Explore top 2026 4 Star Hotels in Shady Side

Name: The Inn at Chesapeake Bay Beach Club
Price range: $232 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

$181 nightly

$207 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! (1,008 reviews)

Excellent stay! Kitchen was fabulous - great food for breakfast! Will be back!

Reviewed on Apr 9, 2026

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

Fully refundableReserve now, pay when you stay

$106 nightly

$120 total

Apr 26 - Apr 27

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! (1,004 reviews)

Renovated and very clean.

Reviewed on Apr 10, 2026

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$229 nightly

$261 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 24-hour business center, free WiFi in public ...

8.8/10 Excellent! (916 reviews)

All restaurants onsite were not open! We had to order from a restaurant nearby but it really was not set up properly for room service. We had to go there to order and pickup and they were not really sure of the process for hotel guests so we just paid with a separate CC. Breakfast was essentially ...

Reviewed on Mar 29, 2026

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$109 nightly

$124 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 business center and free WiFi in public areas. ...

8.6/10 Excellent! (1,004 reviews)

It’s one of the few area hotels with a bar and restaurant. Staff was great. Room very clean and AC/HEATER was very quiet operating via thermostat. Bed was very comfortable and WiFi was bulletproof Breakfast must be paid for but parking is free. Would highly recommend.

Reviewed on Apr 8, 2026

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$156 nightly

$171 total

Apr 19 - Apr 20

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)

Make sure to request bay front room. These are great across the hall are views of heating units and walls.

Reviewed on Apr 7, 2026

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$189 nightly

$215 total

Apr 12 - Apr 13

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)

Beautiful hotel. Great location. Friendly staff.

Reviewed on Apr 7, 2026

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$209 nightly

$232 total

Apr 12 - Apr 13

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! (447 reviews)

Beautiful Boutique Hotel on the eastern shore right over the Bay bridge great restaurant Little market that’s amazing nice spa and very pretty and accommodating hotel would highly recommend it!

Reviewed on Apr 4, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$489 nightly

$538 total

Apr 12 - Apr 13

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.

Recent Shady Side hotel reviews by fellow wanderers

Comfort Inn Largo-Washington DC East

3 out of 5

Posted 2 hours ago

Travelocity Verified Review

"Staff: amazing and very helpful loved them Room: it was outdated and there were stains everywhere, it was clean but vents were full of dust in bathroom Stains on couch and marks on tables and bathroom tub chipping ONLY HAD ONE BLIND, very see through. The blind was also so marked up. Pool had weird looking sudds in it, decided to opt out Gym was also outdated, looks like everything hasn’t been changed in a long time Offered to change my room, so I’ll give credit for that but decided if I had to spend the one night in the room I’d just stay there all weekend."

A verified traveler stayed at Comfort Inn Largo-Washington DC East

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

1 out of 5

Posted 9 hours ago

Travelocity Verified Review

"The air condition was almost dangling from the wall. The toilet was clogged, half was converted to shared apartment to bring in profit to management, bedspread wasnt changed in 4 days, a lot of fighting in the complex, folks smoke weed everywhere. And yet they have the audacity to charged full rate as other hotels."

A verified traveler stayed at La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway