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 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.

1. The Wildset

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

Sarah

SAR 860

SAR 1,039 total

includes taxes & fees

3 Nov - 4 Nov

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

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 1,926

SAR 2,118 total

includes taxes & fees

3 Nov - 4 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 726

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 rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

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 334

SAR 368 total

includes taxes & fees

8 Oct - 9 Oct

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.

5. The Oaks Waterfront

5.5 km from St. Michaels Winery

Jeffrey

SAR 1,652

SAR 1,817 total

includes taxes & fees

7 Oct - 8 Oct

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

A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.

6. Hummingbird Inn

13.1 km from St. Michaels Winery

Ann

SAR 1,112

SAR 1,266 total

includes taxes & fees

7 Oct - 8 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.

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

A hotel with a covered entrance, multiple floors, and a parking lot.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

7. Fairfield Inn & Suites by Marriott Easton

14.3 km from St. Michaels Winery

Amanda

SAR 507

SAR 558 total

includes taxes & fees

11 Oct - 12 Oct

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 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.

8. Best Western Plus Easton Inn & Suites

14.2 km from St. Michaels Winery

Lori

SAR 484

SAR 533 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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

A waterfront bar with outdoor seating, a view of the water, and American flags.

9. Sandaway Suites & Beach

10.7 km from St. Michaels Winery

Amber

SAR 1,013

SAR 1,115 total

includes taxes & fees

7 Oct - 8 Oct

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

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

A modern lounge area with a fireplace, seating, and a view of the outdoors.

A large building with a swimming pool, dock, and green surroundings.

10. The Tilghman Island Inn

12.1 km from St. Michaels Winery

William

SAR 694

SAR 764 total

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

11. Hampton Inn Easton

14 km from St. Michaels Winery

Rachel

SAR 480

SAR 528 total

includes taxes & fees

29 Oct - 30 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.

12. Holiday Inn Express Easton by IHG

14.1 km from St. Michaels Winery

Emily

SAR 503

SAR 553 total

includes taxes & fees

25 Oct - 26 Oct

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.

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.

13. The Tidewater Inn

12.8 km from St. Michaels Winery

Miriam

SAR 625

SAR 687 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

14. Wylder Tilghman Island

12.6 km from St. Michaels Winery

Gary

SAR 821

SAR 1,091 total

includes taxes & fees

25 Oct - 26 Oct

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.

15. Baymont by Wyndham Easton

14.1 km from St. Michaels Winery

Ellen

SAR 334

SAR 368 total

includes taxes & fees

7 Oct - 8 Oct

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.

16. Econo Lodge Easton Route 50

14.1 km from St. Michaels Winery

Adriana

SAR 304

SAR 334 total

includes taxes & fees

12 Oct - 13 Oct

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Compare popular hotels close to St. Michaels Winery

Property	Property class	Guest rating
The Wildset	9.8 Exceptional 518 reviews	View
Inn at Perry Cabin	9.6 Exceptional 405 reviews	View
George Brooks House B&B	8.8 Excellent 78 reviews	View
St Michaels Inn	8.0 Very good 1,000 reviews	View
The Oaks Waterfront	10.0 Exceptional 44 reviews	View

Top St. Michaels Winery Hotel Reviews

Holiday Inn Express Easton by IHG

10/10 Excellent

"Clean, cost effective"

Best Western Plus Easton Inn & Suites

8/10 Good

"Very good location, there was variety at breakfast and the food and coffee very good. The room was in very good condition; there was not enough lighting in the room or bathroom. The toilet paper and tissues were very cheap. Overall our experience was very good and we enjoyed our stay."

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

Baymont by Wyndham Easton

10/10 Excellent

"Great"

The Tilghman Island Inn

10/10 Excellent

"I thoroughly enjoyed our stay at The Tilghman Island Inn. It is exceptionally clean and well maintained. The staff was friendly and helpful. Our room was on the waterfront side and the view was beautiful."

Inn at Perry Cabin

10/10 Excellent

"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."

Hummingbird Inn

10/10 Excellent

"Everyone here made us feel so welcomed! Beautiful property and our room was immaculate! The bar downstairs was such a great place to wind down and the wrap around porch was so inviting! Breakfast was delicious and the town was walkable with great shops and restaurants. 10 out of 10! We will be back!"

Hampton Inn Easton

10/10 Excellent

"Good place all in all"

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

10/10 Excellent

"This property is amazing! The pictures honestly didn't do it justice. The views, the house, the pool, all were incredible. Oh yes and the beautiful decor, the artwork by Michelle. Definitely the nicest place we've ever stayed in. The kids and adults all had a blast! Thank you so much, Paul and Michelle. Wonderful vacation"

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 334

Change your mind

Treat yourself

Be picky

Check prices for these dates

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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. Best Western Plus Easton Inn & Suites

9. Sandaway Suites & Beach

10. The Tilghman Island Inn

11. Hampton Inn Easton

12. Holiday Inn Express Easton by IHG

13. The Tidewater Inn

14. Wylder Tilghman Island

15. Baymont by Wyndham Easton

16. Econo Lodge Easton Route 50

Compare popular hotels close to St. Michaels Winery

Top St. Michaels Winery Hotel Reviews

Holiday Inn Express Easton by IHG

Best Western Plus Easton Inn & Suites

St Michaels Inn

Baymont by Wyndham Easton

The Tilghman Island Inn

Inn at Perry Cabin

Hummingbird Inn

Hampton Inn Easton

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

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