Search for Cheap Deals on
Hotels in St. Michaels

Choose from 1257 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 $554 per night from Apr 17 to Apr 18
$554
includes taxes & fees
Apr 17 - Apr 18
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! (340 reviews)
"Our stay here was excellent. The highlight was arguably the check-in, where we were surprised with a birthday welcome, as well as a little onesie for our soon to arrive baby girl. This was a birthday/baby moon trip and we shared this info prior to arrival, and the staff was incredible in providing ..."

Reviewed on Apr 5, 2025

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 $136 per night from Apr 17 to Apr 18
$136
includes taxes & fees
Apr 17 - Apr 18
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! (1,002 reviews)
"Just a Great exceptionally clean facility! Super simple check in and extremely comfortable and the Cost is absolutely fantastic over the chains !"

Reviewed on Apr 11, 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 $263 per night from Apr 21 to Apr 22
$263
includes taxes & fees
Apr 21 - Apr 22
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! (307 reviews)
"Property was clean and the staff was very nice. Location is perfect to do everything you may want to do. Only thing I would say is there is no microwave on property that we saw to reheat food and no chairs in the room, just the bed and a bench."

Reviewed on Apr 14, 2025

The Wildset
Parsonage Inn
Parsonage Inn
3.5 out of 5
210 North Talbot Street, St. Michaels, MD
  • 12 min walk from St. Michaels Winery
The price is $231 per night from Apr 21 to Apr 22
$231
includes taxes & fees
Apr 21 - Apr 22
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and ...
9/10 Wonderful! (127 reviews)
"exceptional hosts: above and beyond for service, suggestions, accommodation, effort to assist . impressive found by accident, would reccommend and visit AGAIN"

Reviewed on Mar 17, 2025

Parsonage Inn
George Brooks House B&B
George Brooks House B&B
3 out of 5
24500 Rolles Range Road, St. Michaels, MD
  • 22 min walk from St. Michaels Winery
The price is $198 per night from Apr 17 to Apr 18
$198
includes taxes & fees
Apr 17 - Apr 18
Stay at this 3-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Chesapeake Bay Maritime ...
8.6/10 Excellent! (57 reviews)
"Very nice property, cozy and clean rooms, excellent service."

Reviewed on Sep 15, 2024

George Brooks House B&B
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
The price is $106 per night from Apr 28 to Apr 29
$106
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,007 reviews)
"Happy with our stay here. Convenient to downtown. Would stay again"

Reviewed on Apr 11, 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 $199 per night from Apr 22 to Apr 23
$199
includes taxes & fees
Apr 22 - Apr 23
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! (1,732 reviews)
"Charming to stay in a historic property so close to the State House and an easy walk to the City Dock"

Reviewed on Apr 14, 2025

Historic Inns of 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 $170 per night from Apr 20 to Apr 21
$170
includes taxes & fees
Apr 20 - Apr 21
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! (999 reviews)
"Stayed here for a wedding, but it was our first time to the area. Hotel is great, clean friendly. But the real value was the location. Walking distance to restaurants, convenience, stores, and bars. It was an eight minute walk to a super cute coffee shop, bakery. Parking seemed unnecessarily expensive, ..."

Reviewed on Apr 7, 2025

The Westin 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
The price is $227 per night from Apr 27 to Apr 28
$227
includes taxes & fees
Apr 27 - Apr 28
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (808 reviews)
"Good"

Reviewed on Mar 23, 2025

Annapolis Waterfront Hotel, Autograph Collection
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 $274 per night from May 6 to May 7
$274
includes taxes & fees
May 6 - May 7
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! (1,002 reviews)
"Great spot."

Reviewed on Apr 8, 2025

Hyatt Regency Chesapeake Bay
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
The price is $125 per night from Apr 21 to Apr 22
$125
includes taxes & fees
Apr 21 - Apr 22
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,002 reviews)
"It was fine"

Reviewed on Apr 12, 2025

Crowne Plaza Annapolis by IHG
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 $106 per night from Apr 20 to Apr 21
$106
includes taxes & fees
Apr 20 - Apr 21
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! (1,003 reviews)
"Hotel is close to everything, mall, food, shopping"

Reviewed on Mar 31, 2025

DoubleTree by Hilton Hotel 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 1,257 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 $106. 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 $106.

How many hotels are there in St. Michaels?

With over 1,257 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 $106.

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.