Explore top 2026 4 Star Hotels in Shady Side

Name: The Inn at Chesapeake Bay Beach Club
Price range: $210 total
Rating: 9.4

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Top Shady Side 4 Star hotels

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$174 nightly

$198 total

Apr 19 - Apr 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 free WiFi in public areas, conference space, ...

9.4/10 Exceptional! (1,002 reviews)

Unique hotel in the heart of Annapolis. The room was lovely, comfortable and well equipped. Parking was a bit expensive $32 one day and strange, couldnt actually park in the covered garrage that was only for vallette patrons. Would have been nice to have a regular coffee maker in the room, only instant ...

Reviewed on Mar 27, 2026

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

$114 nightly

$129 total

Apr 12 - Apr 13

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! (1,005 reviews)

Clean room. Friendly staff.

Reviewed on Mar 25, 2026

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$229 nightly

$261 total

Apr 12 - Apr 13

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! (912 reviews)

I would have given an excellent but there was still some renovations being done. Staff was great, rooms were beautiful and clean. Location is perfect and within walking distance to tons of shops, restaurants and bars. Their restaurant was currently closed for remodeling but guests can still get room ...

Reviewed on Mar 20, 2026

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$89 nightly

$102 total

Apr 5 - Apr 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! (1,003 reviews)

Julie is amazing!

Reviewed on Mar 27, 2026

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$133 nightly

$146 total

Mar 30 - Mar 31

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! (1,006 reviews)

If we were staying in season it might have been a different experience (all outdoor amenities were not yet open), but it is a beautiful hotel and a great stay.

Reviewed on Mar 28, 2026

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$179 nightly

$204 total

Apr 5 - Apr 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! (1,001 reviews)

Love This hotel and the walking distance to everything

Reviewed on Mar 28, 2026

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$189 nightly

$210 total

Mar 30 - Mar 31

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! (442 reviews)

Our stay was absolutely Amazing. We dined at Knoxie’s table for dinner and enjoyed an evening in one of the private cabins. The property is beautiful and almost set up to be an all inclusive resort. The only thing missing was the golf course and a pool. The 2 things I would recommend are better toilet ...

Reviewed on Mar 24, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$489 nightly

$538 total

Mar 30 - Mar 31

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.