Hotels in St. Michaels

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Oct 17 - Oct 18
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Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Where to stay in St. Michaels?

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 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 1 - Nov 2
St Michaels Inn
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
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 27 - Oct 28
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 marina with multiple boats docked during sunset.
A historic brick building with a red roof, multiple windows, and a central staircase.
A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

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 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.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

4. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
$531
$584 total
includes taxes & fees
Nov 3 - Nov 4
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 two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

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 living room with a fireplace, a sofa, a chair, and a bookshelf.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

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 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.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
$489
$538 total
includes taxes & fees
Oct 18 - Oct 19
The Oaks Waterfront
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
A modern living room with a sofa, armchairs, a coffee table, and a fireplace.
A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.
A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

8. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
$111
$126 total
includes taxes & fees
Oct 19 - Oct 20
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.
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.
A cozy room with a fireplace, a framed picture above it, and two armchairs.

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 sandy beach, and a clear blue sky.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$190
$244 total
includes taxes & fees
Nov 10 - Nov 11
Hyatt Regency Chesapeake Bay
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.
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".

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 modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

12. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
$106
$121 total
includes taxes & fees
Nov 15 - Nov 16
Crowne Plaza Annapolis by IHG
A lakeside view with sailboats, grassy areas, and white Adirondack chairs.
A beach with clear water, sandy shore, and some vegetation.
A waterfront bar with outdoor seating, a view of the water, and American flags.
A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

13. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
$314
$346 total
includes taxes & fees
Nov 17 - Nov 18
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 bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.
A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.

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 with a brick facade, multiple parking spaces, and a landscaped area with trees.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

15. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$119
$131 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
A marina with boats docked at wooden piers, surrounded by greenery.
A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.
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.

16. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
$150
$165 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.
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.

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 hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.
A swimming pool with a tiled edge, wooden chairs, and tables around it.
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.
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.
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

19. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135
$149 total
includes taxes & fees
Oct 25 - Oct 26
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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0°
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11°
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17°
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26°
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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 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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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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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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Saint Michaels Town Hall

Saint Michaels Town Hall is worth a pic or two when discovering 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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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

The Wildset

The Wildset

10/10 Excellent
"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!!"
Bonnie 2-night trip
Posted 16 hours ago
The Wildset
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 17 hours ago
Graduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"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!"
James 2-night trip
Posted 17 hours ago
Rod 'N' Reel Resort
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"my stay went very well. the room was very clean and pleasant. the staff helped me with a couple of items, and the breakfast staff in the restaurant was extremely friendly and helpful."
PATRICK 3-night trip
Posted 18 hours ago
DoubleTree by Hilton Hotel Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"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)."
Ben 2-night trip
Posted 19 hours ago
St Michaels Inn
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"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."
Lamont 3-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

8/10 Good
"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"
Andrea 3-night trip
Posted 4 days ago
Hilton Garden Inn Annapolis Downtown
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 5 days ago
Sonesta ES Suites Annapolis

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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