Shady Side Hotels

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Our top choices for Shady Side hotels

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
Experience serene stays at this peaceful inn with seasonal outdoor pool and garden terrace. Located conveniently near Saint Michaels Village and Classic Motor Museum, guests appreciate the helpful staff, clean rooms, and complimentary breakfast, WiFi, and parking.

"Good value and close to downtown."
United States
John
The price is P5,920
P6,512 total
includes taxes & fees
Jan 11 - Jan 12
St Michaels Inn

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, (947)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available onsite. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Center after a quiet night's rest.

"It was very comfortable and clean"
United States
Maria
The price is P5,121
P5,684 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1008)
"Yes, everything was spot on. Do come and stay at the Rod and Reel for any special occassion. You will be glad you can."
United States
Alfred
The price is P5,359
P7,125 total
includes taxes & fees
Jan 11 - Jan 12
Rod 'N' Reel Resort

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1005)
"Great hospitality and breakfast was good…"
United States
Martha
The price is P4,238
P4,831 total
includes taxes & fees
Jan 10 - Jan 11
Best Western Annapolis

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
Experience Art Deco style at this downtown Annapolis hotel, just minutes from the U.S. Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness center.

"Great value for stay with breakfast included "
United States
Aisling
The price is P5,406
P6,163 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Annapolis Downtown

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
Located just 5 minutes from U.S. Naval Academy, this hotel offers convenient access to Annapolis Harbor Center and Westfield Annapolis Mall. Enjoy the 24-hour fitness center, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.

"Great stay "
United States
Jose Miguel
The price is P4,875
P5,557 total
includes taxes & fees
Jan 11 - Jan 12
DoubleTree by Hilton Hotel Annapolis

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1003)
Just steps from Prince George's Stadium, this tranquil retreat offers free breakfast, WiFi and parking. Guests love the quiet atmosphere and convenient location near shopping and dining options. The 24-hour fitness center and American cuisine at Chessies Chesapeake Grill complete your relaxing stay.

"The staff was amazing , very friendly. Rooms were very clean."
United States
Victoria
The price is P5,768
P6,518 total
includes taxes & fees
Feb 2 - Feb 3
Comfort Inn Conference Center

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is P4,662
P5,315 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1006)
Just 10 minutes from the U.S. Naval Academy, this serene hotel offers free parking and WiFi. Unwind in the indoor pool and hot tub after exploring nearby Westfield Annapolis Mall and local restaurants. Guests consistently praise the peaceful atmosphere and attentive staff.

"Breakfast menu was great! Pool and hot tub were nice!"
United States
Terrence
The price is P5,693
P6,490 total
includes taxes & fees
Jan 8 - Jan 9
Country Inn & Suites by Radisson, Annapolis, MD

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1003)
Just a 5-minute drive from U.S. Naval Academy, this hotel offers a calm atmosphere with comfortable beds and helpful staff. Enjoy Trophy Room for dinner, a bar/lounge, and complimentary bike rentals to explore nearby attractions and dining options.

"Pleasant staff. Good location to walk to restaurants, shops. "
United States
Beth
The price is P8,640
P9,849 total
includes taxes & fees
Jan 11 - Jan 12
Graduate by Hilton Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1908)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness center and garden terrace. Just a short walk from the U.S. Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.

" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1003)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the U.S. Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness center. Located within easy walking distance to restaurants and shops.

"Clean room and friendly staff! "
United States
Silvia
The price is P4,709
P5,368 total
includes taxes & fees
Jan 10 - Jan 11
Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1010)
Located within a 10-minute drive of U.S. Naval Academy, this hotel offers a seasonal outdoor pool and fitness center. Guests praise the helpful staff and free breakfast. Annapolis Harbor Center Shopping Center is nearby for all your needs.

"Appreciated that it was in a quiet area. Great hospitality! Will stay again when visiting Maryland."
United States
robin
The price is P5,261
P5,998 total
includes taxes & fees
Jan 12 - Jan 13
Hampton Inn & Suites Annapolis

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1004)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Center.

"Nice place "
United States
Tucker T
The price is P4,910
P5,450 total
includes taxes & fees
Jan 11 - Jan 12
Best Western Kent Narrows Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links for easy exploration.

"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is P4,953
P5,498 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (693)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Center and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.

"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is P6,828
P7,579 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is P7,531
P10,426 total
includes taxes & fees
Jan 6 - Jan 7
Kent Island Resort

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1004)
Situated just a short drive from the U.S. Naval Academy, this hotel offers American cuisine at The Bistro. Guests praise the peaceful atmosphere, helpful staff, and clean rooms. Free WiFi and parking enhance your stay near Annapolis Harbor Center.

"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is P4,944
P5,637 total
includes taxes & fees
Jan 25 - Jan 26
Courtyard by Marriott Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
Discover peaceful luxury in Annapolis with a full-service spa offering massages and facials. After enjoying Captain's Daughter restaurant, take a refreshing dip in the indoor pool or maintain your workout routine at the 24-hour fitness center.

"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is P8,182
P9,327 total
includes taxes & fees
Jan 6 - Jan 7
The Westin Annapolis

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (364)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.

"nice clean room staff very nice would stay again "
United States
mario
The price is P5,886
P6,475 total
includes taxes & fees
Jan 6 - Jan 7
Knapps Narrows Marina & Inn
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 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 DoubleTree by Hilton Hotel Largo/Washington DC and Historic Inns of 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. Offers free self parking, an indoor pool, and a 24-hour fitness center. Crowne Plaza Annapolis by IHG and La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 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 14 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 Franklin Point State Park and Captain Avery Museum. 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.