Title: St. Michaels Condo Rentals from CA $374 | Expedia.ca [Hotels in St. Michaels](https://expedia.ca/St-Michaels-Hotels.d5940.Travel-Guide-Hotels)[Vacation Rentals in St. Michaels](https://expedia.ca/St-Michaels-Vacation-Rentals.d5940.Travel-Guide-VacationRentals)[Flights to St. Michaels](https://expedia.ca/Cheap-Flights-To-St-Michaels.d5940.Travel-Guide-Flights)[St. Michaels Car Rentals](https://expedia.ca/Car-Rentals-In-St-Michaels.d5940.Car-Rental-Guide)[St. Michaels Vacation Packages](https://expedia.ca/St-Michaels.d5940.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/e708a2ddef7b36b18845a12b959447e3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in St. Michaels from CA $374 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=5940&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=CONDO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select St. Michaels Condo Rentals ![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/6cf2c348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/0ab02fd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/17fb0bdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119330000/119327700/119327681/f2aff50d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront condo. Completely renovated. Walk to Kent Island's best places Chester [](https://www.expedia.ca/Chester-Hotels-Waterfront-Condo-Completely-Renovated-Walk-To-Kent-Islands-Best-Places.h119327681.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/a6910ef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/904b1187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/8f771580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player, stereo](https://images.trvl-media.com/lodging/33000000/32410000/32401200/32401110/1d4c3b60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Condominium in the heart of the historic center Historic District 9.8/10 Exceptional (284) "The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. " [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Condominium-In-The-Heart-Of-The-Historic-Center.h32401110.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/61e8c463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/2793baeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/868b127d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119340000/119331500/119331473/a4a8578b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station House East: Upscale Loft in the Historic District Cambridge, MD Downtown Cambridge CA $100 CA $373 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Cambridge-Hotels-Station-House-East-Upscale-Loft-In-The-Historic-District-Cambridge.h119331473.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/3d98a748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/a6db755d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/876912bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/d953bc28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Downtown Annapolis Condo With Free Parking Historic District 10/10 Exceptional (30) "Clean, modern apartment walking distance from all of Annapolis harbor and restaurants. " CA $206 CA $513 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Annapolis-Hotels-Downtown-Annapolis-Condo-W-Free-Parking-Coffee.h69666468.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33500000/33496000/33495970/w4000h2785x0y0-a6314b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/34000000/33500000/33496000/33495970/de8cbbab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33500000/33496000/33495970/0380a45e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/34000000/33500000/33496000/33495970/fbaa80f0_edited_5099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Condo - Water View Near City Dock Eastport 9.6/10 Exceptional (147) "Clean, quiet, and very close to both downtown and Eastport restaurants." [](https://www.expedia.ca/Annapolis-Hotels-Beautiful-Condo-Water-View-Near-City-Dock.h33495970.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/e8133ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/dea9ce41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/e11d1711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103590000/103584900/103584811/70d83c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland Downtown Cambridge 8.8/10 Excellent (5) "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!" CA $173 CA $414 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Cambridge-Hotels-Upscale-Condo-In-Historic-Downtown-Cambridge.h103584811.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/5d73c26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/1d7053f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/9efcf95e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/107000000/106750000/106747700/106747609/e6213ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge Downtown Cambridge 9.8/10 Exceptional (9) "This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. " CA $214 CA $497 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Cambridge-Hotels-The-Drinking-Gourd-Stunning-Penthouse-In-Historic-Downtown-Cambridge.h106747609.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/92000000/91720000/91716400/91716310/5e4afe63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/92000000/91720000/91716400/91716310/2c7dd938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91720000/91716400/91716310/5be6520b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91720000/91716400/91716310/359e5281.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking Eastport 10/10 Exceptional (20) "Can’t have a better location near everything in Eastport and Main St Annapolis!" [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-Condo-With-Rooftop-Pool.h91716310.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/104000000/103120000/103118000/103117987/32ee74d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103120000/103118000/103117987/79e9e91c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/104000000/103120000/103118000/103117987/8d80ad00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103120000/103118000/103117987/f0a7fcb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront 2-Bedroom Condo on Spa Creek Eastport 10/10 Exceptional (9) "This is a great location. Walking distance to everything. Near all the sailing clubs! Property manager was the best we have ever experienced." [](https://www.expedia.ca/Annapolis-Hotels-Waterfront-2-Bedroom-Condo-On-Spa-Creek.h103117987.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/8ef85715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/7203703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/w906h683x59y0-0dacccf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/84000000/83760000/83759400/83759327/c9b4e203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Waterfront Cottage Stevensville 8.8/10 Excellent (11) "Enjoyed fishing at the pier and sitting on the porch" [](https://www.expedia.ca/Stevensville-Hotels-Chester-River-Waterfront-Cottage.h83759327.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/65fc84d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/faf796a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/d22532b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/106000000/105950000/105946100/105946058/ee3b6008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland Downtown Cambridge 10/10 Exceptional (10) "Just a beautiful place. I would stay here again. Everything was walking distance. " CA $242 CA $530 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Cambridge-Hotels-Conductors-Rest-Beautiful-2-Bedroom-Loft-In-Historic-Cambridge.h105946058.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/108000000/107220000/107214300/107214209/c652a2ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107220000/107214300/107214209/90568bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/108000000/107220000/107214300/107214209/c7b44c49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107220000/107214300/107214209/dfbe56e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Unbelievable beach views for 6 North Beach 10/10 Exceptional (9) "It was unbelievable stay with fantastic sunrise and moon rise on the day of the eclipse" [](https://www.expedia.ca/North-Beach-Hotels-Unbelievable-Beach-Views-For-6.h107214209.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/58000000/57560000/57550300/57550236/4508070a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57560000/57550300/57550236/2d0419b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/58000000/57560000/57550300/57550236/edb417dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57560000/57550300/57550236/7d7c4780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Condo w/ Balcony in the Heart of Annapolis! Historic District 9.8/10 Exceptional (59) "This cute condo is as pictured; charming and clean. Nice bathrooms. Comfortable beds. Great location. Loved the parking ease as well. Host was very receptive and flexible with my arrival/departure times.Would highly recommend and would stay here again." [](https://www.expedia.ca/Annapolis-Hotels-Chic-Condo-W-Balcony-In-The-Heart-Of-Annapolis.h57550236.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503736/cf444309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503736/01597921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503736/d6216185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/120000000/119510000/119503800/119503736/ec8e0e59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 3 Bedroom/2.5 bathroom close to Naval Academy, NMCM Stadium, and downtown. Annapolis [](https://www.expedia.ca/Annapolis-Hotels-3-Bedroom25-Bathroom-Close-To-Naval-Academy.h119503736.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-08&endDate=2025-10-09®ionId=5940&adults=2&lodging=CONDO&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSt-Michaels-Condos.d5940-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSt-Michaels-Condos.d5940-aaCondos.Travel-Guide-Accommodation) ## Top St. Michaels Hotel Reviews ![The Wildset](//images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg) ### The Wildset 10/10 Excellent "Lovely and spacious updated room. Very clean and comfortable. Could use curtains to block some of the light getting in through the slat blinds. Otherwise a great hotel with a perfect location. Would definitely recommend. " [](https://expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![Courtyard by Marriott Annapolis](//images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "Extremely cozy. Felt good to just relax." [](https://expedia.ca/Annapolis-Hotels-Courtyard-By-Marriott-Annapolis.h11049.Hotel-Information) ![John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!](//images.trvl-media.com/lodging/33000000/32570000/32562400/32562385/c5bdec51_y.jpg) ### John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels! 10/10 Excellent "Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!" [](https://expedia.ca/St-Michaels-Hotels-John-Bruff-Waterview-Cottage-On-Harbor-And-On-Park-In-Town-St-Michaels.h32562385.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "My wife and were away to celebrate our 34th wedding anniversary and the stay was close to home affordable and very comfortable. Hotel staff was very friendly and welcoming " [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "No additional comment. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "I was perfect for our visit. Close to everything." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Stayed for one night; room was nice, easy to access, and located near numerous local attractions. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hyatt Regency Chesapeake Bay](//images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg) ### Hyatt Regency Chesapeake Bay 10/10 Excellent "Beautiful place" [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) ## Find out more about St. Michaels ## St. Michaels Condo Rentals information | Number of reviews | 501 | | --- | --- | | Accommodation | 17 Condo Rentals | | Lowest Price | CA $374 | | Highest Price | CA $530 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Eastern Shore](https://www.expedia.ca/4Star-Eastern-Shore-Hotels.s40-0-d6025644.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Eastern Shore](https://www.expedia.ca/5Star-Eastern-Shore-Hotels.s50-0-d6025644.Travel-Guide-Filter-Hotels) - [Hotels near Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) - 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