Search for Cheap Deals on
Hotels in St. Michaels

Check Last Minute St. Michaels Hotel Deals

Tonight Jan 17 - Jan 18Next weekend Jan 23 - Jan 25

Choose from 1258 St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
  • 19 min walk from St. Michaels Winery
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
Good value and close to downtown.

Reviewed on Dec 31, 2025

St Michaels Inn
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
  • 10 min walk from St. Michaels Winery
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.6/10 Exceptional! (414 reviews)
The room was very clean. The staff was very pleasant and extremely helpful when we needed something @3:30am.

Reviewed on Jan 14, 2026

The Wildset
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
  • 13 min walk from St. Michaels Winery
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (373 reviews)
We had a great stay, hotel was very clean and food was great

Reviewed on Jan 3, 2026

Inn at Perry Cabin
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street St. Michaels MD
  • 12 min walk from St. Michaels Winery
Stay at this B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are ...
9.2/10 Wonderful! (130 reviews)
What a great stay! Beautiful B&B in St Michael’s! Our hosts Connie and Edward were very welcoming. Had great suggestions for dining and tourist attractions within the town. Our room was clean, comfortable and was perfect for our stay. The Inn also offers bikes to explore the area as well. Each afternoon, ...

Reviewed on Aug 11, 2025

Parsonage Inn
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
  • 39 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,000 reviews)
Clean and we moved to a quiet room as well

Reviewed on Jan 8, 2026

DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
  • 37 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.2/10 Wonderful! (1,007 reviews)
Beautiful hotel, easy walk to the pier/boat show.

Reviewed on Jan 15, 2026

Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
  • 37 min drive from St. Michaels Winery
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,894 reviews)
Clean room, staff was very friendly and kept in touch throughout stay, to see if I needed anything. Highly recommended staying here

Reviewed on Jan 12, 2026

Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
  • 36 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (897 reviews)
Very welcoming and room very clean.

Reviewed on Jan 4, 2026

Annapolis Waterfront Hotel, Autograph Collection
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
  • 40 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,001 reviews)
Easy

Reviewed on Jan 4, 2026

Crowne Plaza Annapolis by IHG
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
  • 40 min drive from St. Michaels Winery
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,005 reviews)
Great rooms, amenities, staff

Reviewed on Dec 29, 2025

Hyatt Regency Chesapeake Bay
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
  • 37 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.4/10 Very Good! (1,013 reviews)
We did not eat breakfast at the hotel-it was not included. I only tried to get coffee once and it was full of grounds. Most hotels have coffee and water out all day but there wasn't any available in the lobby in the afternoon or evening.

Reviewed on Jan 9, 2026

Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
  • 40 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,001 reviews)
Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future.

Reviewed on Jan 13, 2026

Country Inn & Suites by Radisson, Annapolis, MD
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.

Find cheap hotels in St. Michaels

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your St. Michaels hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in St. Michaels.

Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of St. Michaels’s 1,258 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $85. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great St. Michaels hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in St. Michaels. No matter your reason for visiting St. Michaels, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About St. Michaels hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in St. Michaels for as low as $85.

How many hotels are there in St. Michaels?

With over 1,258 hotels in St. Michaels, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $85.

How to find cheap car rentals in St. Michaels?

Finding a cheap car rental deal in St. Michaels is as easy as scoring cheap hotels in St. Michaels. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.