Shady Side, MD

Travel Guide

A river with boats, a marina, and a town with houses and buildings.
An aerial view of a beach with clear water, a sandy shore, and visible footprints.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NT$2,903 per night from Jul 20 to Jul 21
NT$2,903
NT$4,411 total
Jul 20 - Jul 21
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,903 reviews)
"Great staff"

Reviewed on 2026/7/13

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
The price is NT$3,691 per night from Jul 28 to Jul 29
NT$3,691
NT$4,207 total
Jul 28 - Jul 29
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,039 reviews)
"Loved having a shuttle driver and having a full service restaurant on site."

Reviewed on 2026/7/13

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is NT$3,817 per night from Aug 2 to Aug 3
NT$3,817
NT$4,351 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,022 reviews)
"This hotel is in a convenient place, with several restaurants within walking distance and a mall just across the street. The front desk staff was helpful and polite. The hotel was not very clean. The carpets in the lobby and common areas appear dirty and stained. In the pool area, no clean towels ..."

Reviewed on 2026/7/13

Crowne Plaza Annapolis by IHG
See all 1,196 properties in Shady Side
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.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
1211 Baltimore Avenue Ocean City MD
Stay at this apartment in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are ...
7.8/10 Good! (40 reviews)
"Greatly enjoyed!!! Will stay again!!!"

Reviewed on 2026/7/11

Ocean Terrace Family Apartments
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

3 out of 5
200 59th Street on the Bay Ocean City MD
Stay at this aparthotel in Ocean City. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.4/10 Good! (1,310 reviews)
"Exceeded our expectations"

Reviewed on 2026/6/24

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
Shore Point Cottages

Shore Point Cottages

3 out of 5
9543 Stephen Decatur Hwy Berlin MD
Stay at this cottage in Berlin. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ocean ...
9.4/10 Exceptional! (341 reviews)
"Near the beach and pet friendly!!"

Reviewed on 2026/7/9

Shore Point Cottages
See all 14,639 properties in Maryland
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.

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