Explore top 2026 4 Star Hotels in Shady Side

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Top Shady Side 4 Star hotels

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
$95 nightly
The price is $109 total per night from Jul 5 to Jul 6
$109 total
Jul 5 - Jul 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 business center and free WiFi in public areas. ...
8.6/10 Excellent! (1,008 reviews)
"Comfortable night sleep, and shuttle service to the academy while we were there."

Reviewed on Jun 27, 2026

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
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
$114 nightly
The price is $129 total per night from Jul 19 to Jul 20
$129 total
Jul 19 - Jul 20
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 5 conference rooms, along with the 24-hour business ...
Opens in a new windowDoubleTree by Hilton Hotel Largo/Washington DC
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
$212 nightly
The price is $241 total per night from Jul 5 to Jul 6
$241 total
Jul 5 - Jul 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 24-hour business center, free WiFi in public ...
8.8/10 Excellent! (939 reviews)
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. ..."

Reviewed on Jun 17, 2026

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Jul 5 to Jul 6
$193 total
Jul 5 - Jul 6
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 ...
8.8/10 Excellent! (1,002 reviews)
"Ed frames broken, heavenly bed experience was compromised. This was the worst Westin hotel I have ever experienced"

Reviewed on Jun 16, 2026

Opens in a new windowThe Westin Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $179 total per night from Jul 5 to Jul 6
$179 total
Jul 5 - Jul 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, ...
9.4/10 Exceptional! (1,001 reviews)
"Convenient location. Beautiful property. Friendly staff!"

Reviewed on Jun 27, 2026

Opens in a new windowGraduate by Hilton Annapolis
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
$167 nightly
The price is $186 total per night from Jul 5 to Jul 6
$186 total
Jul 5 - Jul 6
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 ...
8.6/10 Excellent! (1,002 reviews)
"The stay was great! We had issues with booking through Expedia, but the manager (Ty) made sure to correct the issue!"

Reviewed on Jun 25, 2026

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
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $276 total per night from Jun 29 to Jun 30
$276 total
Jun 29 - Jun 30
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this traditional hotel. Enjoy the seasonal outdoor pool and perks like free self parking ...
9.4/10 Exceptional! (467 reviews)
"The restaurant was wonderful and so was the staff. The grounds were gorgeous and interesting."

Reviewed on Jun 24, 2026

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 Easton MD
Fully refundableReserve now, pay when you stay
$489 nightly
The price is $538 total per night from Jun 29 to Jun 30
$538 total
Jun 29 - Jun 30
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 ...
Opens in a new windowThe Oaks Waterfront
Legacy Villa

Legacy Villa

4 out of 5
12605 Brooke Lane Upper Marlboro MD
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

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