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

Shady Side Hotels

  • 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
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Filter by

Star rating

Guest rating

Our top choices for Shady Side hotels

Lobby
Lobby
Bar (on property)
Exterior

1. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
€88
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Annapolis
Exterior
Pool
Exterior
Fitness facility

2. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Heather
€95
includes taxes & fees
13 Sept - 14 Sept
Crowne Plaza Annapolis by IHG
Breakfast area
Room
Lobby
Terrace/patio

3. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Sophia
€96
includes taxes & fees
22 Sept - 23 Sept
Sonesta ES Suites Annapolis
Reception
Bar (on property)
Lobby
Garden

4. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Fabiana
€95
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Hotel Annapolis
Breakfast meal
Pool
Room
Exterior

5. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
€105
includes taxes & fees
13 Sept - 14 Sept
SpringHill Suites by Marriott Annapolis
Lobby
Exterior
Pool
Breakfast area

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

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
€93
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Annapolis, MD
Property amenity
Exterior
Property amenity
Pool

7. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
€94
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Annapolis
Dining
Lobby
Room
Fitness facility

8. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
€78
includes taxes & fees
13 Sept - 14 Sept
Best Western Annapolis
Front of property
Bar (on property)
View from property
View from room

9. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Dale
€195
includes taxes & fees
8 Sept - 9 Sept
Anchored Inn at Hidden Harbour Marina
Lobby
Room
Fitness facility
Lobby sitting area

10. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Javier
€96
includes taxes & fees
27 Sept - 28 Sept
Candlewood Suites Annapolis by IHG
Room, 1 King Bed, Non Smoking (Whirlpool)
Exterior
Exterior
Fitness facility

11. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
United States
Frank
€96
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Express & Suites Annapolis by IHG
Exterior
Breakfast area
Room
Reception

12. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Meghalee
€96
includes taxes & fees
21 Sept - 22 Sept
Hampton Inn & Suites Annapolis
Terrace/patio
Lounge
Lobby
Restaurant

13. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Gary
€115
includes taxes & fees
1 Sept - 2 Sept
Fairfield Inn & Suites By Marriott Annapolis
Lobby
Bar (on property)
Restaurant
Living area

14. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
Nelson
€103
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Annapolis Downtown
Meeting facility
Boating
Exterior
Boating

15. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
€134
includes taxes & fees
27 Sept - 28 Sept
Historic Inns of Annapolis
Terrace/patio
Lobby
Lobby
Lobby

16. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
Annapolis
United States
Caitlin
€132
includes taxes & fees
2 Sept - 3 Sept
Residence Inn By Marriott Annapolis
Dining
BBQ/picnic Area
Dining
Exterior

17. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Rachel
€115
includes taxes & fees
30 Aug - 31 Aug
Comfort Inn Conference Center
BBQ/picnic Area
Exterior
Room
Reception

18. TownePlace Suites by Marriott Annapolis

TownePlace Suites by Marriott Annapolis
Annapolis
United States
Jamila
€108
includes taxes & fees
7 Sept - 8 Sept
TownePlace Suites by Marriott Annapolis
Lobby
View from property
Bar (on property)
Property amenity

19. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
susan greco
€165
includes taxes & fees
30 Aug - 31 Aug
The Westin Annapolis
Front of property
Reception
Standard Double Room, 2 Double Beds
Outdoor pool

20. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Karen
€84
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn
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 savour its top-notch restaurants.
See properties

Captain Avery Museum

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

Learn more about Shady Side

Love dining, 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

St Michaels Inn

St Michaels Inn

8/10 Good
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"
CYNTHIA 3-night trip
Posted less than an hour ago
St Michaels Inn
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"for the rooms to be outdated they were well maintained & cleaned!! Staff was friendly breakfast was flavorful and parking was limited but available no issues"
Tarina 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Largo/Washington DC
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"."
ROBERT 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"The pool was soothing."
Oyedeji 1-night trip
Posted 1 hour ago
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Large room"
Michael William 3-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"It look like they did a lot of upgrades very nice. I really appreciate the staff and service. I will be back soon 😉"
Frankie 1-night trip
Posted 10 hours ago
Rod 'N' Reel Resort
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."
JOANA JENNIFER 2-night trip
Posted 11 hours ago
Hilton Garden Inn Annapolis Downtown
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"
Sophia 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Walking distance from the historic main street."
Daniel 1-night trip
Posted 3 days ago
The Westin 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
€77
30 Aug - 31 Aug
includes taxes & fees
WoodSpring Suites Washington DC East Arena Drive
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
€84
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,011 reviews)
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
€96
27 Sept - 28 Sept
includes taxes & fees
8.4/10 Very good! (1,001 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
€96
21 Sept - 22 Sept
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Hampton Inn & Suites Annapolis
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
€98
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,130 reviews)
Microtel Inn & Suites by Wyndham Gambrills
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
€115
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Comfort Inn Conference Center

Frequently asked questions

What's the best place to 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 traveller data. Two other choices for your visit 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 holiday rentals that Shady Side has to offer?
Steps to Chesapeake Bay! 'Callaway Drive Retreat': This highly rated holiday home rental in Shady Side is equipped with a patio, laundry facilities and cable TV to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Shady Side is Lovely bay views with kayaks, bikes, fire pit, crabbing & more. 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 room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Shady Side.
What are some accommodation options 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 on-site 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 accommodation options 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 itinerary are Captain Avery Museum and Franklin Point State Park. Take a look at what more there is 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 temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for Shady Side is 1307 mm.

Explore a world of travel with Expedia