Search for Cheap Deals on
Hotels in St. Michaels

Check Last Minute St. Michaels Hotel Deals

Tonight Feb 21 - Feb 22This weekend Feb 21 - Feb 23

Choose from 1223 St. Michaels Hotel Deals

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
The price is $403 per night from Feb 23 to Feb 24
$403
includes taxes & fees
Feb 23 - Feb 24
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! (331 reviews)
"The property is beautiful and, the atmosphere is relaxing. I loved the fresh floral Christmas decorations."

Reviewed on Dec 30, 2024

Inn at Perry Cabin
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
The price is $94 per night from Mar 16 to Mar 17
$94
includes taxes & fees
Mar 16 - Mar 17
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! (1,001 reviews)
Perfect little getaway for great price
"Great location, staff was so nice, friendly and accommodating! The room was clean, bathroom could use some updating and bed was really firm so be prepared. Pillow top would definitely be beneficial. Great morning coffee, and continental breakfast was ok. Loved that they provide bottle waters. I would ..."

Reviewed on Feb 17, 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
The price is $241 per night from Feb 23 to Feb 24
$241
includes taxes & fees
Feb 23 - Feb 24
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! (297 reviews)
"Beautifully appointed with fireplace, big tub, deck & firepit. Would definitely come back!"

Reviewed on Feb 11, 2025

The Wildset
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
  • 37 min drive from St. Michaels Winery
The price is $173 per night from Mar 16 to Mar 17
$173
includes taxes & fees
Mar 16 - Mar 17
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,000 reviews)
"Great hotel! Very clean room and common areas. The staff was extremely friendly and accommodating and the location was perfect! Easily walkable to restaurant, bars, shopping and morning coffee!"

Reviewed on Feb 17, 2025

Graduate by Hilton Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
  • 37 min drive from St. Michaels Winery
The price is $193 per night from Feb 22 to Feb 23
$193
includes taxes & fees
Feb 22 - Feb 23
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
"Staff is friendly and helpful The WiFi isn’t working real well"

Reviewed on Feb 9, 2025

The Westin 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
The price is $198 per night from Mar 2 to Mar 3
$198
includes taxes & fees
Mar 2 - Mar 3
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 ...
8.8/10 Excellent! (1,727 reviews)
"Great location in Annapolis right in the center of everything. I did not realize that this hotel is actually 3 separate buildings some distance apart in the downtown. But they helped us to get to the building we were in. Parking with the hotel was $40 which was an unexpected additional expense."

Reviewed on Feb 19, 2025

Historic Inns of Annapolis
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
The price is $99 per night from Feb 25 to Feb 26
$99
includes taxes & fees
Feb 25 - Feb 26
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 ...
8.4/10 Very Good! (1,000 reviews)
"We had a great stay. We were very close to everything."

Reviewed on Feb 17, 2025

DoubleTree by Hilton Hotel Annapolis
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
  • 40 min drive from St. Michaels Winery
The price is $253 per night from Mar 15 to Mar 16
$253
includes taxes & fees
Mar 15 - Mar 16
Stay at this 4-star 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! (1,001 reviews)
Romantic get away
"Love staying here. The hot tub is great, love the common areas."

Reviewed on Feb 17, 2025

Hyatt Regency Chesapeake Bay
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
The price is $245 per night from Mar 16 to Mar 17
$245
includes taxes & fees
Mar 16 - Mar 17
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff ...
8.8/10 Excellent! (797 reviews)
"Staff was very friendly"

Reviewed on Feb 18, 2025

Annapolis Waterfront Hotel, Autograph Collection
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
The price is $99 per night from Mar 6 to Mar 7
$99
includes taxes & fees
Mar 6 - Mar 7
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,000 reviews)
"Great location, nice room! Clean, we will be back!"

Reviewed on Feb 16, 2025

Hilton Garden Inn Annapolis Downtown
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
  • 38 min drive from St. Michaels Winery
The price is $117 per night from Feb 28 to Mar 1
$117
includes taxes & fees
Feb 28 - Mar 1
Book a stay at this business-friendly hotel in Edgewater. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (763 reviews)
"Doriel was the quintessential hostess making me feel like I was so welcome! She was friendly, answered my questions and was more than willing to accommodate my needs. I highly recommend this location!"

Reviewed on Feb 19, 2025

Sonesta ES Suites Annapolis
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
  • 38 min drive from St. Michaels Winery
The price is $112 per night from Mar 23 to Mar 24
$112
includes taxes & fees
Mar 23 - Mar 24
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9/10 Wonderful! (1,000 reviews)
"My stay is wonderful as of now. The only issue was the sofa bed did not work. Staff came to set it up but stayed it was broken. We were given the option to change room but I chose not to."

Reviewed on Feb 17, 2025

SpringHill Suites by Marriott Annapolis
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 1,223 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 $94. 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 $94.

How many hotels are there in St. Michaels?

With over 1,223 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 $94.

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.