Title: St. Michaels Vacation Packages & Trips 2025/2026 from CA $1,195 | 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) ![](https://images.trvl-media.com/place/5940/6d454cf3-0755-44c6-999f-dfbbe160658d.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # St. Michaels Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your St. Michaels Vacation The fascinating city of St. Michaels is calling your name. Immerse yourself in everything it has to offer with a St. Michaels vacation package that's tailored to you. You'll want to take in some sights during your trip to St. Michaels. Drop by major attractions such as [St. Michaels Winery](https://www.expedia.ca/St-Michaels-Winery-St-Michaels.d553248633992438808.Vacation-Attraction), [Chesapeake Bay Maritime Museum](https://www.expedia.ca/Chesapeake-Bay-Maritime-Museum-St-Michaels.d553248633992441010.Vacation-Attraction) and [St. Michaels Museum](https://www.expedia.ca/St-Michaels-Museum-St-Michaels.d553248621561196327.Vacation-Attraction). Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your St. Michaels vacation plans in motion! ## Top St. Michaels Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City CA $1,195 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 9/10 Wonderful! (3,258 reviews) Room was roomy and comfortable Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=YYZ&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=800771&paandie=true&dealMarker=IqvwG83huhhpNg9LbctiC_npZ3y4I35pQ3Q3BHcwmqjMPX6Cx1Fb1BOfoJuB3rCh) ![Miramar Condominiums](https://images.trvl-media.com/lodging/91000000/90310000/90308700/90308605/f837bfd4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miramar Condominiums Downtown Ocean City CA $1,904 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 9.4/10 Exceptional! (15 reviews) Stayed in unit 505 and it was beautiful! We loved it! Reviewed on Aug 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=YYZ&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=90308605&paandie=true&dealMarker=IqvwG83huhhpNg9LbctiC6dDROSOiy0gb4F19DGb71uNLitaEofxQmJcUBrfkAcU) ![Bay Club Resort by Coolvacay](https://images.trvl-media.com/lodging/46000000/45680000/45678500/45678471/e0329bbe_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Club Resort by Coolvacay Midtown Ocean City CA $1,329 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 8.4/10 Very Good! (39 reviews) I loved the dock and the gorgeous sunsets . Reviewed on Sep 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=YYZ&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=45678471&paandie=true&dealMarker=IqvwG83huhhpNg9LbctiC9HD4SV4MwfMi-LhNn9AhMzJKlx86oW1e9Y0-wqZkGXV) ![Atlantic Oceanside Dewey](https://images.trvl-media.com/lodging/17000000/16170000/16164500/16164449/fdd83f89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Atlantic Oceanside Dewey CA $2,357 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 8/10 Very Good! (971 reviews) We stayed last April, no real complaints. Our stay in November the room was a little rough. Floor and trim were very dirty. Tub filled with water when showering and the plumbing made a loud noise while shower was on. It’s still a decent place for the price but was a little disappointed in the cleanliness this time. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=YYZ&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=16164449&paandie=true&dealMarker=nRJDPqpFm59p2i4sqz1ZUr1DGADmqqZOUh5vjFfBRyaehj2OTbVYLz69f6C7zw3A) ![Hyatt Place Dewey Beach](https://images.trvl-media.com/lodging/7000000/6100000/6099400/6099301/9ad04713_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Dewey Beach CA $1,322 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 8.8/10 Excellent! (1,001 reviews) Excellent family and pet friendly hotel on the beach and walking distance to several other beaches, restaurants, and shops. Rooms were clean and updated, parking was easy, and complimentary breakfast was great. The indoor pool was also very clean and not too cold. Very happy with our experience here with our child and dogs. We would definitely stay here again! Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-26/2026-02-02/?FromAirport=YYZ&Destination=SBY&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6099301&paandie=true&dealMarker=IqvwG83huhhpNg9LbctiC9HD4SV4MwfMi-LhNn9AhMwBcsouvQcX5vd8tH-whSFx) ## Ready to book your vacation to St. Michaels? Choose your dates ## St. Michaels Hotel Deals ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### St Michaels Inn 1228 S Talbot Street, St. Michaels, MD Fully refundable CA $150 CA $166 total Nov 10 - Nov 11 includes taxes & fees 8/10 Very Good! (1,001 reviews) It was a clean room.The pricepoint was good.The heater was very noisy.The breakfast was nice. Good value for the price Reviewed on Nov 5, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=10281&PinnedHotelID=10281&HadPinnedHotel=true®ionId=5940) ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Inn at Perry Cabin 308 Watkins Ln, St. Michaels, MD CA $542 CA $656 total Nov 24 - Nov 25 includes taxes & fees 9.4/10 Exceptional! (368 reviews) Friendly and attentive staff, good cleaning services Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=14576&PinnedHotelID=14576&HadPinnedHotel=true®ionId=5940) ![The Wildset](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wildset 209 N Talbot St, St. Michaels, MD CA $308 CA $369 total Dec 7 - Dec 8 includes taxes & fees 9.6/10 Exceptional! (395 reviews) We loved the FRESH (and free) breakfast. The room was great. Liked the big shower and having our own entrance. The vibe/atmosphere at the Ruse was great. Good customer service/friendly staff. Reviewed on Oct 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=64410566&PinnedHotelID=64410566&HadPinnedHotel=true®ionId=5940) [See all 1,271 properties in St. Michaels](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F11%2F2025&endDate=11%2F11%2F2025®ionId=5940) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)