St. Michaels Holiday Rentals, Maryland: Private House Rentals

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

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Our top choices for St. Michaels hotels

A two-story building with a covered entrance and an American flag.

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

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

Lynn

2.458.890 ₫

2.704.778 ₫ total

includes taxes & fees

23 Sept - 24 Sept

A two-story house with a porch, a front door, and a small garden area.

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.

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.

2. The Wildset

Downtown St. Michaels

Sarah

6.218.780 ₫

7.491.158 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

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.

3. George Brooks House B&B

St. Michaels

Erin

5.503.230 ₫

6.053.553 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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.

4. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

15.690.060 ₫

17.259.066 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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 room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

5. Best Western Plus Easton Inn & Suites

Easton

Raheem

3.356.580 ₫

3.692.238 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A kitchen with a stone wall, a microwave, and various food items on the counter.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.

A residential area with a large building, a swimming pool, and well-maintained lawns.

6. Baymont by Wyndham Easton

Easton

Erik

2.552.822 ₫

2.808.104 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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 indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

7. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

3.516.603 ₫

3.868.264 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A marina with boats docked at wooden piers, surrounded by greenery.

A waterfront property with houses, a dock, and a grassy area.

A building with a sign reading "The Inn."

A bed with two pillows, one with "HAPPY PLACE" text, and a framed picture above the bed.

8. Knapps Narrows Marina & Inn

Sherwood

BARBARA

3.902.250 ₫

4.292.475 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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 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.

9. The Tidewater Inn

Easton

Miriam

5.177.980 ₫

5.695.778 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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 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.

10. The Oaks Waterfront

Easton

Jeffrey

11.451.402 ₫

12.596.542 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A grassy area with white Adirondack chairs and a view of sailboats on the water.

A beach with clear water, sandy shore, and some vegetation.

A large, two-story house with a balcony, situated on a grassy lawn with autumn leaves, near a body of water.

A bottle of Merlot wine and two glasses on a wooden tray by a window overlooking a lake.

11. Sandaway Suites & Beach

Oxford

Amber

7.024.605 ₫

7.727.066 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A hotel room with two beds, a desk, a TV, and a window with curtains.

A building with a sign reading "EcoLodge."

A covered corridor with a series of doors, each marked with a number.

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

12. Econo Lodge Easton Route 50

Easton

Brady

2.107.360 ₫

2.318.097 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

A restaurant with a counter, seating area, and a clock on the wall.

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

13. Best Western Kent Narrows Inn

Grasonville

Joshua

3.026.907 ₫

3.359.866 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

14. Holiday Inn Express Easton by IHG

Easton

Emily

3.876.980 ₫

4.264.678 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

15. Hampton Inn Easton

Easton

Rachel

3.840.032 ₫

4.223.827 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A modern kitchen with a large island, pendant lights, and a view to the outside.

A row of white single-story houses with dark roofs, a paved driveway, and a grassy lawn.

A covered outdoor seating area with tables and chairs, a pathway leading to it, and a landscaped garden.

A spacious living room with a sofa, coffee table, and dining area.

16. Queenstown Harbor Golf Resort

Queenstown

11.008.021 ₫

12.548.925 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.

A bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.

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.

17. Hummingbird Inn

Easton

Ann

7.704.522 ₫

8.771.602 ₫ total

includes taxes & fees

23 Sept - 24 Sept

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

A spacious lobby with a staircase, a reception desk, and a dining area.

18. Quality Inn Grasonville near Kent Island

Grasonville

John

2.602.000 ₫

2.888.220 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A large, two-story barn-style building with a covered front porch and a garage.

A large, two-story white house with a porch and multiple windows.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

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.

19. Kent Island Resort

Stevensville

Bethany

3.983.402 ₫

5.301.761 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

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.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

20. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

2.158.177 ₫

2.460.323 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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Where to stay in St. Michaels

Find the best St. Michaels areas for the activities you enjoy most.Learn more about St. Michaels

Downtown St. Michaels

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

Downtown St. Michaels

While visiting Downtown St. Michaels, you might make a stop by sights like St. Michaels Marina and Saint Michaels Town Hall.

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Stay near popular St. Michaels attractions

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

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)

Explore maritime heritage at this waterfront museum featuring the historic Hooper Strait Lighthouse and indigenous Chesapeake Bay watercraft. Watch shipwrights craft vessels while enjoying Miles River views.

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A white wooden house with a brown door and a small window.

Saint Michaels Village

This historic waterfront town showcases Maryland's maritime heritage through preserved colonial architecture. Explore the Maritime Museum or enjoy fresh seafood while watching sailboats glide across the harbour.

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St. Michaels Winery

8.6/10 (91 reviews)

Sample the Eastern Shore's finest wines in this historic Old Mill District winery. Enjoy guided tastings of 18 handcrafted varieties while learning about Maryland's unique terroir.

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1879 Hooper Straight Lighthouse

This rare screwpile lighthouse, relocated from Chesapeake Bay, offers a glimpse into 19th-century maritime life. Climb the spiral staircase to the lantern room for sweeping bay views and authentic keeper's quarters.

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St. Michaels Museum

8.6/10 (9 reviews)

Step into three restored 19th-century buildings that reveal the rich history of this Chesapeake Bay town. Explore exhibits on Frederick Douglass's local connections through walking tours of historic St. Michaels.

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Perry Cabin Park

This 9.5-acre community space offers well-maintained sports fields and a playground for active recreation. Enjoy a peaceful picnic in the pavilion or join a local baseball game in this serene St. Michaels gathering spot.

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St Michaels Nature Trail

You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.

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Windon Distilling

LYON RUM crafts small-batch American spirits in a historic St. Michaels mill using traditional methods. Sample their handcrafted rums in the welcoming tasting room while learning about their cane-to-glass process.

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Learn more about St. Michaels

Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living.

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Top St. Michaels Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"My North Tower King -Bay view room was very clean with modern furnishings and a beatiful balcony of the Bay. Unforunately, there was a refrigerator but there wasn't a micro wave in the room. The bathroom had a lovely shower, with modern fixtures with compatible for handicapped accessible persons but failed to have some of the basics, like hand/body soap and a bathroom ceiling fan necessary for clean, purified air in the bathroom and hotel room."

Graduate by Hilton Annapolis

10/10 Excellent

"Very nice decor and bed was comfortable . Classy looking place ."

Historic Inns of Annapolis

8/10 Good

"Superb location. Very tastefully treated. My only suggestions would be to provide more information regarding parking and a technology update in the rooms would be helpful. Plugs for charging was difficult as extensions and adapters were not reliable. High definition TV should be added as well. For the purposes of this trip, we enjoyed our stay very much."

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"The restaurant inside the hotel is a great idea. but the variety of food is very limited. But it is just my opinion."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"U"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"The property is located in an awesome location; convenient to shopping and restaurants. They do have a decent bar and restaurant in the hotel. The property was clean, parking was free and available, staff was great. We would definitely stay again."

Best Western Annapolis

10/10 Excellent

"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

More cheap stays in St. Michaels

Days Inn & Suites by Wyndham Cambridge

2917 Ocean Gateway Cambridge MD

1.658.775 ₫

1.841.240 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Best Western Annapolis

2520 Riva Rd Annapolis MD

1.943.954 ₫

2.216.108 ₫ total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (1,006 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.458.890 ₫

2.704.778 ₫ total

23 Sept - 24 Sept

includes taxes & fees

8/10 Very good! (1,001 reviews)

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD

2.539.032 ₫

2.894.496 ₫ total

30 Sept - 1 Oct

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

2.628.020 ₫

2.995.943 ₫ total

27 Sept - 28 Sept

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

3.026.907 ₫

3.359.866 ₫ total

29 Sept - 30 Sept

includes taxes & fees

8/10 Very good! (1,000 reviews)

Hotels in St. Michaels with star rating

Frequently asked questions

What's the seasonal weather 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.

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Book Hotels in St. Michaels on Expedia.com

Find hotels in St. Michaels, MD from 1.841.240 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in St. Michaels

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for St. Michaels hotels

1. St Michaels Inn

2. The Wildset

3. George Brooks House B&B

4. Inn at Perry Cabin

5. Best Western Plus Easton Inn & Suites

6. Baymont by Wyndham Easton

7. Fairfield Inn & Suites by Marriott Easton

8. Knapps Narrows Marina & Inn

9. The Tidewater Inn

10. The Oaks Waterfront

11. Sandaway Suites & Beach

12. Econo Lodge Easton Route 50

13. Best Western Kent Narrows Inn

14. Holiday Inn Express Easton by IHG

15. Hampton Inn Easton

16. Queenstown Harbor Golf Resort

17. Hummingbird Inn

18. Quality Inn Grasonville near Kent Island

19. Kent Island Resort

20. DoubleTree by Hilton Hotel Annapolis

Where to stay in St. Michaels

Downtown St. Michaels

Stay near popular St. Michaels attractions

Chesapeake Bay Maritime Museum

Saint Michaels Village

St. Michaels Winery

1879 Hooper Straight Lighthouse

St. Michaels Museum

Perry Cabin Park

St Michaels Nature Trail

Windon Distilling

Learn more about St. Michaels

Top St. Michaels Hotel Reviews

Rod 'N' Reel Resort

Graduate by Hilton Annapolis

Historic Inns of Annapolis

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Best Western Annapolis

The Westin Annapolis

More cheap stays in St. Michaels

Days Inn & Suites by Wyndham Cambridge

Best Western Annapolis

St Michaels Inn

Hampton Inn & Suites Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Hotels in St. Michaels with star rating

Frequently asked questions

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