4 Stars Hotels in Shady Side, Maryland from CA $129

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Dates

February 2026

9

March 2026

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Check availability on Shady Side 4 Star Hotels

Tonight

Tomorrow

Feb 10 - Feb 11

This weekend

Feb 13 - Feb 15

Next weekend

Feb 20 - Feb 22

Our top choices for Shady Side 4-star hotels

Exterior

DoubleTree by Hilton Hotel Largo/Washington DC

Upper Marlboro

United States

Nadine

CA $151 total

includes taxes & fees

Feb 23 - Feb 24

Reception

DoubleTree by Hilton Hotel Annapolis

Annapolis

United States

Jose Miguel

CA $129 total

includes taxes & fees

Feb 22 - Feb 23

Lobby

Graduate by Hilton Annapolis

Annapolis

United States

Brian

CA $250 total

includes taxes & fees

Feb 15 - Feb 16

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

Annapolis Waterfront Hotel, Autograph Collection

Historic District

United States

Micah

CA $317 total

includes taxes & fees

Feb 15 - Feb 16

Property amenity

The Westin Annapolis

Annapolis

United States

Robert

CA $263 total

includes taxes & fees

Feb 15 - Feb 16

Outdoor wedding area

Rod 'N' Reel Resort

Chesapeake Beach

United States

Thurnell

CA $171 total

includes taxes & fees

Feb 17 - Feb 18

Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

Stevensville

United States

Alicia

CA $272 total

includes taxes & fees

Feb 11 - Feb 12

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

The Oaks Waterfront

Easton

United States

Seth

CA $621 total

includes taxes & fees

Feb 13 - Feb 14

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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

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

CA $702

CA $772 total

Feb 11 - Feb 12

includes taxes & 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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent

"Nice staff"

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Stayed here for two nights and had a wonderful experience. The staff was exceptional and truly went above and beyond to make sure everything was perfect. The room was clean, the hotel was quiet, and I felt very comfortable throughout my stay. I would absolutely recommend this hotel to friends and family."

DoubleTree by Hilton Hotel Largo/Washington DC

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

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 $772

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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