Find 4 Star Hotels in Shady Side, MD from SAR 349
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Shady Side 4 Star Hotels
Tonight
Tomorrow
This weekend
Next weekend
Compare Shady Side 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

DoubleTree by Hilton Hotel Largo/Washington DC
DoubleTree by Hilton Hotel Largo/Washington DC
8.0 out of 10, Very Good, (1002)
The price is SAR 443
SAR 501 total
includes taxes & fees
26 Mar - 27 Mar

DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
8.6 out of 10, Excellent, (1003)
The price is SAR 349
SAR 398 total
includes taxes & fees
17 Mar - 18 Mar

Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
9.4 out of 10, Exceptional, (1004)
The price is SAR 635
SAR 723 total
includes taxes & fees
16 Mar - 17 Mar

The Westin Annapolis
The Westin Annapolis
8.6 out of 10, Excellent, (1000)
The price is SAR 484
SAR 552 total
includes taxes & fees
13 Mar - 14 Mar

Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
8.8 out of 10, Excellent, (803)
The price is SAR 807
SAR 920 total
includes taxes & fees
23 Mar - 24 Mar

Rod 'N' Reel Resort
Rod 'N' Reel Resort
8.2 out of 10, Very Good, (1002)
The price is SAR 435
SAR 558 total
includes taxes & fees
26 Mar - 27 Mar

The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
9.4 out of 10, Exceptional, (375)
The price is SAR 656
SAR 824 total
includes taxes & fees
7 Apr - 8 Apr

The Oaks Waterfront
The Oaks Waterfront
10.0 out of 10, Exceptional, (29)
The price is SAR 1,448
SAR 1,593 total
includes taxes & fees
26 Mar - 27 Mar
Save an average of 15% on thousands of hotels when you're signed in
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
308 Watkins Ln, St. Michaels, MD
The price is SAR 1,448 per night from Apr 1 to Apr 2
SAR 1,448
SAR 1,752 total
includes taxes & fees
1 Apr - 2 Apr
9.4/10 Exceptional! (332 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.
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 out, parks, and museums? Get away to Shady Side!
Recent reviews of Shady Side hotels
Recent reviews of Shady Side hotels

Graduate by Hilton Annapolis
5/5 Excellent
Go to hotel in Annapolis
"Always a wonderful stay at the Graduate!! My go to hotel when staying in Annapolis. Did two nights; one with my daughter for a mother/daughter night out, and one for after the Saint patty’s day parade!
We had dinner at the trophy room Saturday night and it was good! Service was a little slow but they were fairly busy with what looked to be only two servers! Our waitress was very friendly either way and we had a good time!"
A verified traveler stayed at Graduate by Hilton Annapolis
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Shady Side Hotels by Star Rating
Stay near popular Shady Side attractions
- Hotels near Shadyside Park
- Hotels near Captain Avery Museum
- Hotels near U.S. Naval Academy
- Hotels near Northwest Stadium
- Hotels near Six Flags America
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near Anne Arundel Medical Center
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Show Place Arena
- Hotels near Annapolis Mall Shopping Center
- Hotels near Westfield Annapolis Mall
- Hotels near Bowie State University
- Hotels near Maryland Quiet Waters Park
- Hotels near St. Michaels Winery
- Hotels near Breezy Point Beach
- Hotels near Prince George's Community College
- Hotels near Annapolis Maritime Museum
- Hotels near Maryland State House
Explore more hotels
- The Westin Annapolis
- Crowne Plaza Annapolis by IHG
- Holiday Inn Express I-95 Capitol Beltway-Largo by IHG
- Staybridge Suites Washington DC East - Largo by IHG
- Staybridge Suites Washington D.C.- Greenbelt by IHG
- SpringHill Suites by Marriott Annapolis
- Hampton Inn & Suites Glenarden/Washington DC
- Hyatt Place Kent Narrows & Marina
- Comfort Inn Conference Center
- Courtyard by Marriott Annapolis
- Inn at Perry Cabin
- Residence Inn Largo Medical Center Drive
- Courtyard Largo Medical Center Drive
- Comfort Inn Largo-Washington DC East
- Sonesta ES Suites Annapolis
- WoodSpring Suites Washington DC East Arena Drive
- Holiday Inn Express & Suites Annapolis by IHG
- Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD
- Fairfield Inn & Suites By Marriott Annapolis
- Sleep Inn & Suites Near Joint Base Andrews - Washington Area