Search Condos Rentals in St. Michaels from CA $194

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select St. Michaels Condo Rentals

Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (22)
"Very nice location and nice apartment!"
Downtown Annapolis Condo w/ Free Parking + Coffee
Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (270)
"Great location. Clean and very roomy!"
Annapolis Condominium in the heart of the historic center
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Point of interest

Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking

10.0 out of 10, Exceptional, (16)
"Absolutely perfect. Wonderful location. Beautiful property. Great staff made the weekend easy. "
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Beautiful Condo - Water View Near City Dock
Outdoor dining

Beautiful Condo - Water View Near City Dock

9.6 out of 10, Exceptional, (144)
"We came up for the bowl game in Annapolis and this place offered a great place to stay near downtown and access to anywhere! The condo offered a clean comfortable place with all you need so close. "
Beautiful Condo - Water View Near City Dock
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
Pool

Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!

10.0 out of 10, Exceptional, (9)
"great stay and great communication short walk to everything"
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
Chic Condo w/ Balcony in the Heart of Annapolis!
Interior

Chic Condo w/ Balcony in the Heart of Annapolis!

9.8 out of 10, Exceptional, (54)
"We have stayed in this building 3 times, and the location and the set up of the units are excellent. The complex is safe, quiet and is in a great location. It also is very accessible for handicap and having a secure parking spot is advantageous. "
Chic Condo w/ Balcony in the Heart of Annapolis!
Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, free WiFi, bed sheets

Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is CA $194
CA $439 total
includes taxes & fees
May 4 - May 5
Upscale Condo in Historic Downtown Cambridge, Maryland
Water-view condo with rooftop pool & balcony - minutes from downtown
TV

Water-view condo with rooftop pool & balcony - minutes from downtown

9.2 out of 10, Wonderful, (9)
"We came for a few days of the Annapolis boat show. Loved the location. Bed is super comfortable and tv easy to watch. Couch comfy and place had everything we needed. Would stay again for sure"
Water-view condo with rooftop pool & balcony - minutes from downtown
Unbelievable beach views for 6
Property grounds

Unbelievable beach views for 6

2.0 star property
10.0 out of 10, Exceptional, (6)
"Very nice place in a great location!!!"
Unbelievable beach views for 6
Kent Island Waterfront Cottage
Beach

Kent Island Waterfront Cottage

9.4 out of 10, Exceptional, (8)
"Spent the weekend with the family here. Really great location and the place was very comfortable. Thoroughly enjoyed our stay."
Kent Island Waterfront Cottage
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Exterior

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

2.5 star property
10.0 out of 10, Exceptional, (8)
"The condo was very well appointed and super clean. Interior design was beautiful, we love the views from the second floor. Cambridge is a great town we enjoyed walks, beer at RAR and good food. We would definitely stay at this place again. "
The price is CA $270
CA $600 total
includes taxes & fees
May 5 - May 6
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Property grounds

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (7)
"The Drinking Gourd was clean, cozy and attractive. In spite of its central location, it was quiet. We would stay there again!"
The price is CA $291
CA $586 total
includes taxes & fees
May 27 - May 28
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Waterfront 2-Bedroom Condo on Spa Creek
Interior

Waterfront 2-Bedroom Condo on Spa Creek

10.0 out of 10, Exceptional, (8)
"We had such an amazing time. It had a beautiful view and easy to walk everywhere :)"
Waterfront 2-Bedroom Condo on Spa Creek
Delightful little Historic District gem - for the antique lover and history buff.
Fridge, microwave, oven, stovetop

Delightful little Historic District gem - for the antique lover and history buff.

9.0 out of 10, Wonderful, (4)
"Excellent location for all things USNA and downtown Annapolis. We walked everywhere. The second bedroom was a little warm but it was unseasonably hot while we were there. There is a K cup coffeemaker but you’ll need to bring everything to enjoy a cup. Would definitely stay again!"
Delightful little Historic District gem - for the antique lover and history buff.
A Kozy Waterfront Condo
Pool

A Kozy Waterfront Condo

A Kozy Waterfront Condo
Unique 2-Bedroom Condo in Renovated Church Parish House
Point of interest

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
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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Other property types in St. Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (118)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The heart of St Michaels awaits.
Exterior

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (35)
"We really enjoyed our stay. Accommodations were exactly as expected and advertised. Would certainly stay here again."
The heart of St Michaels awaits.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (35)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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.

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.