Shady Side 4 Stars Hotels

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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 NT$4,279
NT$4,879 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 NT$2,934
NT$3,344 total
includes taxes & fees
Nov 23 - Nov 24
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 NT$3,040
NT$3,436 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 NT$5,942
NT$7,431 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 NT$5,383
NT$6,137 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 NT$4,759
NT$6,376 total
includes taxes & fees
Nov 30 - Dec 1
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 NT$7,064
NT$8,052 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 NT$14,445
NT$15,890 total
includes taxes & fees
Nov 17 - Nov 18
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

Excellent and friendly service provided to hotel guests. From the front desk to restaurant, to housekeeping and also the Transport shuttle!
United States
Celina
Reviewed May 27, 2025
DoubleTree by Hilton Hotel Annapolis

Frequently Asked Questions

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

With Expedia's handy filter tool, scoring a superb deal on a 4-star hotel in Shady Side just got simpler. Start by keying in your chosen travel dates and length of your vacation. Then list the results by price and choose a hotel that best suits your budget and style.

  • Search for the lowest price from NT$2,933

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

Give yourself the luxury treatment during your Shady Side escape by staying at a 4-star hotel. As well as featuring upscale surroundings, these properties are typically filled with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your stay an even more lavish and special one. Concierge assistance, luxurious spas and gourmet dining are only the start of the exclusive services and conveniences you'll likely get access to.

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

Finding your dream vacation in Shady Side is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, food and activities, or opt for a standard 4-star resort in or around this leading destination.

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

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

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