Explore top 2025 4 Star Hotels in Shady Side

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Top Shady Side 4 Star hotels

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $121 total per night from Sep 29 to Sep 30
$121 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and WiFi in public areas. ...
7.8/10 Good! (1,014 reviews)
"Great staff"

Reviewed on Sep 22, 2025

Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $121 total per night from Sep 29 to Sep 30
$121 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
8.6/10 Excellent! (1,015 reviews)
McMullen Symposium
"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."

Reviewed on Sep 21, 2025

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $227 total per night from Sep 28 to Sep 29
$227 total
Sep 28 - Sep 29
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business ...
8.6/10 Excellent! (1,005 reviews)
"Excellent hotel"

Reviewed on Sep 14, 2025

Opens in a new windowThe Westin Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
$180 nightly
The price is $205 total per night from Oct 5 to Oct 6
$205 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...
9.2/10 Wonderful! (1,010 reviews)
"What a great hotel. Navy themed. Great location."

Reviewed on Sep 17, 2025

Opens in a new windowGraduate by Hilton Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $290 total per night from Oct 19 to Oct 20
$290 total
Oct 19 - Oct 20
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
8.8/10 Excellent! (865 reviews)
"Y"

Reviewed on Sep 17, 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $185 total per night from Sep 29 to Sep 30
$185 total
Sep 29 - Sep 30
Total with taxes and fees
A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax ...
8.2/10 Very Good! (1,010 reviews)
"The hotel was not as comfortable as described, firstly the beds are double beds, difficult for two adults to sleep in, the beds were not comfortable and something on the of the bed was very sharp. Air conditioner was very noisy."

Reviewed on Sep 22, 2025

Opens in a new windowRod 'N' Reel Resort
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road, Stevensville, MD
$228 nightly
The price is $253 total per night from Oct 26 to Oct 27
$253 total
Oct 26 - Oct 27
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this traditional hotel. Traveling on business? Take advantage of the 24-hour business ...
9.4/10 Exceptional! (419 reviews)
"Peace and tranquility"

Reviewed on Sep 2, 2025

Opens in a new windowThe Inn at Chesapeake Bay Beach Club
The Oaks Waterfront

The Oaks Waterfront

4 out of 5
25876 Royal Oak Road, Royal Oak, Easton, MD
Fully refundableReserve now, pay when you stay
$459 nightly
The price is $505 total per night from Sep 28 to Sep 29
$505 total
Sep 28 - Sep 29
Total with taxes and fees
This bed & breakfast features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy the a rooftop terrace and free perks like cooked-to-order breakfast ...
9.8/10 Exceptional! (38 reviews)
Get away
"Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?"

Reviewed on Sep 2, 2025

Opens in a new windowThe Oaks Waterfront
Legacy Villa

Legacy Villa

4 out of 5
12605 Brooke Lane, Upper Marlboro, MD
$168 nightly
The price is $190 total per night from Oct 9 to Oct 10
$190 total
Oct 9 - Oct 10
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. WiFi in public areas is free. A garden, a picnic area, ...
Opens in a new windowLegacy Villa
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4 Star Hotels Shady Side

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Shady Side 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Shady Side will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Shady Side, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Shady Side hotel reviews by fellow wanderers