Explore top 2026 4 Star Hotels in Shady Side

Name: The Inn at Chesapeake Bay Beach Club
Price range: $276 total
Rating: 9.4

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Top Shady Side 4 Star hotels

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

Fully refundableReserve now, pay when you stay

$121 nightly

$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

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$114 nightly

$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

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$212 nightly

$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

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$169 nightly

$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

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$163 nightly

$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

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$162 nightly

$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

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$249 nightly

$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

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$489 nightly

$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

Legacy Villa

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, ...

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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.