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Hotels in St. Michaels

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Choose from 1235 St. Michaels Hotel Deals

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 $114 per night from May 26 to May 27
$114
per night
May 26 - May 27
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! (1,003 reviews)
"Beautiful and convenient suite. Very helpful staff. Thank you!"

Reviewed on May 9, 2024

DoubleTree by Hilton Hotel Annapolis
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 $127 per night from May 14 to May 15
$127
per night
May 14 - May 15
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,000 reviews)
"This motel-like property is the best value in St. Michaels. It is adequate but not more. Their breakfast is extremely limited."

Reviewed on May 6, 2024

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 $279 per night from May 14 to May 15
$279
per night
May 14 - May 15
Stay at this hotel in St. Michaels. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the restaurant and the helpful staff in our reviews. ...
9.6/10 Exceptional! (228 reviews)
"Absolutely beautiful, clean, friendly staff and delicious food"

Reviewed on May 6, 2024

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
The price is $665 per night from May 20 to May 21
$665
per night
May 20 - May 21
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Popular attractions Chesapeake Bay Maritime Museum ...
9.4/10 Exceptional! (293 reviews)
Great one day, much needed getaway
"This property is beautiful. The staff were attentive and friendly. Only one night, and worth the money (to me). I love the quaint feel of the property, eventhough it is quite the opposite. Only had the grilled oysters...yum, as I wanted to eat off site and prople watch :-). Highly recommend staying ..."

Reviewed on Apr 30, 2024

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
The price is $230 per night from May 15 to May 16
$230
per night
May 15 - May 16
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesapeake Bay Maritime Museum and St. Michaels ...
9/10 Wonderful! (119 reviews)
"The owners were great hosts"

Reviewed on Apr 21, 2024

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 $270 per night from May 14 to May 15
$270
per night
May 14 - May 15
Stay at this 3-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chesapeake Bay Maritime Museum and St. Michaels ...
8.4/10 Very Good! (50 reviews)
"We loved that the historic house was built by the son of freedenslaved African Americans."

Reviewed on Dec 26, 2023

George Brooks House B&B
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 $161 per night from May 28 to May 29
$161
per night
May 28 - May 29
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! (1,611 reviews)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too ..."

Reviewed on May 9, 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
  • 37 min drive from St. Michaels Winery
The price is $195 per night from May 27 to May 28
$195
per night
May 27 - May 28
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 restaurant ...
9.2/10 Wonderful! (1,054 reviews)
"Quiet, clean, lovely!"

Reviewed on May 3, 2024

Graduate Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Crowne Plaza Annapolis, an IHG Hotel
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
  • 40 min drive from St. Michaels Winery
The price is $144 per night from May 19 to May 20
$144
per night
May 19 - May 20
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! (1,002 reviews)
"Parking limited on weekend evenings"

Reviewed on Apr 28, 2024

Crowne Plaza Annapolis, an IHG Hotel
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 $179 per night from May 22 to May 23
$179
per night
May 22 - May 23
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)
"Check in was easy and I got a free upgrade, with premium parking included. Most everything is great. My only complaint is slow service in the bar area for food."

Reviewed on May 8, 2024

Hyatt Regency Chesapeake Bay
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 $169 per night from May 19 to May 20
$169
per night
May 19 - May 20
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 and the clean ...
8.6/10 Excellent! (1,001 reviews)
"The property is okay. We found the beds to be extremely soft. The dining room in the lobby was not "welcoming" so we went elsewhere. We never received a receipt or text from the valet. The parking to be expensive. Also, the internet was not included in the cost of the room. I cannot remember the ..."

Reviewed on May 1, 2024

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 $247 per night from May 27 to May 28
$247
per night
May 27 - May 28
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! (710 reviews)
"I like everything about this property!"

Reviewed on May 10, 2024

Annapolis Waterfront Hotel, Autograph Collection
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in St. Michaels

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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 1,235 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 $46. 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 up to 60% 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 save up to 60% off 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 $46.

How many hotels are there in St. Michaels?

With over 1,235 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 $46.

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 even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to St. Michaels now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to St. Michaels right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.