Search for Cheap Deals on
Hotels in St. Michaels

Choose from 1270 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)
"They tried in every way to make us comfortable ."

Reviewed on Nov 10, 2026

St Michaels Inn
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. ...
9.6/10 Exceptional! (407 reviews)
"Beautiful property but rooms in need of some updates. (Dirty carpets, moldy curtains). Beds very comfortable!For $1200 a night with no amenities, it was a disappointment but was a fun trip!"

Reviewed on Oct 18, 2026

Inn at Perry Cabin
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. ...
9.8/10 Exceptional! (528 reviews)
"They double booked my room and did not give me any options so was basically homeless"

Reviewed on Nov 8, 2026

The Wildset
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street St. Michaels MD
  • 10 min walk from St. Michaels Winery
Stay at this B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Higgins Yacht Yard and Marina and Muskrat Park are located ...
9.2/10 Wonderful! (139 reviews)
"The staff were great. The breakfast was delicious and the location is perfect for walking into town."

Reviewed on Nov 7, 2026

Parsonage Inn
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! (2,069 reviews)
"We liked the location of inn which was near Main St and the dock area"

Reviewed on Nov 9, 2026

Historic Inns of Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
  • 31 min drive from St. Michaels Winery
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,000 reviews)
"Beautiful place and had everything and more for the weekend we stayed."

Reviewed on Nov 9, 2026

Rod 'N' Reel Resort
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 ...
8.8/10 Excellent! (1,014 reviews)
"The hot tub was broken. But the staff was helpful, the rooms were big and clean"

Reviewed on Nov 10, 2026

Crowne Plaza Annapolis by IHG
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
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! (1,010 reviews)
"Parking fee $7/day. In walking distance, nice coffee and brunch place"

Reviewed on Nov 9, 2026

Sonesta ES Suites 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
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 ...
8.8/10 Excellent! (1,274 reviews)
"Property is dated and needs a facelift. Hallways smell a little dank and musty. Rooms were ok, but definitely could use updating ."

Reviewed on Nov 8, 2026

DoubleTree by Hilton Hotel 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! (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"

Reviewed on Nov 5, 2026

Annapolis Waterfront Hotel, Autograph Collection
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! (1,064 reviews)
"Staff professional and helpful, room and common areas well maintained. Hot breakfast provided. Parking easy and accessible."

Reviewed on Nov 9, 2026

Country Inn & Suites by Radisson, Annapolis, MD
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 ...
Graduate by Hilton 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 1,270 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 $92. 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 $92.

How many hotels are there in St. Michaels?

With over 1,270 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 $92.

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.