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

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12 Aug - 13 Aug
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13 Aug - 14 Aug
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14 Aug - 16 Aug
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21 Aug - 23 Aug

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Our top choices for Shady Side hotels

1. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Dale
AED 740
AED 844 total
includes taxes & fees
7 Sep - 8 Sep
Anchored Inn at Hidden Harbour Marina

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
AED 1,289
AED 1,469 total
includes taxes & fees
25 Aug - 26 Aug
The Inn at Tacaro Estate

3. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
AED 437
AED 498 total
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites by Marriott Annapolis

4. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Javier
AED 360
AED 428 total
includes taxes & fees
23 Aug - 24 Aug
Candlewood Suites Annapolis by IHG

5. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
Jessica
AED 621
AED 708 total
includes taxes & fees
16 Aug - 17 Aug
The Westin Annapolis

6. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Audrey
AED 364
AED 415 total
includes taxes & fees
2 Sep - 3 Sep
Sonesta ES Suites Annapolis

7. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
Stacey
AED 761
AED 868 total
includes taxes & fees
7 Sep - 8 Sep
Annapolis Waterfront Hotel, Autograph Collection

8. 1313 West Luxury Boutique Hotel

1313 West Luxury Boutique Hotel
Homewood
AED 1,076
AED 1,227 total
includes taxes & fees
19 Aug - 20 Aug
1313 West Luxury Boutique Hotel

9. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
Nelson
AED 366
AED 418 total
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Annapolis Downtown

10. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Patricia
AED 479
AED 546 total
includes taxes & fees
23 Aug - 24 Aug
Graduate by Hilton Annapolis

11. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Meghalee
AED 358
AED 409 total
includes taxes & fees
19 Aug - 20 Aug
Hampton Inn & Suites Annapolis

12. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
Annapolis
United States
Jamila
AED 404
AED 461 total
includes taxes & fees
19 Aug - 20 Aug
TownePlace Suites by Marriott Annapolis

13. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
AED 358
AED 409 total
includes taxes & fees
25 Aug - 26 Aug
Hilton Garden Inn Annapolis

14. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
Annapolis
United States
Caitlin
AED 496
AED 565 total
includes taxes & fees
23 Aug - 24 Aug
Residence Inn By Marriott Annapolis

15. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Tyriek
AED 353
AED 402 total
includes taxes & fees
7 Sep - 8 Sep
Courtyard by Marriott Annapolis

16. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Eileen
AED 433
AED 494 total
includes taxes & fees
16 Aug - 17 Aug
Fairfield Inn & Suites By Marriott Annapolis

17. 134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
Annapolis
United States
Chris
AED 783
AED 893 total
includes taxes & fees
17 Aug - 18 Aug
134 Prince - Luxury Boutique Hotel

18. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
AED 337
AED 510 total
includes taxes & fees
25 Aug - 26 Aug
Historic Inns of Annapolis

19. Flag House Inn

Flag House Inn
Historic District
United States
Tyler
AED 835
AED 951 total
includes taxes & fees
16 Aug - 17 Aug
Flag House Inn

20. 86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
Historic District
Norway
Jo
AED 1,470
AED 1,676 total
includes taxes & fees
18 Aug - 19 Aug
86 State Circle - Luxury Boutique Hotel
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Stay near popular Shady Side attractions

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
See properties

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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"I wish breakfast would have included yogurt and a better variety of cereals. Cookies at front desk were delicious and appreciated."
Richard 1-night trip
Posted less than an hour ago
Country Inn & Suites by Radisson, Annapolis, MD
Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Staff was lovely and the location can’t be beat. The Maryland Inn building is old, and some of the elements are thus seemingly harder to clean (ie if you’re weird about bathrooms being spotless, this one isn’t for you)."
Anya 2-night trip
Posted 1 hour ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"It was great!! Great bed, very clean, great bar and breakfast and all around excellent staff."
Liana 1-night trip
Posted 22 hours ago
DoubleTree by Hilton Hotel Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Comfortable bed. Very clean"
Anne 1-night trip
Posted 22 hours ago
Hilton Garden Inn Annapolis Downtown
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Smelled really nice muahahaha"
August 1-night trip
Posted 1 day ago
Comfort Inn Conference Center
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Location, staff and cleanliness were above and beyond!"
Patricia 4-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"We enjoyed our stay. Rooms were clean and the staff were very friendly. Looking forward to our next visit to St Michael’s. We would definitely stay here again."
Lori 2-night trip
Posted 2 days ago
St Michaels Inn
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Great"
Ogenna 2-night trip
Posted 3 days ago
Comfort Inn Largo-Washington DC East
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

10/10 Excellent
"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."
Sandra 3-night trip
Posted 3 days ago
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

More cheap stays in Shady Side

WoodSpring Suites Washington DC East Arena Drive

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD
AED 290
AED 328 total
16 Aug - 17 Aug
includes taxes & fees
WoodSpring Suites Washington DC East Arena Drive
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
AED 314
AED 346 total
31 Aug - 1 Sep
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
St Michaels Inn
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
AED 353
AED 402 total
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,135 reviews)
Microtel Inn & Suites by Wyndham Gambrills
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
AED 358
AED 409 total
19 Aug - 20 Aug
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
AED 371
AED 423 total
18 Aug - 19 Aug
includes taxes & 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
AED 437
AED 494 total
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Comfort Inn Conference Center

Find out more about Shady Side

Top reasons to visit Shady Side

  • Outdoor Activities: Shady Side is perfect for nature lovers, offering scenic marinas and urban parks for various recreational activities.
  • Family-Friendly Attractions: The area caters to families with fun experiences and educational opportunities for all ages.
  • Proximity to Annapolis: Just a short drive away, visitors can explore the vibrant downtown of Annapolis for dining and shopping.
  • Charming Accommodations: Enjoy a range of lodging options, from cozy bed & breakfasts to comfortable hotels.
  • Welcoming Atmosphere: Experience the friendly vibes of the locals while enjoying Shady Side's peaceful charm.

Find great hotels near Shady Side

Shady Side, Maryland, offers a delightful selection of accommodations, from charming bed & breakfasts to comfortable hotels. Whether you're seeking a pet-friendly stay, a business-friendly environment, or an LGBTQIA welcoming atmosphere, you'll find a range of options tailored to your needs. Explore the best hotels in the area and enjoy a memorable vacation experience with easy access to nearby attractions and scenic views.

  • Country Inn & Suites by Radisson, Annapolis, MD: Experience a warm and inviting atmosphere at Country Inn & Suites by Radisson, Annapolis. This 3-star hotel, located 16.1km from Shady Side, is perfect for travelers seeking a pet-friendly, LGBTQIA-welcoming space. Guests can enjoy the comforts of home with amenities tailored for business and leisure travelers alike. The hotel features a dog exercise area and a flexible pet policy, ensuring that your furry friends feel at home. With an emphasis on inclusivity and comfort, this hotel makes every visitor feel welcome.
  • Comfort Inn Conference Center: Ideal for families and business travelers alike, the Comfort Inn Conference Center is situated 20.9km from Shady Side. This hotel provides a friendly environment where children can thrive, featuring amenities such as a secure pool area. Pet-friendly accommodations ensure that your pets are welcome too, with a waived fee for service animals. With comfortable rooms and convenient access to local attractions, this property strikes a balance between family fun and business efficiency, making it a versatile choice for your stay.
  • Historic Inns of Annapolis: Step back in time at the Historic Inns of Annapolis, a 3.5-star hotel located 16.1km from Shady Side. Nestled in a national historic building, this hotel offers a unique blend of adventure and rich history. Guests can partake in nearby activities such as hiking, sailing, and kayaking, making it perfect for those seeking outdoor excitement. With a distinguished ambiance and a commitment to providing memorable experiences, this hotel is ideal for history buffs and adventure seekers alike.

Where to stay near Shady Side

Shady Side, Maryland, is the perfect destination for those seeking a family-friendly getaway amidst stunning scenery. Enjoy the peaceful atmosphere while exploring nearby attractions like vibrant downtown Annapolis, just a few miles away. Experience the charm of this quiet location, ideal for outdoor adventures and relaxing escapes, all while soaking in the welcoming vibes of friendly locals and beautiful surroundings. Shady Side promises a memorable experience for every traveler.

  • Annapolis: Located 16.1km from Shady Side, Annapolis is a vibrant city known for its rich history and stunning waterfront. Visitors flock to this charming destination year-round, with peak travel months from June to August. Annapolis offers a delightful mix of family-friendly activities, business opportunities, and urban exploration. Key highlights include the U.S. Naval Academy, picturesque beaches, and an array of shopping centers that cater to all tastes. Whether you're strolling through the historic district or enjoying the lively tourist precinct, Annapolis promises a memorable experience.
  • Galesville: Just 3.2km from Shady Side, Galesville is a quaint town that offers a perfect blend of outdoor adventure and scenic beauty. With moderate seasonality in visitor arrivals, the peak season from June to August invites travelers seeking a romantic getaway or outdoor fun. Galesville boasts charming recreational areas, educational sites, and shopping centers. Nature enthusiasts will love the nearby lake, beautiful beaches, and serene urban parks, making it an ideal spot for relaxation and exploration.
  • Churchton: Located 4.8km from Shady Side, Churchton is a picturesque city that draws visitors for its stunning outdoor landscapes and romantic ambiance. Travel peaks during the months of February, June to July, and October, offering a seasonal escape for nature lovers. With access to recreational areas, a scenic boardwalk, and educational facilities, Churchton is perfect for those who appreciate the great outdoors. Attractions such as the nearby lake, inviting beaches, and the expansive national state park provide ample opportunities for adventure and relaxation.

Things to do near Shady Side

Shady Side, Maryland, is perfect for outdoor family vacations, offering a variety of scenic activities. Visitors can enjoy the recreational areas, explore educational opportunities, and shop at local centers. It's an ideal destination for those looking to relax and connect with nature while engaging in fun activities with loved ones.

Shopping

If you're up for a drive, visit the Westfield Annapolis Mall, 16.1km away, for a variety of shops and entertainment. Closer to Shady Side, explore the Wild Bird Center, 12.9km away, or the Annapolis Harbor Center Shopping Center, 14.5km away, both offering family-friendly vibes.

Recreation

Navy-Marine Corps Memorial Stadium offers an energetic atmosphere for sports enthusiasts, just 16.1km from Shady Side. South River Golf Links, located 9.7km away, provides a scenic outdoor golf experience. For a touch of luxury, visit the Old South Country Club, situated 12.9km from town.

Adventure

Experience the thrill at Chesapeake Beach Water Park, where you can enjoy thrilling slides and family-friendly attractions, located 16.1km from Shady Side. For water sports enthusiasts, Annapolis Sailing School offers exciting sailing lessons 14.5km away. Explore the scenic St Michaels Nature Trail, 25.7km away, for a refreshing outdoor adventure.

Nightlife

Experience a vibrant nightlife in Shady Side with a visit to The Colonial Players for captivating theater performances. For family fun, check out Annapolis Bowl or Crofton Bowl, both offering exciting arcade adventures and a lively atmosphere perfect for all ages.

*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 from December to February when prices drop, especially on Mondays, the least expensive day to stay. Use Expedia’s search tool to filter your hotel options by budget and book a package that combines hotel, flights, and activities for additional savings. Look for flexible booking options and take advantage of good deals for great rates. For transportation, explore local public transport options, or enjoy the area on foot to keep costs down while discovering the scenic beauty of 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 choices based on your budget, desired location, and preferred hotel type. 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 Shady Side hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in and around Shady Side

Shady Side, Maryland, offers a delightful blend of outdoor activities and family-friendly attractions. Visitors can explore scenic marinas, historic houses, and urban parks, making it an ideal destination for those seeking cultural experiences and natural beauty. Whether you’re interested in boating, history, or simply enjoying the great outdoors, Shady Side has something for everyone to enjoy during their vacation.

  • U.S. Naval Academy: Located 16.1km from Shady Side, the U.S. Naval Academy offers a unique glimpse into American naval history. Stroll through its picturesque campus, marvel at the stunning architecture, and enjoy scenic views along the waterfront.
  • Shadyside Park: Situated right in Shady Side, this urban park is perfect for families and outdoor enthusiasts. With playgrounds, picnic areas, and walking trails, it provides a refreshing escape in a vibrant city setting.
  • Galesville Heritage Museum: Just 3.2km away, this charming history museum showcases the rich culture of Galesville. Explore exhibits that highlight local heritage and learn about the area's fascinating past.

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

To reach Shady Side, Maryland, you can fly into three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is situated 45.1km away, with luxury hotels like Salamander Washington DC and Riggs Washington DC, both within 4.8km, offering convenient access. Washington, DC (IAD-Washington Dulles Intl.) is 82.1km from Shady Side, featuring hotels such as the 4-star Hyatt Regency Dulles and Hilton Washington Dulles Airport, both within 3.2km. Lastly, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is only 40.2km away, with the 5-star Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore located 12.9km from the airport, providing various transportation options.

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 Historic Inns of Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Shady Side.
What are some of the best vacation rentals that Shady Side has to offer?
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Shady Side vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. See all 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.
Where can I learn more about changing or cancelling my trip to Shady Side?
To find more details about updating your trip to Shady Side or cancelling it, click here.
Where is the best hotel to stay near Shadyside Park?
Anchored Inn at Hidden Harbour Marina is one of the top choices for your stay based on our traveler data, and this hotel offers an outdoor pool and free parking. It's located 4.8 mi (7.7 km) from Shadyside Park.
What about the best place to stay near Captain Avery Museum?
One of the top choices for your stay is Anchored Inn at Hidden Harbour Marina, located 5 mi (8.1 km) from Captain Avery Museum, and this hotel offers an outdoor pool and free parking.
What are some accommodations with pools in Shady Side?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and St Michaels Inn are two additional hotels that offer an onsite pool. View all hotels with pools in Shady Side.
What's the best place to stay near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
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 16 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.