Shady Side
Travel Guide
Visit Shady Side
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (40 reviews)
"We really enjoyed our stay. The location is great. The backyard is great for dogs. The hostess is very responsive and wonderful to work with."
Reviewed on Sep 17, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is CA $138 per night from Oct 12 to Oct 13
CA $138
CA $157 total
Oct 12 - Oct 13
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 ...
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is CA $122 per night from Nov 1 to Nov 2
CA $122
CA $188 total
Nov 1 - Nov 2
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! (2,028 reviews)
"The staff was fantastic and our only issue was the toilet clogged a couple times but we would stay again Thanks"
Reviewed on Oct 4, 2026
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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (40 reviews)
"We really enjoyed our stay. The location is great. The backyard is great for dogs. The hostess is very responsive and wonderful to work with."
Reviewed on Sep 17, 2026
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."
Reviewed on Aug 3, 2026
Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River
Arnold MD
Stay at this cottage in Arnold. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Annapolis City Dock and Bay Hills Golf Club are located ...
10/10 Exceptional! (1 review)
"This property is a dream! Many amenities that are hard to find in other rentals. The kitchen is fully stocked with cooking items, which made eating in much easier. Our Mid had surgery and this provided the perfect space to relax away from the Yard. 20 minutes away from DTA with a view of the Magothy ..."
Reviewed on Sep 28, 2026
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.
