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

Shady Side hotels from HK$628

  • 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
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Filter by

Star rating

Guest rating

Our top choices for Shady Side hotels

Front of property
View from room
Bar (on property)
View from property

1. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
United States
Dale
HK$1,562
HK$1,780 total
includes taxes & fees
9 Sept - 10 Sept
Anchored Inn at Hidden Harbour Marina
Breakfast meal
Reception
Room
Pool

2. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
HK$972
HK$1,108 total
includes taxes & fees
2 Sept - 3 Sept
SpringHill Suites by Marriott Annapolis
Reception
Lobby
Garden
Lobby

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Chereis
HK$705
HK$803 total
includes taxes & fees
7 Sept - 8 Sept
DoubleTree by Hilton Hotel Annapolis
Dining
Lobby
Dining
Exterior

4. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
United States
Rachel
HK$933
HK$1,054 total
includes taxes & fees
13 Sept - 14 Sept
Comfort Inn Conference Center
Lobby
Room
Breakfast area
Pool

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

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
HK$746
HK$851 total
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Annapolis, MD
Property amenity
Bar (on property)
Pool
Property amenity

6. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
HK$784
HK$894 total
includes taxes & fees
27 Sept - 28 Sept
Courtyard by Marriott Annapolis
Pool
Exterior
Fitness facility
Exterior

7. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Heather
HK$807
HK$920 total
includes taxes & fees
30 Sept - 1 Oct
Crowne Plaza Annapolis by IHG
Exterior
Lobby
Lobby
Food and drink

8. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
Gambrills
United States
William
HK$766
HK$874 total
includes taxes & fees
13 Sept - 14 Sept
Microtel Inn & Suites by Wyndham Gambrills
Room
Exterior
Exterior
Fitness facility

9. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
United States
Harold
HK$792
HK$903 total
includes taxes & fees
9 Sept - 10 Sept
Holiday Inn Express & Suites Annapolis by IHG
Breakfast area
Terrace/patio
Fitness facility
Lobby

10. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Sophia
HK$713
HK$813 total
includes taxes & fees
23 Sept - 24 Sept
Sonesta ES Suites Annapolis
Dining
Exterior
Fitness facility
Room

11. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
HK$628
HK$716 total
includes taxes & fees
27 Sept - 28 Sept
Best Western Annapolis
Property amenity
Reception
Exterior
Room

12. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
United States
Yolanda
HK$1,122
HK$1,268 total
includes taxes & fees
21 Sept - 22 Sept
Courtyard by Marriott Bowie
Meeting facility
Boating
Exterior
Boating

13. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Amy
HK$830
HK$1,214 total
includes taxes & fees
27 Sept - 28 Sept
Historic Inns of Annapolis
Lobby
Lobby
Property amenity
View from property

14. The Westin Annapolis

The Westin Annapolis
Annapolis
United States
susan greco
HK$1,403
HK$1,600 total
includes taxes & fees
13 Sept - 14 Sept
The Westin Annapolis
Terrace/patio
Breakfast meal
Lobby
Lobby

15. Residence Inn By Marriott Annapolis

Residence Inn By Marriott Annapolis
Annapolis
United States
Caitlin
HK$1,246
HK$1,421 total
includes taxes & fees
2 Sept - 3 Sept
Residence Inn By Marriott Annapolis
Exterior
Living area
Room
Room

16. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
United States
Meghalee
HK$765
HK$872 total
includes taxes & fees
9 Sept - 10 Sept
Hampton Inn & Suites Annapolis
Outdoor wedding area
Coffee shop
Sports bar
Interior

17. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Theresa
HK$1,133
HK$1,519 total
includes taxes & fees
1 Oct - 2 Oct
Rod 'N' Reel Resort
Lobby
Bar (on property)
Exterior
Lobby

18. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
HK$706
HK$805 total
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Annapolis
Terrace/patio
Restaurant
Lobby
Restaurant

19. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
Annapolis
United States
Gary
HK$1,129
HK$1,287 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites By Marriott Annapolis
Lobby
Bar (on property)
Living area
Room

20. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
JOANA JENNIFER
HK$893
HK$1,019 total
includes taxes & fees
9 Sept - 10 Sept
Hilton Garden Inn Annapolis Downtown
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

Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent
"Nice location, only about 4 miles to downtown Annapolis, an easy bike ride. Breakfast was more than adequate and the hotel and surrounding grounds clean. Lots of shopping nearby and a Whole Foods around the corner that is easily walked to."
George 2-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Clean room, great location."
Jeffrey 1-night trip
Posted 3 hours ago
Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Very good"
Adam 2-night trip
Posted 13 hours ago
Country Inn & Suites by Radisson, Annapolis, MD
St Michaels Inn

St Michaels Inn

10/10 Excellent
"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."
Alan 2-night trip
Posted 15 hours ago
St Michaels Inn
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"Clean room, easy check-in, nice amenities, though very limited staff for restaurant for a Saturday evening. The bartender, Willie, was great and helpful, though we opted to head next door to The Lodge for dinner."
Bryan 2-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"This is my go to hotel when I visit family. Ample parking, friendly staff, amenities, and they fresh bake cookies everyday and provide them to guests."
LaShanna 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Largo/Washington DC
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 9 days ago
Courtyard by Marriott Annapolis
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 weeks 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
HK$619
HK$700 total
2 Sept - 3 Sept
includes taxes & fees
WoodSpring Suites Washington DC East Arena Drive
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
HK$741
HK$815 total
2 Sept - 3 Sept
includes taxes & fees
8/10 Very good! (1,000 reviews)
St Michaels Inn
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
HK$765
HK$872 total
9 Sept - 10 Sept
includes taxes & fees
Hampton Inn & Suites Annapolis
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
HK$766
HK$874 total
13 Sept - 14 Sept
includes taxes & fees
9.2/10 Wonderful! (1,134 reviews)
Microtel Inn & Suites by Wyndham Gambrills
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
HK$792
HK$903 total
9 Sept - 10 Sept
includes taxes & fees
8.4/10 Very good! (1,006 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

4500 Crain Hwy Bowie MD
HK$933
HK$1,054 total
13 Sept - 14 Sept
includes taxes & fees
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?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: This highly rated holiday home rental in Shady Side offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. 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. You can relax into your holiday with a garden and a selection of games. Another good choice for your trip to Shady Side is Steps to Chesapeake Bay! 'Callaway Drive Retreat'. 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