Historic Hotels & Resorts in St. Michaels from NZ$297

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Check availability on St. Michaels Historic Hotels

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Our top choices for St. Michaels historic hotels

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is NZ$337
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is NZ$297
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1907)
" Great place to stay!"
United States
Lewis
Historic Inns of Annapolis

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is NZ$697
includes taxes & fees
4 Jan - 5 Jan 2026
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (84)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is NZ$364
includes taxes & fees
4 Jan - 5 Jan 2026
Flag House Inn

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is NZ$545
includes taxes & fees
4 Jan - 5 Jan 2026
86 State Circle - Luxury Boutique Hotel

Charming Downtown 3rd Floor 1 Bedroom Apt

Charming Downtown 3rd Floor 1 Bedroom Apt
Historic District
9.8 out of 10, Exceptional, (20)
"We had a great time staying that this home. It was a perfect stay for my wife and I."
United States
Eric S.
The price is NZ$494
includes taxes & fees
29 Dec - 30 Dec
Charming Downtown 3rd Floor 1 Bedroom Apt

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (72)
"Great location!"
United States
Burton S.
The price is NZ$603
includes taxes & fees
20 Jan - 21 Jan 2026
Cozy 2br home w/ parking in downtown Annapolis

New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking
Historic District
10.0 out of 10, Exceptional, (34)
"This is our second stay here and we love it. Very clean and close to everything. "
United States
Francesca K.
The price is NZ$631
includes taxes & fees
29 Dec - 30 Dec
New Downtown Annapolis Condo With Free Parking

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is NZ$1,243
includes taxes & fees
6 Jan - 7 Jan 2026
Historic Row Home in Downtown Annapolis
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.

Top St. Michaels Hotel Reviews

Frequently asked questions

What should a history enthusiast expect from a trip to St. Michaels?
The historical places in St. Michaels are likely at the top of your travel itinerary. Visit the waterfront and shops while you're in town. During your stay in this romantic area, you can also relish a trip to the seafood restaurants.
How many historical hotels are there in St. Michaels?
St. Michaels is home to 65 lodging options bookable on Expedia though not many historic hotels to choose from.
What are the top historical places and other sights in St. Michaels?
St. Michaels is notable for landmarks like St. Michaels Museum. The picturesque setting of Church Cove Park and CL Open Field exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are St. Michaels Marina and Chesapeake Bay Maritime Museum.
What is a historic hotel like in St. Michaels?
Guests who book a historic hotel can spend a night or two in a place that has a national historic designation. A palace, castle, grand home or even an old police station, pub, lodge or skyscraper can be turned into a historic hotel provided that it's a place of special interest. Traditional architecture and period features can be admired in the public spaces and guestrooms of such hotels in St. Michaels, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
The two are similar. "Historic hotel" is a term often used in the US, whereas "heritage hotel" is common in Asia and Europe. A historic hotel tends to put more importance on the physical building and architecture. A heritage hotel draws meaning mainly from the cultural value and how it inspired the surrounding community.
Do historic hotels in St. Michaels have modern facilities?
Yes, every effort is made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Visitors should expect the popular amenities you'd get from a hotel such as Smart TVs, WiFi and updated bathroom facilities. When you book a historic hotel in St. Michaels, it doesn't mean you will stay in a place that's uncomfortable for guests or simply rundown.