A river with boats, a marina, and a town with houses and buildings.

Find Beach Hotels in Shady Side, MD

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Beach Hotels

Tonight
Sep 20 - Sep 21
Tomorrow
Sep 21 - Sep 22
Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4

Our top choices for Shady Side beach hotels

1. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Stroll to sandy shores from this serene Maryland escape, where a seasonal pool, relaxing hot tub, and complimentary bicycles await.
NT$12,622
NT$14,390 total
includes taxes & fees
Sep 27 - Sep 28
The Inn at Tacaro Estate

2. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
NT$3,105
NT$3,540 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn & Suites Annapolis

3. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
NT$3,193
NT$3,640 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard by Marriott Annapolis

4. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
NT$2,991
NT$3,567 total
includes taxes & fees
Sep 27 - Sep 28
Candlewood Suites Annapolis by IHG

5. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
NT$4,105
NT$4,680 total
includes taxes & fees
Sep 27 - Sep 28
SpringHill Suites by Marriott Annapolis

6. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
NT$3,214
NT$3,664 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express & Suites Annapolis by IHG
View all properties

Choose what matters most at beach hotels in Shady Side

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Find out more about Shady Side

Shady Side and its attractions for beach lovers

Shady Side, Maryland, offers a charming waterfront experience that beach lovers will truly relish. Start your adventure at the picturesque Chesapeake Bay, where you can indulge in swimming, kayaking, and paddleboarding amidst stunning sunsets. The nearby Jug Bay Wetlands Sanctuary provides an opportunity for nature walks and birdwatching, making it a perfect spot for families who enjoy outdoor activities. For a delightful afternoon, visit the local seafood shacks, where you can savor the freshest crab cakes and oysters right by the water. If you're seeking a bit of history, the Shady Side area is dotted with quaint fishing villages that tell the story of the Chesapeake's maritime heritage. Staying near the water, such as at a cozy boutique hotel or a charming inn, allows you to wake up to the sound of waves and enjoy easy access to both beaches and local attractions, ensuring a delightful blend of relaxation and adventure for you and your family.

Top Shady Side Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"very clean"
Jolyn 2-night trip
Posted 3 hours ago
Rod 'N' Reel Resort
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Convenient location. Clean room. I was just there to sleep while attending the Maryland Seafood Festival. Parking was fine. Breakfast was okay. I had just spent two days pigging out on Maryland seafood. Okay for breakfast is a compliment!"
Michael 2-night trip
Posted 10 hours ago
Best Western Annapolis

Frequently asked questions

What is Shady Side like for travelers who love the beach?
Discover your ideal place to stay in Shady Side, which has a lot to offer the traveler looking for a beach getaway.
When's the best time for a beach vacation in Shady Side?
You can plan your beach trip with this snapshot of weather throughout the year in Shady Side: The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Shady Side is 51 inches.
What is there to see and do around Shady Side?
After arriving and settling in at your accommodation of choice, you might want to venture out and explore. Beach lovers can head straight to Sandy Point Beach or Triton Beach for some quality time by the water. Discover a variety of local attractions, which include Northern Chesapeake Bay and Chesapeake Bay. For more things to see and do, consider visiting Shadyside Park or Captain Avery Museum.
What's the best way to get to my beach hotel in Shady Side?
This travel information can help you get to and around your beach accommodation in Shady Side more easily: The closest major airport is Fort Meade, MD (FME-Tipton), located 21.6 mi (34.8 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia