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

1. The Wildset

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

Tracey

AED 1,057 total

includes taxes & fees

19 Aug - 20 Aug

Premium bedding, down comforters, in-room safe, desk

2. Inn at Perry Cabin

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

Michel

AED 2,509 total

includes taxes & fees

23 Aug - 24 Aug

3. George Brooks House B&B

1.9 km from St. Michaels Winery

Erin

AED 855 total

includes taxes & fees

10 Aug - 11 Aug

4. St Michaels Inn

1.9 km from St. Michaels Winery

Karen

AED 346 total

includes taxes & fees

23 Aug - 24 Aug

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen

5. The Oaks Waterfront

5.5 km from St. Michaels Winery

Jeffrey

AED 1,778 total

includes taxes & fees

11 Aug - 12 Aug

6. Sandaway Suites & Beach

10.7 km from St. Michaels Winery

Rob

AED 1,091 total

includes taxes & fees

26 Aug - 27 Aug

7. Fairfield Inn & Suites by Marriott Easton

14.3 km from St. Michaels Winery

Stephanie

AED 546 total

includes taxes & fees

16 Aug - 17 Aug

8. The Tilghman Island Inn

12.1 km from St. Michaels Winery

Wm

AED 909 total

includes taxes & fees

9 Aug - 10 Aug

9. Best Western Plus Easton Inn & Suites

14.2 km from St. Michaels Winery

Margaret

AED 562 total

includes taxes & fees

9 Aug - 10 Aug

10. Wylder Tilghman Island

12.6 km from St. Michaels Winery

Leslie

AED 1,265 total

includes taxes & fees

1 Sep - 2 Sep

11. Hampton Inn Easton

14 km from St. Michaels Winery

Donald

AED 591 total

includes taxes & fees

9 Aug - 10 Aug

12. Holiday Inn Express Easton by IHG

14.1 km from St. Michaels Winery

Maura

AED 626 total

includes taxes & fees

9 Aug - 10 Aug

13. The Tidewater Inn

12.8 km from St. Michaels Winery

Diana

AED 680 total

includes taxes & fees

16 Aug - 17 Aug

14. Quality Inn

14.1 km from St. Michaels Winery

Karen

AED 409 total

includes taxes & fees

26 Aug - 27 Aug

15. Econo Lodge Easton Route 50

14.1 km from St. Michaels Winery

michael

AED 327 total

includes taxes & fees

12 Aug - 13 Aug

View all properties

Compare popular hotels close to St. Michaels Winery

Property	Property class	Guest rating
The Wildset	2.5 star property	9.8 Exceptional 492 reviews	View
Inn at Perry Cabin	5.0 star property	9.6 Exceptional 395 reviews	View
George Brooks House B&B	3.0 star property	8.8 Excellent 76 reviews	View
St Michaels Inn	2.5 star property	8.2 Very Good 1,002 reviews	View
The Oaks Waterfront	4.0 star property	10.0 Exceptional 44 reviews	View

Top St. Michaels Winery Hotel Reviews

Sandaway Suites & Beach

10/10 Excellent

"Beautiful property, friendly staff and I really enjoyed my stay!"

The Oaks Waterfront

10/10 Excellent

"The Oaks Waterfront was exactly the kind of getaway we were looking for. Tucked away in a quiet, secluded setting, it feels like you’re escaping from everything, yet St. Michaels is only a short ride away thanks to their beautiful shuttle. It really gives you the best of both worlds. What stood out most to us was the family-owned and operated feel. Everyone was genuinely friendly, and there was a warmth about the property that made it feel less like a hotel and more like staying with incredibly hospitable friends. It has a relaxed, welcoming atmosphere that makes it easy to settle in. We stayed in one of the cottages, and it was beautifully appointed with comfortable bedding and thoughtful touches that made it feel luxurious without trying too hard. The entire property is impeccably maintained, and you can tell the owners take great pride in every detail. We also traveled with our two dogs, and they were just as welcome as we were. They loved the cottage, and we appreciated the dog beds, bowls, and bottled water waiting for them. Those little touches made all the difference. The food was fresh and delicious, and the complimentary breakfast each morning was another example of the attention to detail they put into the guest experience. A special thank you to Kathie, Brad, Linda, and the entire team, including housekeeping. Their kindness and genuine hospitality are what make The Oaks such a special place."

St. Michaels Escape | Pool, Hot Tub & Fire Pit

10/10 Excellent

"This property is stunning. Our family had a wonderful time. The pool and hot tub are great and the view of the water is so beautiful. The location is also so nice. You’re only a few minutes from downtown St Michaels which is so nice . Also, communication with the property manager was so great. She was extremely helpful. We would absolutely come back here."

The Tilghman Island Inn

8/10 Good

"Just left Tilghman Island Inn after a a girl's trip stay. We had the best time. The grounds are beautiful, the room was cleam, bed was comfortable, the pool was so nice, and the morning pastries are delicious. We only wished we had a refrigerator in the room BUT it didn't really matter too much since we were close to the lounge and it was not a busy week. We would recommend this place to anyone and plan to come back again at some point."

The Tidewater Inn

8/10 Good

"The location was great and property was very well kept and accommodating. Staff was very friendly and helpful. Had a great dinner at restaurant on property. Room was comfortable but bathroom very tight with no counter space for use of toiletries. I know it is a historic property with limited space but that would be on my wish list to make getting ready much easier!"

Waterfront Escape with Pool Nature Lover Paradise

10/10 Excellent

"Very spacious property for a family of 14. Sleeping arrangements required a bit of creativity but everything worked out! Everyone had a great time by the pool and the property was very clean. Host was responsive and helpful during the stay!"

Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways

10/10 Excellent

"Jennifer, the host, was very responsive and answered all of my questions. The home was more than we expected. Our family was able to spread out and have their own space. The home was extremely clean. My grandkids stayed in the pool from morning to night, and my grandson enjoyed fishing from the dock. The cabinets and drawers were well stocked with everything you might need. There was a groundskeeper available for questions, which was convenient. We brought our boat, launched it from the Oxford Marina, and spent time on the water. We also had a photographer come to the property and take family pictures. We had a wonderful time, and I know my grandchildren will cherish the memories. The Baker family"

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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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 AED 327

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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. Sandaway Suites & Beach

7. Fairfield Inn & Suites by Marriott Easton

8. The Tilghman Island Inn

9. Best Western Plus Easton Inn & Suites

10. Wylder Tilghman Island

11. Hampton Inn Easton

12. Holiday Inn Express Easton by IHG

13. The Tidewater Inn

14. Quality Inn

15. Econo Lodge Easton Route 50

Compare popular hotels close to St. Michaels Winery

Top St. Michaels Winery Hotel Reviews

Sandaway Suites & Beach

Other attractions near St. Michaels Winery

Windon Distilling

Frequently asked questions