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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for St. Michaels condo rentals

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

1. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
$325 nightly
The price is $345
Sep 30 - Oct 1
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
A modern lobby with a blue sofa, two framed abstract paintings, a potted plant, and a marble floor.

2. Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (4 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
$442 nightly
The price is $504
Oct 20 - Oct 21
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
A living room with a dining table, two sofas, a coffee table, and a patterned rug.

3. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
$430 nightly
The price is $486
Sep 30 - Oct 1
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy
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

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"The staff were super friendly."
Jim 1-night trip
Posted 12 hours ago
Courtyard by Marriott Annapolis

Find out more about St. Michaels

St. Michaels Condo Rentals information

Number of reviews
5
Accommodation
17 Condo Rentals
Lowest Price
$345
Highest Price
$486

Frequently asked questions

Why book your condo in St. Michaels with Expedia?
Vacationing should be a piece of cake, so if you're chasing condos at an affordable price, Expedia has you covered. Save those pennies and check in to something small and cozy, or splurge on a luxury condo and pamper your loved ones. Use our convenient search filters to secure a stay in St. Michaels that suits your needs.
How can I find cheap condos in St. Michaels?
With Expedia's handy filter tool, booking cheap condos in St. Michaels couldn't be simpler. To discover properties that are easy on your bank balance, fine-tune your search results by star rating, budget and amenities.
What is there to do in St. Michaels near my condo?
The ideal travel accessory is a well-planned to-do list. St. Michaels Winery is a wonderful place to kick off your sightseeing in St. Michaels.

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