4 Stars Hotels in Shady Side, Maryland from CA $126

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Check prices for these dates

Tonight
Nov 11 - Nov 12
Tomorrow
Nov 12 - Nov 13
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Shady Side 4-star hotels

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

1. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,013 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is CA $184
CA $210 total
includes taxes & fees
Nov 29 - Nov 30
Graduate by Hilton Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

2. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,275 reviews)
"Excellent staff & service!"
United States
Michele
The price is CA $126
CA $144 total
includes taxes & fees
Nov 26 - Nov 27
DoubleTree by Hilton Hotel Annapolis
An outdoor patio area with wicker furniture, red umbrellas, and string lights.

3. DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC
4.0 star property
Upper Marlboro
8.2 out of 10, Very good, (1,000 reviews)
"Great stay and very nice staff breakfast was delicious and affordable"
United States
Shayna
The price is CA $131
CA $148 total
includes taxes & fees
Nov 24 - Nov 25
DoubleTree by Hilton Hotel Largo/Washington DC
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

4. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is CA $256
CA $320 total
includes taxes & fees
Dec 9 - Dec 10
The Inn at Chesapeake Bay Beach Club
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

5. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is CA $232
CA $264 total
includes taxes & fees
Nov 15 - Nov 16
The Westin Annapolis
The entrance to Rod N' Reel Resort with a covered walkway, a decorative fountain, and a stone wall with plants.

6. Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.8 out of 10, Excellent, (1,001 reviews)
"Place is gorgeous, clean and very welcoming."
United States
Patricia
The price is CA $195
CA $264 total
includes taxes & fees
Dec 1 - Dec 2
Rod 'N' Reel Resort
A balcony with a table set for two, overlooking a marina with boats.

7. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is CA $305
CA $348 total
includes taxes & fees
Nov 23 - Nov 24
Annapolis Waterfront Hotel, Autograph Collection
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

8. The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (46 reviews)
"Absolutely perfect little 3 day get away. The entire atmosphere was excellent, great complementary breakfast from menu, beautiful modern rooms, perfectly manicured landscaping with lots of seating for relaxing by the water. The entire staff were so friendly and helpful. We made an excellent choice and would definitely go back. 10+ out of 10."
United States
William
The price is CA $621
CA $684 total
includes taxes & fees
Nov 12 - Nov 13
The Oaks Waterfront
A modern kitchen with white cabinets, a wooden dining table set for four, and a view of the outdoors through large windows.

9. Legacy Villa

Legacy Villa
4.0 star property
Upper Marlboro
Legacy Villa

Top Shady Side Hotel Reviews

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis

10/10 Excellent

Bon emplacement et aux standards des Doubletree
Canada
Jean
Reviewed October 25, 2026
DoubleTree by Hilton Hotel Annapolis

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 $126

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.

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.

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