Shady Side Hotels

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Our top choices for Shady Side hotels

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,003 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is P5,438
P6,037 total
includes taxes & fees
Mar 1 - Mar 2
Best Western Kent Narrows Inn

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1,003 reviews)
"Yes the room was clean and the staff was great "
United States
Thurnell
The price is P5,887
P7,692 total
includes taxes & fees
Feb 26 - Feb 27
Rod 'N' Reel Resort

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (476 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is P7,759
P8,846 total
includes taxes & fees
Feb 22 - Feb 23
Anchored Inn at Hidden Harbour Marina

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (370 reviews)
"Clean room, helpful staff, nice breakfast, beautiful views, excellent location."
United States
Denise
The price is P5,786
P6,365 total
includes taxes & fees
Feb 26 - Feb 27
Knapps Narrows Marina & Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,001 reviews)
"Good value and close to downtown."
United States
John
St Michaels Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (875 reviews)
"Nice staff and rooms"
United States
Walter
The price is P4,869
P5,405 total
includes taxes & fees
Mar 16 - Mar 17
Quality Inn Grasonville near Kent Island

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (131 reviews)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is P8,621
P9,484 total
includes taxes & fees
Feb 23 - Feb 24
Parsonage Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (92 reviews)
"We were"
United States
Guevara
The price is P7,354
P10,635 total
includes taxes & fees
Mar 11 - Mar 12
Wylder Tilghman Island

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1,016 reviews)
"Great staff & clean rooms. "
United States
Carmelo
The price is P4,918
P5,607 total
includes taxes & fees
Mar 8 - Mar 9
Microtel Inn & Suites by Wyndham Gambrills

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (67 reviews)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is P9,779
P10,757 total
includes taxes & fees
Mar 4 - Mar 5
George Brooks House B&B

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is P6,595
P7,321 total
includes taxes & fees
Feb 24 - Feb 25
Hilton Garden Inn Kent Island Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is P8,969
P9,865 total
includes taxes & fees
Feb 21 - Feb 22
The Tilghman Island Inn

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
The price is P10,363
P12,672 total
includes taxes & fees
Mar 1 - Mar 2
The Wildset

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,002 reviews)
"Quiet lodging, great location "
United States
Daniel
The price is P5,728
P6,473 total
includes taxes & fees
Feb 23 - Feb 24
Comfort Inn Conference Center

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (961 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is P5,508
P6,114 total
includes taxes & fees
Mar 8 - Mar 9
Holiday Inn Express Annapolis East-Kent Island by IHG

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (717 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is P6,712
P7,450 total
includes taxes & fees
Mar 3 - Mar 4
Hyatt Place Kent Narrows & Marina

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is P4,804
P5,477 total
includes taxes & fees
Mar 8 - Mar 9
DoubleTree by Hilton Hotel Annapolis

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (208 reviews)
"Hotel was clean staff was friendly"
United States
Kim
The price is P4,362
P4,973 total
includes taxes & fees
Mar 15 - Mar 16
Candlewood Suites Annapolis by IHG

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (178 reviews)
"Room was very nice and clean. Only thing that needs to change is the parking situation. They need more parking spaces. And they charge $30 for parking. "
United States
Cecilia
The price is P6,365
P7,256 total
includes taxes & fees
Feb 25 - Feb 26
Fairfield Inn & Suites By Marriott Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Shady Side attractions

Top Shady Side Hotel Reviews

More cheap stays in Shady Side

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 Largo/Washington DC, located 18.8 mi (30.3 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 La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and Sonesta ES Suites Annapolis. 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?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and Sonesta ES Suites Annapolis 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.