Search Romantic Hotels in St. Michaels

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Check availability on St. Michaels Romantic Hotels

Our top choices for St. Michaels romantic hotels

Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is Rp7.834.385
Rp9.479.640 total
includes taxes & fees
14 Dec - 15 Dec
Inn at Perry Cabin
Reception
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
"Great place!"
United States
Tawnya
The price is Rp1.271.712
Rp1.449.752 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is Rp2.391.764
Rp3.250.809 total
includes taxes & fees
14 Dec - 15 Dec
Kent Island Resort
Outdoor wedding area
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is Rp1.773.242
Rp2.301.819 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
Lobby
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Great value for stay with breakfast included "
United States
Aisling
The price is Rp1.320.739
Rp1.505.644 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis Downtown
Meeting facility
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Meeting facility
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (841)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is Rp2.985.004
Rp3.283.504 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1000)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is Rp2.017.796
Rp2.300.287 total
includes taxes & fees
29 Dec - 30 Dec
Crowne Plaza Annapolis by IHG
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is Rp2.154.539
Rp2.456.174 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1002)
"Very courteous staff."
United States
Joseph
The price is Rp2.868.272
Rp3.705.740 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Regency Chesapeake Bay
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.
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Top St. Michaels Hotel Reviews

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Frequently asked questions

Searching for romantic hotels in St. Michaels?
Are you and your partner in need of a romantic getaway? Our guests also enjoy St. Michaels for its historic landmarks, shopping and seafood restaurants. If you want to explore the area, you might head to St. Michaels Marina, Chesapeake Bay Maritime Museum or St. Michaels Winery. If you're interested in staying near a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to St. Michaels?
If you're looking forward to lots of outings with your partner, take a look at these details about year-round temperatures in St. Michaels: The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for St. Michaels is 1341 mm.
What is there to do in St. Michaels?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all that St. Michaels has to offer. Couples looking for a little of everything will enjoy St. Michaels for its historic landmarks, shopping and seafood restaurants. You might think about visiting St. Michaels Marina, Chesapeake Bay Maritime Museum or St. Michaels Winery.
What's the best way to get to St. Michaels and around town during my romantic getaway?
These transportation options in St. Michaels might help your romantic trip get off to a smooth start: To get to St. Michaels, book a flight to Easton, MD (ESN-Easton - Newnam), which is the closest major airport, located 8.8 mi (14.1 km) from the city centre. If you'd like to explore around the area, you may want a rental car for your journey.