Hotels in St. Michaels

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Oct 19 - Oct 20
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Oct 20 - Oct 21
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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 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.

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 salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A modern bar area with a long counter and multiple bar stools.

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 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.
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
$90
$137 total
includes taxes & fees
Nov 9 - Nov 10
Historic Inns of Annapolis
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.
A golf course with a water hazard and surrounding trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
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
$491
$540 total
includes taxes & fees
Nov 18 - Nov 19
Inn at Perry Cabin
A two-story house with a porch, a front door, and a small garden area.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.
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 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 dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A living room with a fireplace, a sofa, a chair, and a bookshelf.

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 white colonial-style house with a covered porch, brick steps, and outdoor seating.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
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 20 - Oct 21
The Oaks Waterfront
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.
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.
A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

8. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
$110
$125 total
includes taxes & fees
Oct 25 - Oct 26
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 four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.
An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.
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 spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A marina with boats docked, a sandy beach, and a clear blue sky.

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$146
$194 total
includes taxes & fees
Nov 18 - Nov 19
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 multi-story hotel with a brick facade, large windows, and an American flag.
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.

12. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
$105
$120 total
includes taxes & fees
Nov 16 - Nov 17
Crowne Plaza Annapolis by IHG
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 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.

13. Sandaway Suites & Beach

Sandaway Suites & Beach
Oxford
$302
$332 total
includes taxes & fees
Nov 18 - Nov 19
Sandaway Suites & Beach
A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.
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.
A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.

14. Hummingbird Inn

Hummingbird Inn
Easton
$329
$375 total
includes taxes & fees
Oct 20 - Oct 21
Hummingbird Inn
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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 building with a sign reading "The Inn."
A waterfront property with houses, a dock, and a grassy area.
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 20 - Oct 21
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 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 spacious atrium with a high ceiling, skylights, and a patterned floor.
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 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 Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

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 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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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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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
"Great location. Very clean."
scott 2-night trip
Posted 12 hours ago
St Michaels Inn
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Extremely spacious, nicely appointed room."
r 1-night trip
Posted 18 hours ago
Graduate by Hilton Annapolis
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 3 days ago
The Wildset
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 4 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 4 days ago
Annapolis Waterfront Hotel, Autograph Collection
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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