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! (45 reviews)
"This property was clean, comfortable, and offered all the little touches that made it feel like home. We loved the neighborhood and backyard and enjoyed walking and exploring the area. We hosted our Midshipman and a couple of her friends for her birthday and they loved relaxing at this house and ..."

Reviewed on Nov 5, 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 ¥13,253 per night from Nov 9 to Nov 10
¥13,253
¥15,132 total
Nov 9 - Nov 10
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 ¥11,226 per night from Nov 22 to Nov 23
¥11,226
¥18,184 total
Nov 22 - Nov 23
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! (45 reviews)
"This property was clean, comfortable, and offered all the little touches that made it feel like home. We loved the neighborhood and backyard and enjoyed walking and exploring the area. We hosted our Midshipman and a couple of her friends for her birthday and they loved relaxing at this house and ..."

Reviewed on Nov 5, 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 Oct 27, 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 Nov 1, 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