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

Shuffle between your room and the blackjack table with ease by using our filters to find 4-star casino hotels in and around Shady Side. Celebrating with someone special? Refine your search further by selecting amenities with that extra wow-factor, like a hot tub or view.

4 Stars Hotels in Shady Side, Maryland from CA $173

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Dates

April 2026

May 2026

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Our top choices for Shady Side 4-star hotels

Graduate by Hilton Annapolis

Annapolis

James

CA $320 total

includes taxes & fees

Apr 12 - Apr 13

DoubleTree by Hilton Hotel Largo/Washington DC

Upper Marlboro

Shawnna

CA $187 total

includes taxes & fees

Apr 19 - Apr 20

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

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Douglas

CA $459 total

includes taxes & fees

Apr 12 - Apr 13

DoubleTree by Hilton Hotel Annapolis

Annapolis

Emily

CA $173 total

includes taxes & fees

Apr 5 - Apr 6

Rod 'N' Reel Resort

Chesapeake Beach

David

CA $234 total

includes taxes & fees

Apr 20 - Apr 21

The Westin Annapolis

Annapolis

Brandi

CA $285 total

includes taxes & fees

Apr 5 - Apr 6

The Inn at Chesapeake Bay Beach Club

Stevensville

Byron

CA $323 total

includes taxes & fees

Apr 5 - Apr 6

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

The Oaks Waterfront

Easton

Jeffrey

CA $674 total

includes taxes & fees

Apr 6 - Apr 7

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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

CA $796

CA $875 total

Apr 19 - Apr 20

includes taxes & fees

9.6/10 Exceptional! (377 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

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great location, friendly staff and clean rooms"

Annapolis Waterfront Hotel, Autograph Collection

6/10 Okay

"All restaurants onsite were not open! We had to order from a restaurant nearby but it really was not set up properly for room service. We had to go there to order and pickup and they were not really sure of the process for hotel guests so we just paid with a separate CC. Breakfast was essentially not available and we had to go to town to pickup breakfast as well. The heat in our room did not work for the first day and night! The hotel knew they had a situation going on but did not say anything to us in advance and the hotel was sold-out.At first they suggested a space heater but then another supervisor came on duty and told us those were not premitted - and we could understand why. It was fixed by our second night. We were told we would get a credit toward the first night but we did not?"

Find out more about Shady Side

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Shady Side are calling your name. Known for providing first-rate service in amazing locations, each of the Shady Side 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Shady Side. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shady Side, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Shady Side hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

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

To find a 4-star hotel in Shady Side that matches your budget, use Expedia's filter tool. Check out the available options during your travel dates and use our pricing filter to set your limit. You can also sort your results by the most affordable stay first.

Search for the lowest price from CA $409

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

If you choose to book a stay at a 4-star hotel in Shady Side, you'll usually find loads of amenities to ensure you're relaxed, such as a restaurant, gym and pool. You can enjoy top-quality service and upmarket surroundings. Opt for a 5-star hotel and you'll get a few extra bells and whistles — think around-the-clock concierge, on-site spas and nightly turndown services. You're likely to get additional amenities and exclusive services at a 5-star stay, though both are fabulous options for luxury travellers.

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

Enjoy a relaxing vacation experience where just about everything is included in the one rate by using our "All inclusive" filter. Keeping to your budget is a breeze when your meals, accommodations and activities are already taken care of. Eager for more ideas? Browse the terrific deals on Expedia's standard 4-star resorts in and around Shady Side too.

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