Search Hotels Near St. Michaels Winery, St. Michaels

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30 Dec - 31 Dec
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31 Dec - 1 Jan
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2 Jan - 4 Jan
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9 Jan - 11 Jan

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Our top choices for St. Michaels Winery hotels

Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi
The Wildset

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels, 0.8 km from St. Michaels Winery
9.8 out of 10, Exceptional, (411)
"Everything was lovely. "
United States
Erin
The price is Rp2.997.355
Rp3.665.481 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Wildset
Porch
Parsonage Inn

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels, 1 km from St. Michaels Winery
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is Rp2.846.650
Rp3.131.315 total
includes taxes & fees
5 Jan - 6 Jan 2026
Parsonage Inn
Exterior
George Brooks House B&B

George Brooks House B&B

George Brooks House B&B
3.0 star property
1.9 km from St. Michaels Winery
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is Rp2.568.564
Rp2.825.420 total
includes taxes & fees
1 Jan - 2 Jan 2026
George Brooks House B&B
Front of property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
1.9 km from St. Michaels Winery
8.2 out of 10, Very good, (1000)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is Rp1.684.212
Rp1.852.667 total
includes taxes & fees
5 Jan - 6 Jan 2026
St Michaels Inn
Porch
Hummingbird Inn

Hummingbird Inn

Hummingbird Inn
3.5 star property
13.1 km from St. Michaels Winery
10.0 out of 10, Exceptional, (86)
"The kindest most sweetest checkin"
United States
Nicole
Hummingbird Inn
View from property
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
14.3 km from St. Michaels Winery
9.6 out of 10, Exceptional, (368)
"Great hotel, very clean & quiet. "
United States
Janet
The price is Rp3.047.590
Rp3.352.349 total
includes taxes & fees
11 Jan - 12 Jan 2026
Fairfield Inn & Suites by Marriott Easton
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
14.2 km from St. Michaels Winery
9.2 out of 10, Wonderful, (1000)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is Rp1.992.655
Rp2.191.921 total
includes taxes & fees
31 Dec - 1 Jan 2026
Best Western Plus Easton Inn & Suites
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
14 km from St. Michaels Winery
9.0 out of 10, Wonderful, (555)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is Rp1.957.817
Rp2.153.565 total
includes taxes & fees
29 Jan - 30 Jan 2026
Hampton Inn Easton
Free daily buffet breakfast
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
14.1 km from St. Michaels Winery
9.0 out of 10, Wonderful, (593)
"We only stayed one night but it was perfect. The room was very clean, the beds were comfortable, and the staff were very nice. "
United States
Nancy
The price is Rp2.249.592
Rp2.474.551 total
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Inn Express Easton by IHG
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
12.6 km from St. Michaels Winery
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is Rp1.973.165
Rp2.907.262 total
includes taxes & fees
6 Jan - 7 Jan 2026
Wylder Tilghman Island
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
12.8 km from St. Michaels Winery
8.8 out of 10, Excellent, (843)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is Rp2.997.355
Rp3.297.090 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
14.1 km from St. Michaels Winery
7.6 out of 10, Good, (828)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is Rp1.423.325
Rp1.565.657 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn
Reception
Econo Lodge Easton Route 50

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
14.1 km from St. Michaels Winery
6.6 out of 10, (386)
"Staff was great"
United States
Andre
The price is Rp1.356.178
Rp1.491.796 total
includes taxes & fees
11 Jan - 12 Jan 2026
Econo Lodge Easton Route 50
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top St. Michaels Winery Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"The staff was excellent. I would like to give appreciation to Figi, for his service and pleasant demeanor. "
Alvin 2-night trip
Posted 8 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
The Wildset

The Wildset

10/10 Excellent
"Everything was outstanding, however the lot and handicap ramp were VERY ICY. We almost fell multiple times. Just a caution"
nichole 1-night trip
Posted 9 days ago
The Wildset

Hotels near other St. Michaels Winery attractions

Windon Distilling

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

Classic Motor Museum

You can spend an afternoon exploring the galleries in Classic Motor Museum during your trip to St. Michaels.
See properties

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 0.7 mi (1.1 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, Higgins Yacht Yard and Marina or Windon Distilling.