A river with boats, a marina, and a town with houses and buildings.

Shady Side Hotel Guide - 4 Stars Hotels in Shady Side, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side 4 Star Hotels

Our top choices for Shady Side 4-star hotels

A spacious atrium with a high ceiling, skylights, and a patterned floor.

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 Rp2.357.922
Rp2.688.031 total
includes taxes & fees
29 Nov - 30 Nov
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, (1,274 reviews)
"Excellent staff & service!"
United States
Michele
The price is Rp1.614.382
Rp1.840.395 total
includes taxes & fees
25 Nov - 26 Nov
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, (1,002 reviews)
"Great stay and very nice staff breakfast was delicious and affordable"
United States
Shayna
The price is Rp1.826.971
Rp2.064.477 total
includes taxes & fees
30 Nov - 1 Dec
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 Rp3.269.732
Rp4.088.899 total
includes taxes & fees
9 Dec - 10 Dec
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 Rp2.962.168
Rp3.376.871 total
includes taxes & fees
15 Nov - 16 Nov
The Westin Annapolis
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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 Rp2.622.145
Rp3.512.811 total
includes taxes & fees
30 Nov - 1 Dec
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, (1,001 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is Rp3.891.892
Rp4.436.756 total
includes taxes & fees
23 Nov - 24 Nov
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 Rp7.949.086
Rp8.743.995 total
includes taxes & fees
15 Nov - 16 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Rp7.864.543 per night from 9 Dec to 10 Dec
Rp7.864.543
Rp8.650.998 total
9 Dec - 10 Dec
includes taxes & fees
9.6/10 Exceptional! (407 reviews)
Still don't see what you're looking for?
See all properties in Shady Side.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

Love dining, parks and museums? Get away to Shady Side!

See all hotels in Shady Side
A river with boats, a marina, and a town with houses and buildings.

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great place……………………………….."
Scott 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Shady Side?
We can help you easily locate the ideal 4-star hotel for your trip to Shady Side. Use our handy filter tool to tailor your search by things like price, amenities and property star rating and get access to fabulous deals in a few clicks.

  • Search for the lowest price from Rp7.203.237

What's the difference between 5-star and 4-star hotels in Shady Side?
Treat yourself to refined living during your Shady Side holiday by staying at a 4-star hotel. As well as featuring upscale surroundings, these properties are typically filled with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go the extra mile to make your trip an even more indulgent and special one. Concierge assistance, luxurious spas and world-class dining are a few of the exclusive services and conveniences you'll likely be able to enjoy.
Does Shady Side have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your dream resort in Shady Side where everything is taken care of, from your accommodation to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this destination.