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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

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! (44 reviews)
"Family members used this property for a home base so we could take day trips to Annapolis, DC and other small towns. Nice home with comfortable beds, nice linens and a fully stocked kitchen in a quiet neighborhood. The wood floors & fenced back yard were great for our dog, also appreciated the off-street ..."

Reviewed on 17 October 2026

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3 out of 5
55 Hampton Park Blvd Capitol Heights MD
The price is AED 309 per night from Nov 9 to Nov 10
AED 309
AED 353 total
9 Nov - 10 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is AED 315 per night from Dec 1 to Dec 2
AED 315
AED 484 total
1 Dec - 2 Dec
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 ...
Historic Inns of Annapolis
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

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! (44 reviews)
"Family members used this property for a home base so we could take day trips to Annapolis, DC and other small towns. Nice home with comfortable beds, nice linens and a fully stocked kitchen in a quiet neighborhood. The wood floors & fenced back yard were great for our dog, also appreciated the off-street ..."

Reviewed on 17 October 2026

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River

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! (5 reviews)
"Great location, excellent quality accommodations. Host communication was quick and helpful."

Reviewed on 27 October 2026

Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River
Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access

Crownsville MD
Stay at this vacation home in Crownsville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.8/10 Exceptional! (31 reviews)
"Very nice place, clean and updated! We enjoyed our time there"

Reviewed on 1 November 2026

Cute, Cozy 2-bedroom house near Annapolis with water access
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