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 nightly

$126 total

Oct 19 - Oct 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 business center and free WiFi in public areas. ...

8.8/10 Excellent! (1,245 reviews)

"The staff are very nice. The room was clean but the hotel itself looked dirty and"

Reviewed on Oct 16, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

$147 nightly

$167 total

Oct 26 - Oct 27

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! (1,000 reviews)

"Clean room, very nice decor and great staff"

Reviewed on Oct 16, 2026

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Fully refundableReserve now, pay when you stay

$132 nightly

$146 total

Oct 27 - Oct 28

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! (1,004 reviews)

Reviewed on Oct 16, 2026

The Westin Annapolis

100 Westgate Cir Annapolis MD

Fully refundableReserve now, pay when you stay

$199 nightly

$227 total

Oct 25 - Oct 26

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 ...

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Fully refundableReserve now, pay when you stay

$215 nightly

$244 total

Nov 10 - Nov 11

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 ...

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

$223 nightly

$254 total

Nov 1 - Nov 2

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! (1,000 reviews)

"Perfect place to stay! Classy. Clean comfortable amazing staff"

Reviewed on Oct 15, 2026

The Inn at Chesapeake Bay Beach Club

180 Pier One Road Stevensville MD

Fully refundableReserve now, pay when you stay

$237 nightly

$263 total

Nov 15 - Nov 16

Total with taxes and fees

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! (503 reviews)

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Reviewed on Oct 15, 2026

The Oaks Waterfront

25876 Royal Oak Road Easton MD

Fully refundableReserve now, pay when you stay

$489 nightly

$538 total

Oct 18 - Oct 19

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! (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

$180 nightly

$200 total

Oct 19 - Oct 20

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! (175 reviews)

"Great place to take a break and enjoy wonderful views. Relaxed atmosphere and bountiful breakfast!"

Reviewed on Oct 16, 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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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

The Wildset

5 out of 5

Posted 8 hours ago

Travelocity Verified Review

"Loved my stay at Wildset. Place is very clean, cozy & comfortable. Staff very friendly. Convenience to everything in town. Only 2 issues I had was how long it took shower water to get hot. And it wasn’t super hot. Not sure if it was cause I was in main building. Other was a knocking noise which seemed to happen primarily while restaurant was open. Not sure if it was from the dishwasher or some other equipment. I’m a light sleeper too so some people may be able to sleep thru it. Would def stay here again!!"

A verified traveler stayed at The Wildset

Rod 'N' Reel Resort

5 out of 5

Posted 9 hours ago

Travelocity Verified Review

"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"

A verified traveler stayed at Rod 'N' Reel Resort

St Michaels Inn

4 out of 5

Posted 11 hours ago

Travelocity Verified Review

"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."

A verified traveler stayed at St Michaels Inn

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

5 out of 5

Posted 3 weeks ago

Travelocity Verified Review

"This was a great house right in the middle of town of Saint Michael’s that allowed us to walk to all the great restaurants in town plus have a parking place for our two cars. We had family staying at different places in town and we were able to come back to the large dining room area to finish out the night together."

A verified traveler stayed at Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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