Explore top 2025 4 Star Hotels in St. Michaels

Name: The Inn at Chesapeake Bay Beach Club
Price range: $242 total
Rating: 9.4

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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

$106 nightly

$121 total

Nov 3 - Nov 4

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! (1,001 reviews)

"Comfortable place to stay, nice shopping area close by."

Reviewed on Sep 29, 2025

The Westin Annapolis

100 Westgate Cir, Annapolis, MD

Fully refundableReserve now, pay when you stay

$204 nightly

$233 total

Nov 2 - Nov 3

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! (999 reviews)

"Excellent hotel"

Reviewed on Sep 14, 2025

Hyatt Regency Chesapeake Bay

100 Heron Blvd, Cambridge, MD

Fully refundableReserve now, pay when you stay

$233 nightly

$265 total

Oct 8 - Oct 9

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 ...

8.6/10 Excellent! (1,002 reviews)

"Hyatt regency is more like a Hyatt place … fewer people working , in room dining is in paper boxes with plastic cutlery , but still regency pricing . But excellent pet policy and everyone so kind to pets"

Reviewed on Oct 3, 2025

Graduate by Hilton Annapolis

126 West St, Annapolis, MD

$184 nightly

$209 total

Oct 30 - Oct 31

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! (1,002 reviews)

"Very rude waitress at restaurant, very aloof and disinterested food and beverage manager. No compensation for disrespect and uncomfortable situation in restaurant. Otherwise, very comfortable room and pleasant front desk staff and valet."

Reviewed on Oct 3, 2025

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St, Annapolis, MD

Fully refundableReserve now, pay when you stay

$212 nightly

$241 total

Nov 2 - Nov 3

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! (870 reviews)

"Perfect location and beautiful views."

Reviewed on Oct 2, 2025

Rod 'N' Reel Resort

4165 Mears Ave, Chesapeake Beach, MD

$163 nightly

$179 total

Oct 14 - Oct 15

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 ...

8.2/10 Very Good! (1,001 reviews)

"Everything was so nice"

Reviewed on Oct 2, 2025

The Inn at Chesapeake Bay Beach Club

180 Pier One Road, Stevensville, MD

$218 nightly

$242 total

Nov 2 - Nov 3

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! (421 reviews)

"I've stayed at many hotels and this one.Tops them all with the dining menu and delicious food.That is offered. The accommodations are very comfortable."

Reviewed on Oct 3, 2025

The Oaks Waterfront

25876 Royal Oak Road, Royal Oak, Easton, MD

$459 nightly

$505 total

Oct 8 - Oct 9

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 ...

9.8/10 Exceptional! (38 reviews)

Get away

"Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?"

Reviewed on Sep 2, 2025

Marvel's on the Creek

6230 Beverly Rd, East New Market, MD

$188 nightly

$209 total

Oct 8 - Oct 9

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 ...

9.8/10 Exceptional! (159 reviews)

Wonderful stay at Marvels on the Creek

"Beautiful house and surrounding area. Very relaxing as it is by the water. Delicious breakfast with a lot of variety. The freshly baked sticky bun is to die for! Debbie is the perfect host. Very accommodating and so much fun to talk to! She is welcoming and makes you feel at home in her house. The ..."

Reviewed on Oct 5, 2025

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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.