Compare St. Michaels Condo Rentals

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Featured Condo Rentals in St. Michaels

Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock

Annapolis MD
This condo offers a water park, an outdoor pool, and laundry facilities.
Waterfront Suite with Views of Annapolis, Pool & Prime Eastport Location

Waterfront Suite with Views of Annapolis, Pool & Prime Eastport Location

Annapolis MD
This condo features an outdoor pool and laundry facilities.
Station House East: Upscale Loft in the Historic District Cambridge, MD

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

Cambridge MD
$227 nightly
The price is $240 total per night
$240 total
Dec 15 - Dec 16
Total with taxes and fees
At this condo, guests have access to features like laundry facilities.
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

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

Cambridge MD
$259 nightly
The price is $275 total per night
$275 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
At this condo, guests have access to features like laundry facilities and local meal delivery service.
Waterfront 2-Bedroom Condo on Spa Creek

Waterfront 2-Bedroom Condo on Spa Creek

Annapolis MD
At this condo, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free condo building also has a garden.
New Downtown Annapolis Condo With Free Parking

New Downtown Annapolis Condo With Free Parking

Annapolis MD
$320 nightly
The price is $365 total per night
$365 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of this condo enjoy features like a water park and laundry facilities.
Upscale Condo in Annapolis

Upscale Condo in Annapolis

Annapolis MD
$529 nightly
The price is $603 total per night
$603 total
Dec 22 - Dec 23
Total with taxes and fees
At this condo, guests have access to features like laundry facilities.
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2 out of 5
Cambridge MD
$316 nightly
The price is $335 total per night
$335 total
Dec 15 - Dec 16
Total with taxes and fees
At this condo, guests have access to features like laundry facilities and local meal delivery service.
Unbelievable beach views for 6

Unbelievable beach views for 6

2 out of 5
North Beach MD
At this condo, guests have access to features like laundry facilities.
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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.

Hotel Options in St. Michaels

    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln St. Michaels MD
    $574 nightly
    The price is $632 total per night from Dec 23 to Dec 24
    $632 total
    Dec 23 - Dec 24
    Total with taxes and fees
    9.4/10 Exceptional! (371 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street St. Michaels MD
    $105 nightly
    The price is $116 total per night from Dec 24 to Dec 25
    $116 total
    Dec 24 - Dec 25
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)
    The Wildset

    The Wildset

    209 N Talbot St St. Michaels MD
    $219 nightly
    The price is $241 total per night from Dec 15 to Dec 16
    $241 total
    Dec 15 - Dec 16
    Total with taxes and fees
    9.6/10 Exceptional! (408 reviews)

Luxury Condos

Find luxury condos in St. Michaels
Get your vacation off to a fabulous start by booking a luxury condo in St. Michaels. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a St. Michaels condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.  

Exploring St. Michaels will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

St. Michaels Condo Rentals essential information

Accommodation
14 Condo Rentals
Lowest Price
$116
Highest Price
$632
Popular accommodation
Beautiful Condo - Water View Near City Dock , Waterfront Suite with Views of Annapolis, Pool & Prime Eastport Location, Station House East: Upscale Loft in the Historic District Cambridge, MD, Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland, Waterfront 2-Bedroom Condo on Spa Creek, New Downtown Annapolis Condo With Free Parking, Upscale Condo in Annapolis, The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge, Unbelievable beach views for 6

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