Explore top 2026 4 Star Hotels in St. Michaels

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Top St. Michaels 4 Star hotels

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

$111 total

per night

Sep 27 - Sep 28

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. ...

8.8/10 Excellent! (1,139 reviews)

"The staff was very helpful. Especially Jacob!"

Reviewed on Aug 30, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$175 total

per night

Sep 13 - Sep 14

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, ...

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Fully refundableReserve now, pay when you stay

$245 total

per night

Sep 7 - Sep 8

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 ...

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$226 total

per night

Sep 29 - Sep 30

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 ...

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

$288 total

per night

Sep 29 - Sep 30

This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's ...

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$203 total

per night

Sep 13 - Sep 14

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 ...

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$267 total

per night

Sep 28 - Sep 29

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! (484 reviews)

"The staff was 100% on spot. Extremely helpful and courteous. The property was amazing and impeccably clean and maintained."

Reviewed on Aug 29, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$538 total

per night

Sep 1 - Sep 2

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! (44 reviews)

"The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out ..."

Reviewed on Aug 5, 2026

Marvel's on the Creek

6230 Beverly Rd East New Market MD

Fully refundableReserve now, pay when you stay

$200 total

per night

Aug 31 - Sep 1

A hot tub, free self parking, and free newspapers are featured at this bed & breakfast. Guests will appreciate free perks like full breakfast and WiFi in public ...

10/10 Exceptional! (170 reviews)

"Debby was a wonderful hostess at this beautiful bed and breakfast. She was very friendly, accomidating and made you feel very welcome. She served a delicious breakfast and even shared a secret recipe with me. Her home is beautifully decorated while the waterfront view is breathtaking. I highly recommend ..."

Reviewed on Aug 23, 2026

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Cambridge MD

An outdoor pool is featured at this apartment, along with free WiFi in public areas and barbecue grills.

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4 Star Hotels St. Michaels

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 St. Michaels 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 St. Michaels 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 St. Michaels, 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 St. Michaels hotel reviews by fellow wanderers

Crowne Plaza Annapolis by IHG

4 out of 5

Posted 1 hour ago

Travelocity Verified Review

"Took awhile to receive additional towels and washcloths. No microwave in rooms. Plus. - Great location to eateries, mall, and downtown Annapolis"

A verified traveler stayed at Crowne Plaza Annapolis by IHG

St Michaels Inn

4 out of 5

Posted 2 days ago

Travelocity Verified Review

"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"

A verified traveler stayed at St Michaels Inn

George Brooks House B&B

4 out of 5

Posted 10 days ago

Travelocity Verified Review

"We enjoyed our stay but found a few things that could have been better. Our host (Will) was not present the first day and most likely did not know the coffee and tea bar had sour milk and no sugar. I took it upon myself to rummage around and find these things but I would have liked it better if they were there. Also, we had a scrap of toilet paper in our room and no refills so I had to find that as well. Small things but not a good first impression. Otherwise, the room was very comfortable, the pool was great and the breakfast was delicious."

A verified traveler stayed at George Brooks House B&B