Photo by Louise Johnson

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for St. Michaels cottages

A porch with a door, a window, and a grill table with chairs.

1. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is AU$774
includes taxes & fees
14 Nov - 15 Nov
Plum Point Cottage #14
Fire pit (2)

2. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AU$814
includes taxes & fees
14 Nov - 15 Nov
Plum Point Cottage #15
A covered patio with a table and chairs, large windows, and an American flag.

3. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
Plum Point Cottage #17
A building with a black metal gate, a brick pathway, and greenery.

4. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is AU$1,045
includes taxes & fees
14 Nov - 15 Nov
Secluded Cozy Cottage in Historic Downtown
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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Learn more about St. Michaels

Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living.

See all hotels in St. Michaels
A lighthouse on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson
Open Photo by Louise Johnson

Top reviews in St. Michaels

An outdoor patio with tables and chairs, umbrellas, and a view of the water.
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels

10/10 Excellent

The Inn at Perry Cabin is a beautiful, luxurious hotel in a lovely setting. Our room was elegant and comfortable we had turn down service each night with cookies and slippers left for us. The staff is helpful and friendly. There are fresh flowers and plants throughout the hotel and the grounds are beautifully landscaped. The only negative is that they charge $50 a day to use the fitness facilities! Surprising at a very expensive hotel.
Australia
2revs
Reviewed April 17, 2015
Inn at Perry Cabin

Frequently Asked Questions

How much do cottages in St. Michaels cost?

Cottages in St. Michaels range between AU$774 and AU$1,045 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in St. Michaels?

Reconnect with nature in one of the cottages available in St. Michaels. To help you reserve an ideal property, make use of our handy filters to search for perks or amenities you need.

What is there to do in St. Michaels near my cottage?

Whatever your interests, St. Michaels has a whole lot to keep you occupied. St. Michaels Winery, Avalon Theatre and St. Michaels Museum are on many visitors' trip plans. You shouldn't miss Academy Art Museum, Academy of the Arts and Historical Society of Talbot County either. With Expedia's St. Michaels hotel deals, you can see even more fabulous attractions like these with the cash you save.