Photo by Louise Johnson

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for St. Michaels cottages

14

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 NZ$948
includes taxes & fees
9 Nov - 10 Nov
Plum Point Cottage #14
A covered patio with a table and chairs, large windows, and an American flag.

2. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$776
includes taxes & fees
6 Nov - 7 Nov
Plum Point Cottage #17
Fire pit (2)

3. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is NZ$965
includes taxes & fees
6 Nov - 7 Nov
Plum Point Cottage #15
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 NZ$1,208
includes taxes & fees
8 Nov - 9 Nov
Secluded Cozy Cottage in Historic Downtown
A house with a red door, a small porch, and a view of a river with a bridge in the background.

5. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
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

A waterfront property with a grassy lawn, white chairs, a dock, and a large building with multiple windows and a flag.
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?

Expect to pay between NZ$776 and NZ$1,208 per night for cottages in St. Michaels. No matter your budget, an excellent stay is only clicks away on Expedia. These prices were 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?

Choose from cottages in St. Michaels. No matter if you're holidaying with the family or organising a weekend escape with your besties, Expedia can help you find the right space to reconnect with nature.

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

After you've unpacked your bags and settled in, venture out and discover the cool things St. Michaels has for you to experience. St. Michaels Winery is a top attraction to add to your to-do list.

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