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

$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! (1,010 reviews)

It was the best hotel we have stayed in, in a very long time. Loved it!!!

Reviewed on May 10, 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! (926 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

$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! (1,006 reviews)

Great location. Shower was challenging. Water was everywhere. We had to use the bath towels to clean up the water.

Reviewed on May 10, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

$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! (1,007 reviews)

No complaints!

Reviewed on May 10, 2026

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$162 nightly

$177 total

May 18 - May 19

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! (1,008 reviews)

Love it

Reviewed on May 7, 2026

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Fully refundableReserve now, pay when you stay

$275 nightly

$312 total

May 17 - May 18

Total with taxes and fees

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 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. Traveling on business? Take advantage of the 24-hour business ...

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

Marvel's on the Creek

6230 Beverly Rd East New Market MD

Fully refundableReserve now, pay when you stay

$182 nightly

$202 total

May 17 - May 18

Total with taxes and fees

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! (162 reviews)

See the river from rooms, patio, breakfast on the deck. Beautifully appointed rooms, lovely owner who is very accommodating and friendly. Excellent breakfast tailor- made to our needs. Perfect place to spend a weekend or longer.

Reviewed on May 8, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$489 nightly

$538 total

May 12 - May 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

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

Historic Inns of Annapolis

5 out of 5

Posted 1 hour ago

Travelocity Verified Review

"The only thing that was not 100% amazing was the toilet in our room was small and short and so was the shower head. I am only 5’4” so there is no way my husband would have been able to use either at 6’2”…. Other than that it was such an incredible historic place with all the grandeur and old wonderful charm!"

A verified traveler stayed at Historic Inns of Annapolis