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 €472
includes taxes & fees
9 Nov - 10 Nov
Plum Point Cottage #14
A house with a red door, a small porch, and a view of a river with a bridge in the background.

2. 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.
The price is €434
includes taxes & fees
5 Nov - 6 Nov
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Fire pit (2)

3. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is €505
includes taxes & fees
5 Nov - 6 Nov
Plum Point Cottage #15
A covered patio with a table and chairs, large windows, and an American flag.

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is €410
includes taxes & fees
5 Nov - 6 Nov
Plum Point Cottage #17
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

5. 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 €611
includes taxes & fees
8 Nov - 9 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

Frequently Asked Questions

How much do cottages in St. Michaels cost?

Expect to pay between €409 and €610 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.

Why book your cottage in St. Michaels with Expedia?

Expedia has some superb cottages in St. Michaels, so start packing for a memorable stay close to nature. If you have a budget, select how much you want to spend and the star rating of your property. Or, make use of our filters to search for cottages with a hot tub or free WiFi. We'll help you find the perfect fit whatever your plans or bank balance.

How can I find cheap cottages in St. Michaels?

A wonderful way to get cheap cottages in St. Michaels is with Expedia's user-friendly filter tool. Refine your search by budget, amenities and star rating to snag awesome prices in just a few clicks.

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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