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

Find hotels in Shady Side, MD from ļæ„12,634

  • 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

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Shady Side hotels

Free daily self-serve breakfast

1. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,003 reviews)
"The rooms were clean and modern, and my kids loved the pool. The breakfast was excellent, and we thoroughly enjoyed our stay"
United States
Zhun Wha
The price is ļæ„20,950
ļæ„23,883 total
includes taxes & fees
Jul 26 - Jul 27
SpringHill Suites by Marriott Annapolis
Lobby

2. Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC
2.5 star property
Lanham
9.2 out of 10, Wonderful, (1,001 reviews)
"Very nice stay."
United States
Favour
The price is ļæ„17,174
ļæ„19,407 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn & Suites Glenarden/Washington DC
Lobby

3. 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, (1,051 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is ļæ„19,358
ļæ„22,068 total
includes taxes & fees
Aug 17 - Aug 18
Country Inn & Suites by Radisson, Annapolis, MD
Reception

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,027 reviews)
"Good location, great room, and a great staff."
United States
Marie
The price is ļæ„19,274
ļæ„21,971 total
includes taxes & fees
Jul 26 - Jul 27
DoubleTree by Hilton Hotel Annapolis
Dinner served

5. Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,004 reviews)
"Room was good, staff was friendly and informative Breakfast was good Great parking available Good location, opposite a shopping mall"
United States
Rafael
The price is ļæ„17,807
ļæ„20,123 total
includes taxes & fees
Aug 10 - Aug 11
Comfort Inn Conference Center
Dining

6. Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,000 reviews)
"EXCELLENTE STAFF AND GREAT BREAKFAST..."
United States
Julian
The price is ļæ„13,887
ļæ„15,831 total
includes taxes & fees
Jul 30 - Jul 31
Best Western Annapolis
Property amenity

7. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
3.0 star property
Bowie
9.4 out of 10, Exceptional, (905 reviews)
"Stayed 2 nights with no complaints room was pretty clean, the grounds were clean and service was really goo"
United States
Carol
The price is ļæ„21,772
ļæ„24,603 total
includes taxes & fees
Aug 16 - Aug 17
Courtyard by Marriott Bowie
Indoor pool

8. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"Great place to stay for a short visit to Annapolis."
United States
Jeffrey
The price is ļæ„19,163
ļæ„21,846 total
includes taxes & fees
Aug 2 - Aug 3
Crowne Plaza Annapolis by IHG
Property amenity

9. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,005 reviews)
"Staff was very friendly, room was clean and comfy. All I ask!"
United States
Chris
The price is ļæ„20,950
ļæ„23,883 total
includes taxes & fees
Jul 20 - Jul 21
Courtyard by Marriott Annapolis
Meeting facility

10. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,882 reviews)
"Easy check in, easy valet, great location. Overall, very nice stay!"
United States
Caitlin
The price is ļæ„18,218
ļæ„26,322 total
includes taxes & fees
Jul 27 - Jul 28
Historic Inns of Annapolis
Exterior

11. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,107 reviews)
"Perfect for a weekend stay while going to the let's go music fest. Our 2nd year staying here"
United States
Erin
The price is ļæ„15,871
ļæ„18,092 total
includes taxes & fees
Aug 16 - Aug 17
Microtel Inn & Suites by Wyndham Gambrills
Lobby

12. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (280 reviews)
"Great stay in a quiet area"
United States
Mehran
The price is ļæ„14,702
ļæ„17,562 total
includes taxes & fees
Aug 2 - Aug 3
Candlewood Suites Annapolis by IHG
Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout drapes

13. 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, (1,000 reviews)
"Friendly staff"
United States
Keri
The price is ļæ„15,612
ļæ„17,797 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express & Suites Annapolis by IHG
Front of property

14. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,004 reviews)
"Great for the price"
United States
Ben
The price is ļæ„14,494
ļæ„15,943 total
includes taxes & fees
Jul 22 - Jul 23
St Michaels Inn
Lobby

15. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,003 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is ļæ„16,984
ļæ„19,362 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Annapolis
Front of property

16. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (493 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is ļæ„37,997
ļæ„43,316 total
includes taxes & fees
Aug 3 - Aug 4
Anchored Inn at Hidden Harbour Marina
Exterior

17. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1,000 reviews)
"Very nice hotel, great staff. Loved the convenient location."
United States
Marie
The price is ļæ„16,098
ļæ„18,352 total
includes taxes & fees
Aug 16 - Aug 17
Hampton Inn & Suites Annapolis
Superior Room, 1 King Bed, Accessible, Non Smoking (Roll-In Shower) | Bathroom | Towels

18. Red Roof Inn Annapolis

Red Roof Inn Annapolis
2.0 star property
Annapolis
7.2 out of 10, Good, (449 reviews)
"I am a repeat customer at this location. Staff is always personable and helpful."
United States
John
The price is ļæ„12,178
ļæ„13,883 total
includes taxes & fees
Jul 27 - Jul 28
Red Roof Inn Annapolis
King Jacuzzi Room | Desk, iron/ironing board, WiFi (free)

19. Executive Inn And Suites

Executive Inn And Suites
2.0 star property
Upper Marlboro
7.2 out of 10, Good, (605 reviews)
"Shops nearby Excellent staff Clean room Easy safe parking"
United States
Will
The price is ļæ„13,348
ļæ„15,082 total
includes taxes & fees
Jul 26 - Jul 27
Executive Inn And Suites
Lobby

20. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Nice hotel in downtown Annapolis walking distance to everything"
United States
Victoria
The price is ļæ„19,274
ļæ„21,971 total
includes taxes & fees
Jul 26 - Jul 27
Hilton Garden Inn Annapolis Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Shady Side attractions

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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Hotel has some age (couple hundred years) but thatā€™s to be expected of an historic landmark. Would definitely recommend and stay again!"
Gary 2-night trip
Posted 13 hours ago
Historic Inns of Annapolis

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
The price is ļæ„11,181 per night from Jul 26 to Jul 27
ļæ„11,181
ļæ„12,634 total
Jul 26 - Jul 27
includes taxes & fees

Frequently asked questions

Where is the best place for a stay in Shady Side?
Historic Inns of Annapolis, located 9.6 mi (15.4 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 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?
Cute, Cozy 2-bedroom house near Annapolis with water access: Visitors like this Shady Side vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. 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 Comfort Inn Largo-Washington DC East 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 75Ā°F, while the coldest months are January and February with an average of 40Ā°F. Average annual precipitation for Shady Side is 51 inches.

Explore a world of travel with Expedia