Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Check availability on Shady Side 4 Star Hotels

Our top choices for Shady Side 4-star hotels

Exterior

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, (1,010 reviews)
"Great Stay"
United States
Richard
The price is 3.000.068 ₫
3.390.077 ₫ total
includes taxes & fees
7 Jul - 8 Jul
DoubleTree by Hilton Hotel Largo/Washington DC
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,016 reviews)
"It was one of the nicest places we've stayed in our travels."
United States
William
The price is 2.927.229 ₫
3.337.042 ₫ total
includes taxes & fees
15 Jun - 16 Jun
DoubleTree by Hilton Hotel Annapolis
View from property

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,007 reviews)
"Very fine place"
United States
David
The price is 4.819.398 ₫
5.494.114 ₫ total
includes taxes & fees
12 Jul - 13 Jul
Graduate by Hilton Annapolis
Lobby lounge

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"Good location, nice hotel"
United States
Jiyoung
The price is 4.974.669 ₫
5.671.123 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Westin Annapolis
Premium bedding, down duvets, pillow-top beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (937 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is 6.465.754 ₫
7.370.960 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Annapolis Waterfront Hotel, Autograph Collection
Outdoor wedding area

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,003 reviews)
"Awesome spot and room, nice walking distance from multiple places"
United States
Travis
The price is 3.803.253 ₫
5.011.240 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Rod 'N' Reel Resort
Front of property – evening/night

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, (457 reviews)
"The entire place was beautiful, the staff, room, shops, restaurants all were amazing. Thanks"
United States
Winfred
The price is 5.938.265 ₫
7.261.081 ₫ total
includes taxes & fees
16 Jun - 17 Jun
The Inn at Chesapeake Bay Beach Club
Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is 11.583.872 ₫
12.742.259 ₫ total
includes taxes & fees
21 Jun - 22 Jun
The Oaks Waterfront
Family House | In-room dining

Legacy Villa

Legacy Villa
4.0 star property
Upper Marlboro
Legacy Villa
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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
The price is 17.529.786 ₫ per night from 1 Jul to 2 Jul
17.529.786 ₫
19.282.765 ₫ total
1 Jul - 2 Jul
includes taxes & fees
9.6/10 Exceptional! (390 reviews)
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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.

Learn more about Shady Side

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Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

Top Shady Side Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

6/10 Okay
"One elevator didn’t work and the other elevator was unreliable. The restaurant is closed. The hallway and rooms feel more like a 1970’s Best Western - well worn and not without a musty odor. The HVAC in room 518 is either off or cooling the room to 65 degrees (nothing in the middle). It’s an older property and ,other than scraping it, I don’t know how you could correct all of the issues."
John 2-night trip
Posted 7 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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 holiday. Then list the results by price and choose a hotel that best suits your budget and style.

  • Search for the lowest price from 9.906.911 ₫

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 holiday 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 accommodation, food and activities, or opt for a standard 4-star resort in or around this leading destination.