar stools.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

12. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Patty
$229 nightly
$261 total
Sep 30 - Oct 1
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
A balcony with a table set for two, overlooking a marina with boats.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.

13. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
Karen
$271 nightly
$309 total
Oct 12 - Oct 13
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

14. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
joe
$114 nightly
$129 total
Oct 4 - Oct 5
Total with taxes and fees
Courtyard by Marriott Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A multi-story hotel with a brick facade, large windows, and an American flag.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

15. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Sterling
$110 nightly
$125 total
Sep 30 - Oct 1
Total with taxes and fees
Crowne Plaza Annapolis by IHG
A modern indoor pool area with lounge chairs, a glass wall, and a skylight.
A modern outdoor patio with seating and umbrellas, a glass wall, and a view of the sky.
A city skyline with modern buildings, a marina with boats, and a well-lit waterfront area.
A hotel room with a large bed, a sofa, a desk, and a view of the city through large windows.

16. Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor
Harbor East
United States
Edrick
$135 nightly
$159 total
Oct 18 - Oct 19
Total with taxes and fees
Hyatt Place Baltimore Inner Harbor
A modern indoor swimming pool with lounge areas and large windows.
A restaurant interior with wooden beams, round tables, and hanging pendant lights.
A hotel with a central fountain, a brick facade, and a sign reading "The Hotel".
A spacious lobby with a fireplace, comfortable seating, and a staircase.

17. The Hotel at Arundel Preserve

The Hotel at Arundel Preserve
Arundel Mills
United States
Kristin
$126 nightly
$144 total
Oct 12 - Oct 13
Total with taxes and fees
The Hotel at Arundel Preserve
A hotel entrance with a large illuminated sign reading "a loft W Hotels".
A modern lounge area with sofas, tables, and hanging lamps.
An outdoor patio area with modern seating, umbrellas, and a building with large windows.
An outdoor seating area with green and black furniture, a pool, and a modern building with large windows and a blue ceiling.

18. Aloft by Marriott BWI Baltimore Washington International Airport

Aloft by Marriott BWI Baltimore Washington International Airport
Linthicum Heights
United States
Octavio
$89 nightly
$102 total
Oct 4 - Oct 5
Total with taxes and fees
Aloft by Marriott BWI Baltimore Washington International Airport
A room with a pool, two sofas, a table, and a patterned rug.
A modern kitchen with wooden cabinets, a white countertop, and various food items displayed.
A hotel reception area with a wooden reception desk, teal chairs, and a patterned rug.
A modern hotel room with a bed, sofa, coffee table, TV, and a minibar.

19. Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East
Upper Marlboro
United States
Zina
$87 nightly
$99 total
Oct 18 - Oct 19
Total with taxes and fees
Comfort Inn Largo-Washington DC East
A hotel entrance with a covered walkway, a green van parked outside, and a clear sky.
A bathroom with a bathtub, a bench, and a wall-mounted TV.
A hotel room with a large flat-screen TV, a desk with a lamp, a chair, a bench, and a window with curtains.
A hotel room with two beds, a desk, a chair, a TV, and a window with blinds.

20. Holiday Inn Washington-College Pk (I-95) by IHG

Holiday Inn Washington-College Pk (I-95) by IHG
College Park
United States
Pierre
$91 nightly
$103 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Washington-College Pk (I-95) by IHG
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Where to stay near Shady Side

Shady Side offers a charming blend of outdoor activities and family-friendly attractions. Explore nearby areas for a relaxing atmosphere filled with friendly locals, historical sites, and beautiful scenery. It's the perfect destination for those seeking a memorable vacation experience.
A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.
A row of historic buildings with a prominent steeple and American flag.
A red brick building with a white dome and a flag on top.
A brick building with a sign reading "Maryland Inn" and an American flag.
A waterfront with a speedboat, a white bus, and a historic building with a dome in the background.

Annapolis

Annapolis is the ultimate destination for travelers seeking a blend of outdoor adventure and city charm. Here, you can explore the stunning Chesapeake Bay Bridge, relax at Sandy Point State Park, or delve into maritime history at the Annapolis Maritime Museum. With its vibrant shopping centers and a welcoming atmosphere, Annapolis makes for a great base, located about 18 miles by car from Shady Side. Choosing Annapolis for your stay ensures a memorable experience filled with diverse activities and attractions.

Vintage military aircraft parked on an airfield.
A historic fort with a large gate, a flagpole, and a grassy hill.
A wooden bridge surrounded by trees.
The Washington Monument reflected in water, surrounded by cherry blossoms.
A large church with a prominent steeple, surrounded by green lawns and a parking lot.

Upper Marlboro

Experience the charm of Upper Marlboro, an excellent hub for families and weekend getaway travelers looking for a blend of city and outdoor adventures. With attractions like the National Mall, the Smithsonian Institution, and the Show Place Arena nearby, visitors can enjoy a variety of activities from shopping to sports. Located about 18 miles by car from Shady Side, Upper Marlboro offers a strategic base to explore the area while providing a welcoming atmosphere for all.

Galesville

Make your vacation planning effortless by staying in Galesville, a haven for families and nature enthusiasts thanks to its access to outdoor adventures and scenic beauty. You’ll love exploring the nearby Shadyside Park, visiting the historic London Town, and relaxing at Triton Beach, all adding to the charm of this quaint area. Located about 2 miles by car from Shady Side, Galesville is a smart choice for a memorable getaway.

Beverly Beach

Beverly Beach stands out as a prime spot for families and nature enthusiasts interested in exploring serene beaches and vibrant outdoor activities. Nestled near attractions like Triton Beach and the Maryland Quiet Waters Park, visitors can enjoy sun-soaked days and scenic nature trails. The Annapolis Maritime Museum offers an educational experience for all ages. Located about 20 miles by car from Shady Side, Beverly Beach makes for a smart choice for travelers seeking a relaxing getaway immersed in nature's beauty.

Churchton

Travelers seeking a family-friendly getaway will find Churchton to be an ideal base for their vacation, featuring beautiful outdoor spaces and scenic beaches. With attractions like Shadyside Park, Franklin Point State Park, and Triton Beach, visitors can immerse themselves in nature and enjoy various recreational activities. Located about 3 miles by car from Shady Side, Churchton offers a peaceful retreat that's perfect for a relaxing stay. It's a smart choice for your next vacation, blending convenience and natural beauty.

Stay near popular attractions in and around Shady Side

Shady Side invites travelers to immerse themselves in its charming outdoor scenery, perfect for family vacations. With lush parks, serene marinas, and intriguing historic homes, there's a delightful blend of culture and nature waiting to be explored in this picturesque destination.
A beach with rocky outcrops, trees, and calm water under a partly cloudy sky.

Triton Beach

8.0/10 (6 reviews)
Often cited as a favorite among beachgoers, Triton Beach offers inviting sandy shores and a relaxed atmosphere perfect for a day of sun and fun. Located about 20 miles by car from Shady Side, it provides easy access for a refreshing escape, making it a convenient spot to unwind and enjoy the beach vibes.
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A forested area with a winding road.

Maryland Quiet Waters Park

8.4/10 (49 reviews)
Ideal for travelers interested in a serene escape, Maryland Quiet Waters Park offers a tranquil blend of nature and art with scenic trails and beautiful landscapes. Located about 26 miles by car from Shady Side, it's a convenient spot to explore outdoor activities and unwind in a peaceful setting.
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A beach with two people, a large suspension bridge in the background.

Chesapeake Bay Bridge

8.8/10 (1,066 reviews)
Perfectly suited for road trippers, the Chesapeake Bay Bridge offers stunning views and a vibrant atmosphere. Spanning the Chesapeake Bay, this modern bridge is about a 33-mile drive from Shady Side. Staying nearby lets you easily explore this iconic landmark and the surrounding attractions.
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Shadyside Park

Set the stage for your family adventure at Shadyside Park, a vibrant urban park in Shady Side, Maryland. Enjoy outdoor activities amid the city's lively atmosphere, perfect for creating cherished memories. With its convenient location, Shadyside Park offers easy access to local amenities, making it an ideal spot for your stay.
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Annapolis Maritime Museum

9.0/10 (27 reviews)
No trip is complete without a visit to the Annapolis Maritime Museum, ideal for culture seekers exploring Maryland's rich maritime heritage. Experience engaging exhibits and beautiful waterfront views, all about 19 miles by car from Shady Side. Staying nearby offers easy access to this unique cultural gem.
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London Town

8.4/10 (8 reviews)
Discover the appeal of this historic site, London Town, ideal for culture seekers and history buffs. With its rich heritage and vibrant atmosphere, visitors can immerse themselves in the past. It’s about an 18-mile drive from Shady Side, making it a convenient stop for a day trip filled with exploration.
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Captain Avery Museum

A fascinating mix of history and culture, the Captain Avery Museum in Shady Side, Maryland, offers a glimpse into the maritime heritage of the region. This historic house showcases unique exhibits that celebrate local traditions and stories. Being located within Shady Side makes it easy to explore the surrounding area, enhancing your visit.
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Galesville Heritage Museum

A must-see for history buffs, Galesville Heritage Museum offers a captivating glimpse into the area's rich cultural heritage. Located about 2 miles from Shady Side, this inviting spot showcases local history and unique exhibits, making it easy to explore nearby while enjoying your stay in the region.
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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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The room was perfect. The location was amazing!"
Nicole 1-night trip
Posted 7 hours ago
Historic Inns of Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"The St. Michaels Inn is a great location and value! It's an older property, but it was clean, safe, and comfortable. I wouldn't hesitate to book again."
Elisa 4-night trip
Posted 15 hours ago
St Michaels Inn
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I liked the staff!"
Elliott 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"it was good for the price."
Tonya Lynn 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

8/10 Good
"Staff was ok."
Naqibullah 8-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Largo/Washington DC
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Staff and xkean roo."
Thomas 2-night trip
Posted 3 days ago
Comfort Inn Largo-Washington DC East
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."
Karen 3-night trip
Posted 4 days ago
Annapolis Waterfront Hotel, Autograph Collection
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."
William 1-night trip
Posted 4 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 4 days ago
The Westin Annapolis

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
$78 nightly
$89 total
Oct 4 - Oct 5
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Best Western Annapolis
Microtel Inn & Suites by Wyndham Gambrills/Odenton

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD
$93 nightly
$107 total
Oct 12 - Oct 13
Total with taxes and fees
Microtel Inn & Suites by Wyndham Gambrills/Odenton
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
$99 nightly
$109 total
Oct 4 - Oct 5
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
$101 nightly
$115 total
Sep 30 - Oct 1
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
$109 nightly
$123 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn Conference Center
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
$127 nightly
$141 total
Oct 4 - Oct 5
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Best Western Kent Narrows Inn

Hotels in Shady Side with star-rating

Find out more about Shady Side

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.

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

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.

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 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.

Frequently asked questions

What is the best area to stay in Shady Side?
The best area to stay in Shady Side is along the waterfront, particularly near the marinas and the mouth of the West River.This area offers direct access to the Chesapeake Bay and West River, providing a scenic backdrop for your stay. You'll find many properties with water views, private docks, and outdoor spaces superb for enjoying the coastal environment. The general layout is residential, with properties spread out along the shoreline and smaller roads leading to the water.Couples looking for a relaxing getaway will appreciate the tranquility and natural beauty of the waterfront. Many accommodations here offer private settings, ideal for unwinding, enjoying sunsets over the water, and perhaps even engaging in water-based activities like kayaking or paddleboarding directly from their rental.Families will also find the waterfront appealing due to the spacious properties and opportunities for outdoor recreation. Children can enjoy exploring the shoreline, and many homes come equipped with amenities like private pools or yards, offering plenty of space for activities.
When is the best time to go to Shady Side?
The best time to go to Shady Side is during the late spring (May to early June) and early autumn (September to October) for the most pleasant weather.During these months, the temperatures are mild, typically ranging from the 60s to high 70s Fahrenheit, making it ideal for outdoor activities without the humidity of summer or the chill of winter. This period is great for couples or solo travelers looking for a comfortable and tranquil getaway, as they can enjoy waterfront dining and exploring the local parks without large crowds.Summer, from mid-June to August, is also a popular time, especially for families. While it can be warmer and more humid, with temperatures often in the 80s, this is when all water-based activities are in full swing.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shady Side.
How much is the nightly rate at a Shady Side hotel?
Prices for hotels in Shady Side often vary, but you can find a great deal from $89 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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