Shady Side Hotels from S$118

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Shady Side hotels

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (867)
"Great place"
The price is S$168
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (955)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is S$215
includes taxes & fees
20 Jul - 21 Jul
Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (574)
"Great place to stay. "
The price is S$281
includes taxes & fees
8 Jul - 9 Jul
Hyatt Place Kent Narrows & Marina

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"Easy downtown location, walkable to waterfront and great restaurants "
The price is S$233
includes taxes & fees
13 Jul - 14 Jul
The Westin Annapolis

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1005)
"Pleasant stay!!"
The price is S$145
includes taxes & fees
24 Jul - 25 Jul
Courtyard by Marriott Annapolis

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1003)
"I liked the spacious room and Jacuzzi. The free breakfast was good and staff was Amazing!"
The price is S$127
includes taxes & fees
13 Jul - 14 Jul
Hilton Garden Inn Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1002)
"Clean and comfortable room a with friendly service. Also in a great location to access the surrounding area. "
The price is S$133
includes taxes & fees
24 Jul - 25 Jul
Hampton Inn & Suites Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (835)
"Front desk staff was very friendly and helpful."
The price is S$312
includes taxes & fees
4 Aug - 5 Aug
Annapolis Waterfront Hotel, Autograph Collection

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Great location , perfect for my family stay."
The price is S$147
includes taxes & fees
13 Jul - 14 Jul
Country Inn & Suites by Radisson, Annapolis, MD

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1009)
"Nice hotel"
The price is S$144
includes taxes & fees
3 Aug - 4 Aug
DoubleTree by Hilton Hotel Annapolis

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Decent property "
The price is S$166
includes taxes & fees
9 Jul - 10 Jul
Holiday Inn Express & Suites Annapolis by IHG

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1792)
"Wonderful stay!"
Historic Inns of Annapolis

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (399)
"Staff was very polite and friendly. "
The price is S$336
includes taxes & fees
22 Jul - 23 Jul
The Inn at Chesapeake Bay Beach Club

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1003)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is S$157
includes taxes & fees
15 Jul - 16 Jul
Crowne Plaza Annapolis by IHG

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (104)
"Wonderful stay. "
The price is S$184
includes taxes & fees
13 Jul - 14 Jul
Fairfield Inn & Suites By Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Great location , clean and friendly staff "
The price is S$147
includes taxes & fees
13 Jul - 14 Jul
SpringHill Suites by Marriott Annapolis

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (48)
"Excellent stay. Very relaxing and great facilities."
The price is S$303
includes taxes & fees
8 Jul - 9 Jul
Wylder Tilghman Island

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (834)
"Room was large & bed very comfortable. Very pleasant stay"
The price is S$150
includes taxes & fees
20 Jul - 21 Jul
Sonesta ES Suites Annapolis

Village Inn

2.0 star property
6.2 out of 10, (486)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is S$120
includes taxes & fees
8 Jul - 9 Jul
Village Inn

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1004)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is S$179
includes taxes & fees
24 Jul - 25 Jul
Best Western Kent Narrows Inn
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Shady Side

Love dining, parks and museums? Get away to Shady Side!

Frequently asked questions

What's the best place to 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 traveller data. Two other choices for your visit to the area are La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway and Comfort Inn Largo-Washington DC East. 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 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?

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool and buffet. Comfort Inn Largo-Washington DC East 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 12 hotels and other accommodation options to choose from. Find out more about Shady Side.

What should I see while I'm in Shady Side?

Favourite places to visit include Shadyside Park, Captain Avery Museum and Franklin Point State Park. You'll also find London Town and Maryland Quiet Waters Park in the area. 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.