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

Find hotels in Shady Side, MD from ₩123,714

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Filter by

Star rating

Guest rating

Our top choices for Shady Side hotels

1. Laurel Grove Inn on the South

Laurel Grove Inn on the South
Annapolis
United States
Ruth
₩249,449
₩284,372 total
includes taxes & fees
Sep 7 - Sep 8
Laurel Grove Inn on the South

2. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Rachel
₩165,946
₩187,519 total
includes taxes & fees
Aug 23 - Aug 24
Comfort Inn Conference Center

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Fabiana
₩136,075
₩155,125 total
includes taxes & fees
Aug 30 - Aug 31
DoubleTree by Hilton Hotel Annapolis

4. Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC
Lanham
United States
Jeffrey
₩146,593
₩165,651 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Glenarden/Washington DC

5. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Karen
₩124,250
₩136,674 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn

6. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
₩111,713
₩127,353 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Annapolis

7. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
Gambrills
United States
James
₩128,015
₩145,937 total
includes taxes & fees
Aug 30 - Aug 31
Microtel Inn & Suites by Wyndham Gambrills

8. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
₩129,179
₩194,956 total
includes taxes & fees
Aug 30 - Aug 31
Historic Inns of Annapolis

9. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
₩132,756
₩151,342 total
includes taxes & fees
Sep 13 - Sep 14
Country Inn & Suites by Radisson, Annapolis, MD

10. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
₩178,772
₩203,800 total
includes taxes & fees
Aug 26 - Aug 27
SpringHill Suites by Marriott Annapolis

11. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Heather
₩146,423
₩166,922 total
includes taxes & fees
Sep 7 - Sep 8
Crowne Plaza Annapolis by IHG

12. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
₩177,102
₩196,583 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Annapolis East-Kent Island by IHG

13. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
United States
Yolanda
₩185,840
₩210,000 total
includes taxes & fees
Aug 31 - Sep 1
Courtyard by Marriott Bowie

14. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
John
₩135,811
₩154,825 total
includes taxes & fees
Sep 22 - Sep 23
Sonesta ES Suites Annapolis

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
₩140,510
₩155,966 total
includes taxes & fees
Sep 14 - Sep 15
Quality Inn Grasonville near Kent Island

16. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
₩176,347
₩195,745 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Kent Narrows Inn

17. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
United States
BARBARA
₩209,175
₩230,093 total
includes taxes & fees
Aug 24 - Aug 25
Knapps Narrows Marina & Inn

18. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
₩232,882
₩258,499 total
includes taxes & fees
Sep 8 - Sep 9
Hyatt Place Kent Narrows & Marina

19. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Javier
₩135,811
₩161,670 total
includes taxes & fees
Sep 13 - Sep 14
Candlewood Suites Annapolis by IHG

20. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Meghalee
₩136,366
₩155,458 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Inn & Suites Annapolis
View all properties
Save an average of 15% on thousands of hotels when you're signed in

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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Very clean room, staff was very friendly and there are several restaurants right there. Oh, plus the casino!!"
Jennifer 1-night trip
Posted 1 hour ago
Rod 'N' Reel Resort
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great location nicely appointed room, great paintings"
Pauline 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great staff everywhere on the property."
Fabiana 1-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"A"
Wayne 1-night trip
Posted 7 hours ago
Country Inn & Suites by Radisson, Annapolis, MD
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Exceptional staff and services. They provided every amenity. The included daily breakfast was well prepared and staff stood at the ready to help and insure the area was kept clean and accessible asguests came and went. I would definitely recommend as well as use this location again."
Tommie 2-night trip
Posted 9 hours ago
Comfort Inn Conference Center
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"Perfect for what I needed"
Andrew 1-night trip
Posted 11 hours ago
Holiday Inn Express & Suites Annapolis by IHG
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 19 hours ago
Crowne Plaza Annapolis by IHG
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."
Erich 1-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."
Michael 3-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina

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
₩109,481
₩123,714 total
Aug 24 - Aug 25
includes taxes & fees
6/10 (1,007 reviews)
WoodSpring Suites Washington DC East Arena Drive
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
₩124,250
₩136,674 total
Aug 31 - Sep 1
includes taxes & fees
St Michaels Inn
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
₩128,015
₩145,937 total
Aug 30 - Aug 31
includes taxes & fees
9.2/10 Wonderful! (1,131 reviews)
Microtel Inn & Suites by Wyndham Gambrills
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
₩136,366
₩155,458 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,012 reviews)
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
₩139,969
₩159,565 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
₩165,946
₩187,519 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
Comfort Inn Conference Center

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.
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. Offers free self parking, an indoor pool, and complimentary wireless internet access. Rod 'N' Reel Resort 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 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.

Explore a world of travel with Expedia