A waterfront street lined with trees and a white building with a balcony.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for St. Michaels cottages

A covered porch with wooden flooring, two wicker chairs with cushions, a small table, and a potted plant.

1. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is ￥51,673
￥82,490 total
includes taxes & fees
Nov 1 - Nov 2
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.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A covered patio with a table and chairs, large windows, and an American flag.

3. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is ￥43,060
￥72,333 total
includes taxes & fees
Oct 27 - Oct 28
Plum Point Cottage #17
An outdoor dining area with a wooden table and chairs, a bottle of wine, and a vase of flowers.

4. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is ￥51,500
￥90,201 total
includes taxes & fees
Nov 1 - Nov 2
Plum Point Cottage #15
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, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is ￥79,255
￥129,021 total
includes taxes & fees
Nov 8 - Nov 9
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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Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"The good part: the rooms are indeed historic and the location is great - right across from the MD state house, in the heart of Annapolis. The bed was very comfy and the shower was good. That said, the room was pretty small (guess they had smaller rooms back in the day) and the windows fronted on to the street. So, luxury no, history yes. FWIW, we parked a few blocks away at the Hillman Garage and just walked everywhere from there."
John 1-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about St. Michaels

St. Michaels Cottages information

Number of reviews
125
Accommodation
97 Cottages
Lowest Price
￥72,333
Highest Price
￥129,021

Frequently asked questions

How much do cottages in St. Michaels cost?
Expect to pay between ￥72,333 and ￥129,021 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 97 cottages in St. Michaels. No matter if you're vacationing with the family or organizing 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.