A waterfront street lined with trees and a white building with a balcony.

Find Historic Hotels in St. Michaels, MD from CA $188

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Check availability on St. Michaels Historic Hotels

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Oct 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for St. Michaels historic hotels

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
A spacious indoor area with brick walls, multiple tables and chairs, and string lights.
A marina with multiple boats docked during sunset.
An aerial view of a coastal town with a marina, houses, and a bridge in the background.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Ashley
CA $122
CA $188 total
includes taxes & fees
Nov 1 - Nov 2
Historic Inns of Annapolis
Three birds perched on a wooden structure by the water.
A kitchen with a central island, white cabinets, and a dining area with a table and chairs.
KI Beach House has many Great Rooms for Mingling or just being by yourself.
A wooden deck with picnic tables and umbrellas, a covered seating area with chairs, and a house with large windows.

2. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
CA $1,139
CA $1,976 total
includes taxes & fees
Oct 6 - Oct 7
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.
A two-story house with a large front porch and a covered patio area.
A spacious kitchen with a central island, wooden cabinets, and a dining area with a table and chairs.
A cozy living room with a sofa, chairs, a coffee table, and a patterned rug.

3. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
CA $998
CA $1,796 total
includes taxes & fees
Oct 6 - Oct 7
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A wooden dock extending into a calm body of water with boats docked at the end.
A kitchen with wooden flooring, stainless steel appliances, a white door, and a white dining table with chairs.
A two-story house with a porch, a flag, and a welcome sign.
A modern living room with a white sofa, a coffee table, and a potted plant.

4. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Nancy N.
CA $306
CA $622 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 2br home w/ parking in downtown Annapolis
A dining table with a wine bottle, glasses, and a red bowl with a leaf pattern.
A calm waterfront with boats docked, a bridge in the background, and autumn foliage along the riverbank.
A living room with a TV, a dining area, and a kitchen in the background.
A cozy living room with a bed, a television, a coffee table, and a sofa.

5. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
United States
Jill R.
CA $485
CA $705 total
includes taxes & fees
Oct 18 - Oct 19
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Exterior detail
Dining
Room
Living area

6. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
United States
Brian L.
CA $532
CA $1,065 total
includes taxes & fees
Oct 7 - Oct 8
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
View all properties

Top St. Michaels Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Staff was nice. Location was great. But hotel is in desperate need of remodeling. I think it’s been about 30 years since they had one."
Nicole 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 3 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 3 days ago
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 5 days ago
Inn at Perry Cabin
Parsonage Inn

Parsonage Inn

8/10 Good
"The Parsonage Inn is one of the most unique buildings on the main street through St. Michael's. We stayed in a room that faced the main street and it was amazingly quiet with respect to traffic noise. The decor is very old timey ... cute, quaint, and definitely fits the picture of what a B&B is. Physical security is very good: our room had a deadbolt lock, and the front door had an automatic deadbolt with a keypad on the outside for access. I can't comment on the quality of the breakfast because we are late risers. I would definitely stay at the Parsonage Inn again."
Daniel 2-night trip
Posted 4 months ago
Parsonage Inn

Frequently asked questions

What should a history enthusiast expect from a trip to St. Michaels?
Significant historical sites 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 historically relevant hotels are there in St. Michaels?
St. Michaels is home to 58 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the most important 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 agenda are Saint Michaels Town Hall and St. Michaels Marina.
What is a historic hotel like in St. Michaels?
When you choose a historic hotel, you'll enjoy a vacation someplace that has an officially recognized national historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be transformed into a historic hotel provided that it has special significance. Traditional architecture and period features can be admired in the communal spaces and guestrooms of these historic hotels in St. Michaels, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
They are quite similar. The term "historic hotel" is more common in the U.S., while you'll often hear "heritage hotel" in Asia and Europe. Historic hotels tend to place more significance on the architecture and actual building. Heritage hotels draw their meaning mainly from the cultural value that the place has and how it inspired the community.
Do historic hotels in St. Michaels have modern facilities?
Yes. Every effort is made to preserve historic facades and treasured traditions, but interiors include modern conveniences and safety features. Guests can expect the usual amenities you'd find in a hotel such as private rooms with updated bathroom facilities, WiFi, and more. In St. Michaels, booking a historic hotel doesn't mean you're picking a place that's uncomfortable for guests or simply rundown.

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