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

Shady Side hotels from HK$676

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Check prices for these dates

Tonight
8 Sept - 9 Sept
Tomorrow
9 Sept - 10 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

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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$1,781 total
includes taxes & fees
10 Sept - 11 Sept
Anchored Inn at Hidden Harbour Marina
Breakfast meal
Room
Pool
Reception

2. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
HK$988
HK$1,126 total
includes taxes & fees
9 Sept - 10 Sept
SpringHill Suites by Marriott Annapolis
Reception
Bar (on property)
Garden
Lobby

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Chereis
HK$650
HK$741 total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Hotel Annapolis
Dining
BBQ/picnic Area
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
Pool
Breakfast area

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
4 Oct - 5 Oct
Country Inn & Suites by Radisson, Annapolis, MD
Property amenity
Exterior
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
Bar (on property)
Restaurant
Property amenity

7. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Cynthia
HK$862
HK$983 total
includes taxes & fees
27 Sept - 28 Sept
Crowne Plaza Annapolis by IHG
Exterior
Lobby
Lobby
Room

8. Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
Gambrills
United States
Mark
HK$813
HK$927 total
includes taxes & fees
20 Sept - 21 Sept
Microtel Inn & Suites by Wyndham Gambrills
Breakfast area
Fitness facility
Terrace/patio
Room

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
United States
Philip
HK$737
HK$840 total
includes taxes & fees
27 Sept - 28 Sept
Sonesta ES Suites Annapolis
Room
Breakfast meal
Room amenity
Room amenity

10. 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
27 Sept - 28 Sept
Holiday Inn Express & Suites Annapolis by IHG
Meeting facility
Boating
Meeting facility
Exterior

11. 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
View from property
Bar (on property)
Lobby

12. 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
Lobby
Living area
Room
Restaurant

13. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
Annapolis
United States
Jeffrey
HK$958
HK$1,092 total
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Annapolis Downtown
Property amenity
Room
Exterior
Reception

14. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
United States
Yolanda
HK$1,087
HK$1,228 total
includes taxes & fees
5 Oct - 6 Oct
Courtyard by Marriott Bowie
Outdoor wedding area
Sports bar
Interior
Hair salon

15. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
United States
Theresa
HK$1,133
HK$1,519 total
includes taxes & fees
4 Oct - 5 Oct
Rod 'N' Reel Resort
Dining
Exterior
Fitness facility
Room

16. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
HK$593
HK$676 total
includes taxes & fees
27 Sept - 28 Sept
Best Western Annapolis
Lobby
Lobby
Pool
Lobby

17. Hampton Inn & Suites Glenarden/Washington DC

Hampton Inn & Suites Glenarden/Washington DC
Lanham
United States
Jeffrey
HK$830
HK$937 total
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn & Suites Glenarden/Washington DC
Lobby
Exterior
Bar (on property)
Breakfast area

18. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
United States
Glenn
HK$708
HK$807 total
includes taxes & fees
16 Sept - 17 Sept
Hilton Garden Inn Annapolis
Property amenity
Lobby
Pool
Property amenity

19. Staybridge Suites Washington DC East - Largo by IHG

Staybridge Suites Washington DC East - Largo by IHG
Upper Marlboro
United States
Amy
HK$1,058
HK$1,196 total
includes taxes & fees
13 Sept - 14 Sept
Staybridge Suites Washington DC East - Largo by IHG
View from property
Lobby
Bar (on property)
Lobby

20. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
United States
Patricia
HK$1,215
HK$1,385 total
includes taxes & fees
1 Oct - 2 Oct
Graduate by Hilton Annapolis
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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 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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"The best thing about this hotel is the location. Right behind it is the historic charm. It’s one of the best in the country. The staff was very helpful. The room was spacious. The room was clean. The only thing it needed was newer television monitors. We were trying to watch the U.S. Open tennis and it was hard to follow the ball. Overall, excellent."
Pete 3-night trip
Posted 9 hours ago
Historic Inns of Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The lawn around the tennis court and pool need cutting/landscaping. Other than that the room was great and felt like a safe location."
Tanya 4-night trip
Posted 9 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Nice place. Breakfast was great pool needs more chairs."
Patricia 1-night trip
Posted 10 hours ago
St Michaels Inn
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Everything was fine but there’re not enough varieties for breakfast"
Selina 4-night trip
Posted 12 hours ago
Comfort Inn Largo-Washington DC East
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Helpful staff. We were in town for a USNA reunion, and the lobby café was surprisingly useful. Rendezvouses with classmates. Late evening bulk sessions. Decent coffee and snacks. Walking distance to stadium park n ride."
David 4-night trip
Posted 13 hours ago
Courtyard by Marriott Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Felt like we traveled to a southern town while still being in Maryland. Great hotel."
Michael 1-night trip
Posted 14 hours ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"GREAT location! The room was huge & beautifully decorated. We are excited to come back again! 10/10!"
Lori Ann 1-night trip
Posted 17 hours ago
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"Very clean room"
Morufat 2-night trip
Posted 18 hours ago
DoubleTree by Hilton Hotel Largo/Washington DC
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Great hotel! Wish the microwave was in the room."
Eric 1-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

More cheap stays in Shady Side

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
HK$593
HK$676 total
27 Sept - 28 Sept
includes taxes & fees
7.8/10 Good! (1,003 reviews)
Best Western Annapolis
WoodSpring Suites Washington DC East Arena Drive

WoodSpring Suites Washington DC East Arena Drive

1603 Brightseat Rd. Hyattsville MD
HK$619
HK$700 total
9 Sept - 10 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
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (1,000 reviews)
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
HK$792
HK$903 total
27 Sept - 28 Sept
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
Holiday Inn Express & Suites Annapolis by IHG
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD
HK$813
HK$927 total
20 Sept - 21 Sept
includes taxes & fees
Microtel Inn & Suites by Wyndham Gambrills
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 Crowne Plaza Annapolis by IHG and Graduate by Hilton Annapolis. 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. 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. Provides free self parking, an indoor pool and complimentary wireless Internet access. Rod 'N' Reel Resort and Sonesta ES Suites Annapolis 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.

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