Search and Rent St. Michaels Condos

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In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for St. Michaels condo rentals

Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7)
$271 nightly
The price is $287
Jan 29 - Jan 30, 2026
Total with taxes and fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
$331 nightly
The price is $350
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
Downtown Cambridge
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
$335 nightly
The price is $355
Jan 5 - Jan 6, 2026
Total with taxes and fees
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Interior
Upscale Condo in Annapolis

Upscale Condo in Annapolis

Upscale Condo in Annapolis
Historic District
10.0 out of 10, Exceptional, (2)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$529 nightly
The price is $603
Jan 5 - Jan 6, 2026
Total with taxes and fees
Upscale Condo in Annapolis
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very Good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
$263 nightly
The price is $279
Jan 12 - Jan 13, 2026
Total with taxes and fees
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$637 nightly
The price is $726
Jan 5 - Jan 6, 2026
Total with taxes and fees
Historic Row Home in Downtown Annapolis
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Room was spotless and all employees were very helpful and friendly."
Denise 1-night trip
Posted 20 hours ago
Graduate by Hilton Annapolis

Find out more about St. Michaels

St. Michaels Condo Rentals information

Number of reviews
32
Accommodation
14 Condo Rentals
Lowest Price
$279
Highest Price
$726

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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