Are there any 4-star casino hotels in Shady Side?

Shuffle between your room and the poker table with ease by using our filter tool to find 4-star casino hotels in and around Shady Side. Celebrating with somebody special? Narrow your search further by choosing amenities with that wow-factor, like a view or pool.

Find 4 Star Hotels in Shady Side, MD from $94

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Dates

February 2026

March 2026

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Our top choices for Shady Side 4-star hotels

DoubleTree by Hilton Hotel Largo/Washington DC

Upper Marlboro

Nadine

$98 nightly

Feb 28 - Mar 1

Total with taxes and fees

DoubleTree by Hilton Hotel Annapolis

Annapolis

Kathy

$83 nightly

Feb 22 - Feb 23

Total with taxes and fees

Graduate by Hilton Annapolis

Annapolis

Brian

$160 nightly

Feb 22 - Feb 23

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Micah

$203 nightly

Feb 22 - Feb 23

Total with taxes and fees

The Westin Annapolis

Annapolis

Robert

$179 nightly

Feb 15 - Feb 16

Total with taxes and fees

Rod 'N' Reel Resort

Chesapeake Beach

Thurnell

$128 nightly

Feb 26 - Feb 27

Total with taxes and fees

The Inn at Chesapeake Bay Beach Club

Stevensville

Alicia

$179 nightly

Feb 16 - Feb 17

Total with taxes and fees

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

Easton

Seth

$459 nightly

Feb 15 - Feb 16

Total with taxes and fees

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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shady Side.

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$513 nightly

$564 total

Feb 18 - Feb 19

Total with taxes and fees

9.4/10 Exceptional! (374 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Top Shady Side Hotel Reviews

The Westin Annapolis

10/10 Excellent

"The staff was wonderful, Room was spotless. Bar prices were insane for the area."

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent

"Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important. "

Find out more about Shady Side

Shady Side Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Shady Side, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Shady Side 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Shady Side. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Shady Side, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Shady Side hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Shady Side?

Expedia can help you quickly track down the perfect 4-star hotel for your vacation in Shady Side. Use our filter tool to fine-tune your search by things like budget, amenities and hotel star rating and get access to unbeatable deals in a few clicks.

Search for the lowest price from $405

What's the difference between 5-star and 4-star hotels in Shady Side?

If you choose to stay at a 4-star hotel in Shady Side, you'll typically find lots of conveniences to ensure you're relaxed, such as a restaurant, pool and gym. You can experience top-quality service and deluxe accommodations. Opt for a 5-star hotel and you'll get a few more perks — think on-site spas, 24-hour front desk and nightly turndown services. You're likely to get extra amenities and first-rate services at a 5-star getaway, but both are awesome options for luxury travelers.

Does Shady Side have any 4-star all-inclusive resorts?

Use our "All inclusive" filter to find your next getaway in Shady Side where everything is taken care of, from your meals to your room, entertainment and activities. We can also help you find standard 4-star stays in and around this leading destination.

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