Hotels in St. Michaels

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Oct 12 - Oct 13
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Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Where to stay in St. Michaels?

A two-story building with a covered entrance and an American flag.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
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
$89
$98 total
includes taxes & fees
Nov 2 - Nov 3
St Michaels Inn
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.
A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

2. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
$161
$178 total
includes taxes & fees
Oct 20 - Oct 21
Rod 'N' Reel Resort
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
A historic brick building with a red roof, multiple windows, and a central staircase.
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.

3. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
$89
$136 total
includes taxes & fees
Nov 11 - Nov 12
Historic Inns of Annapolis
A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A hotel room with a large bed, a chair, a desk, and a television.

4. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
$513
$564 total
includes taxes & fees
Nov 8 - Nov 9
Inn at Perry Cabin
A two-story house with a porch, a front door, and a small garden area.
A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.
A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

5. The Wildset

The Wildset
Downtown St. Michaels
$229
$277 total
includes taxes & fees
Nov 3 - Nov 4
The Wildset
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

6. George Brooks House B&B

George Brooks House B&B
St. Michaels
$215
$237 total
includes taxes & fees
Nov 2 - Nov 3
George Brooks House B&B
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 deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
$489
$538 total
includes taxes & fees
Oct 14 - Oct 15
The Oaks Waterfront
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

8. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
$106
$121 total
includes taxes & fees
Oct 18 - Oct 19
DoubleTree by Hilton Hotel Annapolis
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.
A cozy room with a fireplace, a framed picture above it, and two armchairs.
An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.
A four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.

9. Parsonage Inn

Parsonage Inn
Downtown St. Michaels
$250
$275 total
includes taxes & fees
Nov 2 - Nov 3
Parsonage Inn
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
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.

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$180
$233 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Regency Chesapeake Bay
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

11. The Tidewater Inn

The Tidewater Inn
Easton
$179
$197 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

12. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
$105
$120 total
includes taxes & fees
Oct 25 - Oct 26
Crowne Plaza Annapolis by IHG
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.
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.

13. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
$300
$330 total
includes taxes & fees
Nov 11 - Nov 12
Sandaway Suites & Beach
A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.
A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.
A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.
A group of people toasting at a round table in a room with large windows and artwork on the walls.

14. Hummingbird Inn

Hummingbird Inn
Easton
$329
$375 total
includes taxes & fees
Oct 19 - Oct 20
Hummingbird Inn
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.

15. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129
$142 total
includes taxes & fees
Oct 14 - Oct 15
Best Western Plus Easton Inn & Suites
A marina with boats docked at wooden piers, surrounded by greenery.
A waterfront property with houses, a dock, and a grassy area.
A covered patio area with wicker furniture and a view of a building with large windows.
A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

16. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
$150
$165 total
includes taxes & fees
Oct 14 - Oct 15
Knapps Narrows Marina & Inn
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.
A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.
A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.
A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

17. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
$147
$167 total
includes taxes & fees
Oct 26 - Oct 27
Graduate by Hilton Annapolis
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

18. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
$91
$104 total
includes taxes & fees
Nov 9 - Nov 10
Country Inn & Suites by Radisson, Annapolis, MD
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.
A hotel with a covered entrance, multiple floors, and a parking lot.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

19. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135
$149 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
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Our prices for hotels in St. Michaels are cheapest in January
Price trends for hotels in St. Michaels
Pricing is based on two traveler single night rates
View properties in October
Typical weather for St. Michaels
October
High 19°C / low 13°C. Sunny most days.
View properties in October
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11°
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17°
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Monthly weather averages (˚C)

Top neighborhoods in St. Michaels

A coastal town with a marina, houses, and a forested landscape.

Downtown St. Michaels

The Downtown St. Michaels neighborhood offers attractions such as St. Michaels Marina and Saint Michaels Town Hall.

Top landmarks in St. Michaels

A lighthouse on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)
Chesapeake Bay Maritime Museum is just one of the attractions in Downtown St. Michaels, St. Michaels so you might want to stop by during your trip. If you want to experience more of the culture St. Michaels has to offer, head to 1879 Hooper Straight Lighthouse, Saint Michaels Town Hall, and St. Michaels Marina.
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A marina with several sailboats docked in calm waters.

St. Michaels Marina

You can stroll along St. Michaels Marina for relaxing water views when you're in Downtown St. Michaels. If you carry on walking you'll get to Higgins Yacht Yard and Marina for some more water views.
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A white wooden house with a brown door and a small window.

Saint Michaels Village

If you like shopping, take time out to go to Saint Michaels Village when in St. Michaels.
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St. Michaels Winery

8.6/10 (91 reviews)
Travelers to St. Michaels might want a tour of St. Michaels Winery in Downtown St. Michaels.
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1879 Hooper Straight Lighthouse

Downtown St. Michaels is home to 1879 Hooper Straight Lighthouse, so why not stop by during your stay in St. Michaels.
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Saint Michaels Town Hall

Saint Michaels Town Hall is worth a pic or two when discovering Downtown St. Michaels.
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St Michaels Nature Trail

Downtown St. Michaels is home to St Michaels Nature Trail, so why not stop by during your stay in St. Michaels.
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Perry Cabin Park

Perry Cabin Park is worth a visit, located 0.4 mi (0.7 km) from central St. Michaels.
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Learn more about St. Michaels

Along the Miles River, maritime heritage comes alive at the Chesapeake Bay Maritime Museum where working shipwrights still practice traditional boat building. The town's colonial-era streets lead to boutiques housed in buildings that have witnessed centuries of seafaring commerce. Take a sailing excursion on a historic skipjack, the traditional oyster-harvesting vessel that once defined the bay's economy. At waterfront restaurants, blue crabs arrive fresh from local watermen who've worked these waters for generations. St. Michaels Winery offers tastings in a converted mill, while the town museum reveals how this 'town that fooled the British' earned its Revolutionary War nickname. Church Cove Park provides peaceful water views where ospreys dive for dinner with remarkable precision.

See all hotels in St. Michaels
A lighthouse on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson

Check out reviews of St. Michaels hotels guests love

St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 1 hour ago
St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"The resort was beautiful and very well maintained, the staff were accommodating and went out of their way to make sure we had what we needed or asked for. My only negative would be to make access to links/online information for room service, and restaurant menus. I spent too much time trying to navigate to find these things based on the flyers I was given at check in. For visitors who are not computer savvy, this is very challenging. But other than that, would love to come and stay again."
Debra 1-night trip
Posted 11 hours ago
Hyatt Regency Chesapeake Bay
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Good stay , wish the hot tub worked"
Andrew 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Breakfast need to work on, it has nothing to eat then we have to go out buy breakfast. Everythingelse is good."
Thao 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."
Melissa 2-night trip
Posted 1 day ago
Rod 'N' Reel Resort
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"
Shannon 1-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
George Brooks House B&B

George Brooks House B&B

8/10 Good
"We enjoyed our stay but found a few things that could have been better. Our host (Will) was not present the first day and most likely did not know the coffee and tea bar had sour milk and no sugar. I took it upon myself to rummage around and find these things but I would have liked it better if they were there. Also, we had a scrap of toilet paper in our room and no refills so I had to find that as well. Small things but not a good first impression. Otherwise, the room was very comfortable, the pool was great and the breakfast was delicious."
Donna 2-night trip
Posted 2 months ago
George Brooks House B&B
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 hotels do travelers like in St. Michaels?
Guests like St Michaels Inn, Inn at Perry Cabin and The Wildset.
Can I book refundable accommodations in St. Michaels?
If you want the flexibility to change your plans to St. Michaels, most hotels offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where should I stay in St. Michaels if I want a cheap accommodation?
St Michaels Inn is an accommodation you might want to consider that'll save you money.
Where can I stay in St. Michaels if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, look over our selection of 35 vacation homes. You can also consider one of the 5 apartments or 9 cottages.
What will the weather in St. Michaels be like during my trip?
The warmest months in St. Michaels are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 41°F. The rainiest months are August and October.
Why should I book my St. Michaels hotel through Hotels.com?
There are plenty of reasons to book your St. Michaels travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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