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

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Check availability on St. Michaels Romantic Hotels

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for St. Michaels romantic hotels

A two-story building with a covered entrance and an American flag.
A hotel room with two beds, a chair, and a painting on the wall.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

1. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Lynn
Rp1.593.286
Rp1.752.616 total
includes taxes & fees
5 Oct - 6 Oct
St Michaels Inn
A room with a view of a wooden deck and a gazebo by the water.
A hotel room with a large bed, a chair, a desk, and a television.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A golf course with a water hazard and surrounding trees.

2. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
Rp9.173.466
Rp10.090.813 total
includes taxes & fees
26 Oct - 27 Oct
Inn at Perry Cabin
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A large building with a swimming pool, dock, and green surroundings.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
A spacious indoor dining area with large windows, tables, and chairs.

3. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
United States
William
Rp3.308.170
Rp3.638.987 total
includes taxes & fees
5 Oct - 6 Oct
The Tilghman Island Inn
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

4. The Tidewater Inn

The Tidewater Inn
Easton
United States
Miriam
Rp3.200.878
Rp3.520.966 total
includes taxes & fees
1 Nov - 2 Nov
The Tidewater Inn
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A waterfront bar with outdoor seating, a view of the water, and American flags.
A beach with clear water, sandy shore, and some vegetation.
A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.

5. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
United States
Amber
Rp5.363.937
Rp5.900.330 total
includes taxes & fees
4 Nov - 5 Nov
Sandaway Suites & Beach
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
United States
Jeffrey
Rp7.869.868
Rp8.656.855 total
includes taxes & fees
5 Oct - 6 Oct
The Oaks Waterfront
A large, two-story barn-style building with a covered front porch and a garage.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

7. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
Rp2.880.790
Rp3.806.157 total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.
A group of people toasting at a round table in a room with large windows and artwork on the walls.
A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.
A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.

8. Hummingbird Inn

Hummingbird Inn
Easton
United States
Ann
Rp5.294.860
Rp6.028.201 total
includes taxes & fees
5 Oct - 6 Oct
Hummingbird Inn
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

9. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
United States
John
Rp3.504.872
Rp4.831.000 total
includes taxes & fees
18 Oct - 19 Oct
Hyatt Regency Chesapeake Bay
View all properties

Top St. Michaels Hotel Reviews

Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Check in was fast and easy. Front desk was helpful. Plenty of food and"
Ione 1-night trip
Posted 1 day ago
Best Western 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
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 13 days ago
The Westin Annapolis

Frequently asked questions

Searching for romantic hotels in St. Michaels?
Are you and your partner in need of a romantic getaway? Our guests also enjoy St. Michaels for its historic landmarks, shopping and seafood restaurants. If you want to explore the area, you might head to St. Michaels Marina, Chesapeake Bay Maritime Museum or St. Michaels Winery. If you're interested in staying near a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to St. Michaels?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in St. Michaels: The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for St. Michaels is 1341 mm.
What is there to do in St. Michaels?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that St. Michaels has to offer. Couples looking for a little of everything will enjoy St. Michaels for its historic landmarks, shopping and seafood restaurants. You might think about visiting St. Michaels Marina, Chesapeake Bay Maritime Museum or St. Michaels Winery.
What's the best way to get to St. Michaels and around town during my romantic getaway?
These transportation options in St. Michaels might help your romantic trip get off to a smooth start: To get to St. Michaels, book a flight to Easton, MD (ESN-Easton - Newnam), which is the closest major airport, located 8.8 mi (14.1 km) from the city centre. If you'd like to explore around the area, you may want a rental car for your journey.

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