Explore top 2026 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
$121 nightly
The price is $137 total per night from May 17 to May 18
$137 total
May 17 - May 18
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. ...
8.2/10 Very Good! (1,002 reviews)
Breakfast was mediocre, only 1 elevator worked. Staff was amazing!!!

Reviewed on May 13, 2026

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
$114 nightly
The price is $130 total per night from May 31 to Jun 1
$130 total
May 31 - Jun 1
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! (1,002 reviews)
The room was clean. The bed was comfortable. The staff was friendly and helpful.

Reviewed on May 13, 2026

Opens in a new windowDoubleTree by Hilton Hotel 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
$212 nightly
The price is $241 total per night from May 25 to May 26
$241 total
May 25 - May 26
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! (927 reviews)
After a long day of travel, we decided the same day to book a stay in Annapolis as a middle point in our road trip. The hotel was so beautiful from the outside and just as lovely inside. I complimented both of the main desk staff members at check in and check out, it was notable how friendly and ...

Reviewed on May 6, 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 Jun 7 to Jun 8
$193 total
Jun 7 - Jun 8
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! (1,000 reviews)
Certain staff seemed to be under the impression that they were much better than the patrons, and couldn’t take the time to give great support. Some were exemplary

Reviewed on May 11, 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
$163 nightly
The price is $186 total per night from Jun 7 to Jun 8
$186 total
Jun 7 - Jun 8
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! (1,008 reviews)
GREAT LOCATION VERY CLEAN FACILITY

Reviewed on May 12, 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
$162 nightly
The price is $177 total per night from May 25 to May 26
$177 total
May 25 - May 26
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! (1,003 reviews)
Nice location

Reviewed on May 12, 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 May 25 to May 26
$276 total
May 25 - May 26
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! (454 reviews)
We did eat breakfast but the day of check in we enjoyed lunch, very good! We stayed in The Barn, the room was very clean and beautiful. Our only problem we found was the mattress was way too soft. My husband and I both agree they need a new mattress. Everything else was excellent ‼️

Reviewed on May 3, 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 May 17 to May 18
$538 total
May 17 - May 18
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 ...
10/10 Exceptional! (41 reviews)
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.

Reviewed on Nov 28, 2025

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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