Explore top 2026 4 Star Hotels in Shady Side

Name: The Inn at Chesapeake Bay Beach Club
Price range: $199 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

$98 nightly

$110 total

Feb 25 - Feb 26

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! (1,007 reviews)

Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important.

Reviewed on Feb 1, 2026

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$83 nightly

$94 total

Feb 22 - Feb 23

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! (1,005 reviews)

Staff-clean room

Reviewed on Feb 8, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$162 nightly

$185 total

Feb 22 - Feb 23

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! (1,006 reviews)

Clean comfortable room!

Reviewed on Feb 8, 2026

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$203 nightly

$232 total

Feb 22 - Feb 23

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! (901 reviews)

Very welcoming and room very clean.

Reviewed on Jan 4, 2026

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$169 nightly

$193 total

Feb 15 - Feb 16

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! (1,000 reviews)

Great!!

Reviewed on Jan 26, 2026

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

$125 nightly

$137 total

Feb 24 - Feb 25

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 ...

8.4/10 Very Good! (1,001 reviews)

Nice staff

Reviewed on Feb 7, 2026

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$179 nightly

$199 total

Feb 16 - Feb 17

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! (434 reviews)

Amazing rooms and service!

Reviewed on Jan 17, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$459 nightly

$505 total

Feb 13 - Feb 14

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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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.

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.