The Best Hotels Closest to St. Michaels Winery in St. Michaels - 2026 Updated Prices

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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 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 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.

1. The Wildset

Downtown St. Michaels, 0.5 mi from St. Michaels Winery

Sarah

£217

includes taxes & fees

5 Oct - 6 Oct

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

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

2. Inn at Perry Cabin

Downtown St. Michaels, 0.6 mi from St. Michaels Winery

Virgilio

£426

includes taxes & fees

26 Oct - 27 Oct

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

A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

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

A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.

3. George Brooks House B&B

1.2 mi from St. Michaels Winery

Erin

£176

includes taxes & fees

29 Sept - 30 Sept

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

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

4. St Michaels Inn

1.2 mi from St. Michaels Winery

Lynn

£74

includes taxes & fees

4 Oct - 5 Oct

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 deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

5. The Oaks Waterfront

3.4 mi from St. Michaels Winery

Jeffrey

£365

includes taxes & fees

30 Sept - 1 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 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.

6. Hummingbird Inn

8.1 mi from St. Michaels Winery

Ann

£254

includes taxes & fees

29 Sept - 30 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.

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

8.9 mi from St. Michaels Winery

Amanda

£112

includes taxes & fees

4 Oct - 5 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 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.

8. Best Western Plus Easton Inn & Suites

8.8 mi from St. Michaels Winery

Raheem

£107

includes taxes & fees

29 Sept - 30 Sept

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

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

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

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

9. The Tilghman Island Inn

7.5 mi from St. Michaels Winery

William

£154

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

10. Sandaway Suites & Beach

6.6 mi from St. Michaels Winery

Amber

£250

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

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

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

11. Holiday Inn Express Easton by IHG

8.7 mi from St. Michaels Winery

Emily

£111

includes taxes & fees

25 Oct - 26 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

8.7 mi from St. Michaels Winery

Rachel

£124

includes taxes & fees

27 Oct - 28 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.

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

A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

13. The Tidewater Inn

8 mi from St. Michaels Winery

Miriam

£152

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

14. Wylder Tilghman Island

7.8 mi from St. Michaels Winery

Gary

£175

includes taxes & fees

29 Sept - 30 Sept

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

A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

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

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

15. Baymont by Wyndham Easton

8.8 mi from St. Michaels Winery

Ellen

£82

includes taxes & fees

29 Sept - 30 Sept

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

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.

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

16. Econo Lodge Easton Route 50

8.8 mi from St. Michaels Winery

Brady

£67

includes taxes & fees

4 Oct - 5 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 404 reviews	View
George Brooks House B&B	8.8 Excellent 78 reviews	View
St Michaels Inn	8.0 Very good 1,011 reviews	View
The Oaks Waterfront	10.0 Exceptional 44 reviews	View

Top St. Michaels Winery Hotel Reviews

Holiday Inn Express Easton by IHG

8/10 Good

"Hotel was nice…My only complaint was you can hear whomever was outside of your door or near your room…Other than that the stay was good."

Sandaway Suites & Beach

10/10 Excellent

"Loved staying here. The room had everything we needed & in the morning a lovely basket of breakfast treats & a carafe of coffee was left at our door. We'll definitely be returning."

The Tilghman Island Inn

10/10 Excellent

"Friendly people nice and clean Motel to stay in"

Baymont by Wyndham Easton

8/10 Good

"Staff was courteous and breakfast was adequate"

Wylder Tilghman Island

10/10 Excellent

"Everything exceeded expectations — particularly the staff — but the breakfast offering, which fell below."

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!"

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

10/10 Excellent

"Loved staying there and everything was so convenient!"

Private Peninsula Estate, Pool Houses, Crab Shack

10/10 Excellent

"Our 3 night stay in Neavitt was absolutely wonderful. The house and property were perfect for a small intimate wedding for our daughter. We made use of the kayaks, firepit and gas grill (gas provided). We decided to elevate our stay by having Chef Erica prepare the wedding night dinner. The food and table setting were perfect. Chef Erica and Pearl were the best! The house was exactly as listed. Even though we were prepared with toilet paper, paper towels, hand soap, etc. there was no need as all these items were provided. We arrived at the house to a fresh chocolate cake, tulips, and a nice card. The property was in close proximity to St. Michaels where we took a boat tour and had a delicious dinner at Theo's. Matt and Bruce were prompt in responding to my many questions throughout the process. I'd definitely stay at another property managed by these two. The only thing I would suggest is the purchase of additional paring knives."

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 trip to 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 travels 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 browsing 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, take a look at the 30 hotels and other accommodation options 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 traveller 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 find close to St. Michaels Winery?

Expedia has 30 hotels and other accommodation options 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 bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the filter option "fully refundable" to review the top deals on offer near St. Michaels Winery.

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, Windon Distilling or St Michaels Nature Trail.

Search Hotels Near St. Michaels Winery, St. Michaels

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

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. The Tilghman Island Inn

10. Sandaway Suites & Beach

11. Holiday Inn Express Easton by IHG

12. Hampton Inn Easton

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

Sandaway Suites & Beach

The Tilghman Island Inn

Baymont by Wyndham Easton

Wylder Tilghman Island

Hummingbird Inn

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Private Peninsula Estate, Pool Houses, Crab Shack

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