The Best Hotels Closest to St. Michaels Winery in St. Michaels for 2026

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Our top choices for St. Michaels Winery hotels

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 dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

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.

1. The Wildset

Downtown St. Michaels, 0.8 km from St. Michaels Winery

Sarah

SAR 860

SAR 1,040 total

includes taxes & fees

3 Nov - 4 Nov

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

Downtown St. Michaels, 1 km from St. Michaels Winery

Virgilio

SAR 1,927

SAR 2,119 total

includes taxes & fees

8 Nov - 9 Nov

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

3. George Brooks House B&B

1.9 km from St. Michaels Winery

Erin

SAR 727

SAR 799 total

includes taxes & fees

2 Nov - 3 Nov

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

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

4. St Michaels Inn

1.9 km from St. Michaels Winery

Lynn

SAR 321

SAR 353 total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

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

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.

5. The Oaks Waterfront

5.5 km from St. Michaels Winery

Jeffrey

SAR 1,653

SAR 1,818 total

includes taxes & fees

13 Oct - 14 Oct

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

6. Hummingbird Inn

13.1 km from St. Michaels Winery

Ann

SAR 1,112

SAR 1,266 total

includes taxes & fees

19 Oct - 20 Oct

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.

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

7. Fairfield Inn & Suites by Marriott Easton

14.3 km from St. Michaels Winery

Amanda

SAR 508

SAR 558 total

includes taxes & fees

18 Oct - 19 Oct

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 covered patio area with wicker furniture and a view of a building with large windows.

8. Knapps Narrows Marina & Inn

11.7 km from St. Michaels Winery

BARBARA

SAR 563

SAR 620 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 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.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

9. Best Western Plus Easton Inn & Suites

14.2 km from St. Michaels Winery

Lori

SAR 484

SAR 533 total

includes taxes & fees

13 Oct - 14 Oct

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 waterfront property with a dock, a sailboat, and a building with a red roof.

A spacious indoor dining area with large windows, tables, and chairs.

10. The Tilghman Island Inn

12.1 km from St. Michaels Winery

William

SAR 695

SAR 764 total

includes taxes & fees

19 Oct - 20 Oct

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

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

10.7 km from St. Michaels Winery

Amber

SAR 1,127

SAR 1,239 total

includes taxes & fees

22 Oct - 23 Oct

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

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

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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

12. Hampton Inn Easton

14 km from St. Michaels Winery

Rachel

SAR 480

SAR 528 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

13. Holiday Inn Express Easton by IHG

14.1 km from St. Michaels Winery

Emily

SAR 560

SAR 616 total

includes taxes & fees

18 Oct - 19 Oct

A waterfront property with a covered patio, a dock, and a boat.

A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

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

A waterfront hotel with a covered dock and a large building with multiple balconies.

14. Wylder Tilghman Island

12.6 km from St. Michaels Winery

Gary

SAR 843

SAR 1,115 total

includes taxes & fees

14 Oct - 15 Oct

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 bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

15. The Tidewater Inn

12.8 km from St. Michaels Winery

Miriam

SAR 625

SAR 688 total

includes taxes & fees

2 Nov - 3 Nov

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

A gym with a treadmill, elliptical, and stationary bike.

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

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

16. Baymont by Wyndham Easton

14.1 km from St. Michaels Winery

Ellen

SAR 335

SAR 368 total

includes taxes & fees

13 Oct - 14 Oct

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

A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

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

A building with a sign reading "EcoLodge."

17. Econo Lodge Easton Route 50

14.1 km from St. Michaels Winery

Adriana

SAR 304

SAR 335 total

includes taxes & fees

18 Oct - 19 Oct

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Compare popular hotels close to St. Michaels Winery

Property	Property class	Guest rating
The Wildset	9.8 Exceptional 520 reviews	View
Inn at Perry Cabin	9.6 Exceptional 406 reviews	View
George Brooks House B&B	8.8 Excellent 78 reviews	View
St Michaels Inn	8.0 Very good 1,005 reviews	View
The Oaks Waterfront	10.0 Exceptional 44 reviews	View

Top St. Michaels Winery Hotel Reviews

Best Western Plus Easton Inn & Suites

10/10 Excellent

"We only stayed one night, but everything was great!"

St Michaels Inn

10/10 Excellent

"na"

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

The Tidewater Inn

10/10 Excellent

"Great restaurant. Helpful staff. Great location."

Holiday Inn Express Easton by IHG

10/10 Excellent

"Clean, cost effective"

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10/10 Excellent

"The house and grounds are beautiful, we loved the open floor plan . There was plenty of room for our group . We were visiting during the nor’easter so didn’t get a chance to swim , but it looked inviting! Hope to stay again , it’s a great place to visit with family and friends ."

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

10/10 Excellent

"Overall our stay was excellentThe air conditioning worked well downstairs, but the fan needs to be set to on and the temperature reduced to cool down upstairsThe older front of the house is furnished withLovely antiques so we mostly used the kitchen and family room in the backIt has a large yard for walking your dogBut was not enclosed along the back or one side so keep an eye on your petIce maker did not work but ice trays were provided and worked fineWe ate all meals outPark and harbor were right outside the front door, and many restaurants and shops were within easy walking distance of less than 1000 ftParked the cars on arrival and never moved them until we leftThe house is over 200 years old, the stairs to both upstairs areas were historically challenging and memorable. The back stairway was much easier to navigate than the frontHouse could use a little TLCHost quickly addressed a minor issue we had on arrival. would recommend labeling parking areas for which address they were forCell service is a bit spotty in the areaBut worked much better with wifi calling from the houseTelevision in family room worked fairly wellTelevision in master did not get any channelsNever found the pool?Had a nice 3 day stay"

Hampton Inn Easton

10/10 Excellent

"Good place all in all"

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."

Other attractions near St. Michaels Winery

Windon Distilling

You can take time to visit Windon Distilling during your travels to St. Michaels.

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Classic Motor Museum

You can spend an afternoon exploring the galleries in Classic Motor Museum during your travels in St. Michaels.

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St. Michaels Museum

8.6/10 (9 reviews)

You can browse the exhibits at St. Michaels Museum, a museum with a storied past, during your trip to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.

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Saint Marys Square

Saint Marys Square is just one of the places to see in St. Michaels, so why not enjoy the other things to explore during your travels?

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Saint Marys Square Museum

You can spend time studying the exhibits at Saint Marys Square Museum in St. Michaels.

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Back Creek Park

After visiting Back Creek Park, make a plan to see the other sights and activities in St. Michaels.

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Church Cove Park

Explore the great outdoors at Church Cove Park, a lovely green space in St. Michaels.

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Muskrat Park

After visiting Muskrat Park, make a plan to see the other sights and activities in St. Michaels.

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Frequently asked questions

What's the area like around St. Michaels Winery?

St. Michaels Winery is located in an area of St. Michaels known for its interesting historical sites. If you're looking for a convenient place to stay, check out the 29 hotels and other accommodations you'll find within a mile.

What's the best place to stay near St. Michaels Winery?

Inn at Perry Cabin is one of the top choices for your stay based on our traveler data, and this hotel offers a marina and a full-service spa. It's located just a short 0.6 mi (1 km) from St. Michaels Winery. Other good choices within a short distance include The Wildset and Parsonage Inn.

How many hotels will I be able to find close to St. Michaels Winery?

Expedia has 29 hotels and other accommodations within a mile from St. Michaels Winery.

If I need to cancel the hotel reservation for my stay near St. Michaels Winery, will I receive a refund?

Yes! Most hotel reservations are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Add dates, click "Search", then filter by "fully refundable" to view the best options available near St. Michaels Winery.

Where can I learn more about changing or cancelling my trip in the area near St. Michaels Winery?

For more details about picking new dates or cancelling your stay near St. Michaels Winery, go to https://www.expedia.com/service/.

What can I see and do near St. Michaels Winery?

You'll want to browse the exhibits at Chesapeake Bay Maritime Museum and St. Michaels Museum. You might spend a leisurely day outdoors at Church Cove Park and CL Open Field. If you have some time to wander around the area, you might stop by St. Michaels Marina, St Michaels Nature Trail, or Windon Distilling.

Find hotels near St. Michaels Winery, St. Michaels from SAR 335

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Our top choices for St. Michaels Winery hotels

1. The Wildset

2. Inn at Perry Cabin

3. George Brooks House B&B

4. St Michaels Inn

5. The Oaks Waterfront

6. Hummingbird Inn

7. Fairfield Inn & Suites by Marriott Easton

8. Knapps Narrows Marina & Inn

9. Best Western Plus Easton Inn & Suites

10. The Tilghman Island Inn

11. Sandaway Suites & Beach

12. Hampton Inn Easton

13. Holiday Inn Express Easton by IHG

14. Wylder Tilghman Island

15. The Tidewater Inn

16. Baymont by Wyndham Easton

17. Econo Lodge Easton Route 50

Compare popular hotels close to St. Michaels Winery

Top St. Michaels Winery Hotel Reviews

Best Western Plus Easton Inn & Suites

St Michaels Inn

Baymont by Wyndham Easton

The Tidewater Inn

Holiday Inn Express Easton by IHG

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Hampton Inn Easton

George Brooks House B&B

Other attractions near St. Michaels Winery

Windon Distilling

Classic Motor Museum

St. Michaels Museum

Saint Marys Square

Saint Marys Square Museum

Back Creek Park

Church Cove Park

Muskrat Park

Frequently asked questions