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

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.

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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 two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

8/10 Good

Expensive and basic
United Kingdom
Dina
Reviewed May 14, 2026
The Wildset

Frequently Asked Questions

How much do cottages in St. Michaels cost?

Expect to pay between and 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.