Hotels near St. Michaels Winery

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Jul - 24 Jul
Tomorrow
24 Jul - 25 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels Near St. Michaels Winery

The Wildset
Relax in a spacious room with a large bed and sliding glass door leading to a balcony with a view.

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (341)
"At check in we were notified our room was upgraded for our anniversary. The room was beautiful, right within walking distance to restaurants, shopping and even the water. The included breakfast was great, staff was sweet, and property was just amazing! We would love to return! "
The price is S$305
includes taxes & fees
18 Aug - 19 Aug
The Wildset
Inn at Perry Cabin
Enjoy a romantic meal for two in our serene outdoor dining area, surrounded by a tranquil pool.

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Beautiful place to stay."
The price is S$913
includes taxes & fees
24 Jul - 25 Jul
Inn at Perry Cabin
Parsonage Inn
Experience the charm of this historic bed and breakfast, featuring a traditional gabled roof and wrap-around porch.

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is S$322
includes taxes & fees
20 Aug - 21 Aug
Parsonage Inn
George Brooks House B&B
Enjoy a relaxing stay in this two-story house with a spacious patio area and a swimming pool perfect for leisure activities.

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is S$342
includes taxes & fees
28 Jul - 29 Jul
George Brooks House B&B
St Michaels Inn
Stately building with a covered entrance and porch, set amidst a well-manicured lawn.

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Great spot to be close to town for a modest price. "
The price is S$159
includes taxes & fees
27 Jul - 28 Jul
St Michaels Inn
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is S$581
includes taxes & fees
20 Aug - 21 Aug
The Oaks Waterfront
Hummingbird Inn
Relax in this serene outdoor space with a view of the surrounding neighborhood.

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (76)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
Hummingbird Inn
The Tilghman Island Inn
Enjoy al fresco dining with a view of the water and a warm fire pit.

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (97)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is S$317
includes taxes & fees
30 Jul - 31 Jul
The Tilghman Island Inn
Sandaway Suites & Beach
Situated near a serene lake or sea, this two-story house offers a tranquil beachfront setting with a dock and lush surroundings.

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (142)
"It was such a beautiful place to stay at!! We only spent one night but definitely can see myself coming back with my family here! The view is to DIE for too!"
The price is S$403
includes taxes & fees
11 Aug - 12 Aug
Sandaway Suites & Beach
Fairfield Inn & Suites by Marriott Easton
Experience the warm welcome at this hotel, featuring a modern design with a brick and white exterior, a covered parking area and convenient entrance.

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (354)
"Very nice stay"
The price is S$208
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites by Marriott Easton
Best Western Plus Easton Inn & Suites
Relax in this elegantly furnished living area with a plush sofa, ornate mirror, and stone fireplace.

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Clean and great breakfast "
The price is S$181
includes taxes & fees
28 Jul - 29 Jul
Best Western Plus Easton Inn & Suites
Hampton Inn Easton
Classic brick facade with a prominent entrance and covered walkway.

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (520)
"Staff was very friendly"
The price is S$210
includes taxes & fees
30 Jul - 31 Jul
Hampton Inn Easton
The Tidewater Inn
Enjoy wine tastings and gatherings in this elegant corridor with tables and chairs, featuring a dedicated wine room.

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (806)
"Very nice hotel, beautiful lobby areas."
The price is S$238
includes taxes & fees
17 Aug - 18 Aug
The Tidewater Inn
Quality Inn
Stunning building with a brick and glass facade, featuring large windows and a flat roof, set amidst a beautifully manicured lawn with flowering bushes.

Quality Inn

2.5 star property
7.6 out of 10, Good, (750)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is S$130
includes taxes & fees
20 Aug - 21 Aug
Quality Inn
Econo Lodge Easton Route 50
Enjoy a casual dining experience with a view of the street outside.

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (367)
"The staff was VERY nice"
The price is S$120
includes taxes & fees
20 Aug - 21 Aug
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.

Top St. Michaels Winery Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"This was our fourth time staying here over the last year or two. It’s our favorite hotel in Annapolis."
Steve 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

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 28 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. Another good choice is The Wildset, located just 0.5 mi (0.8 km) away.

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

Expedia has 28 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 Higgins Yacht Yard and Marina.