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Name: Hilton Garden Inn Annapolis Downtown
Price range: $96 total

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Cheap St. Michaels Hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$574 nightly

$632 total

Dec 18 - Dec 19

Total with taxes and fees

0.29 mi from city center

A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.

Pool

Hot Tub

St Michaels Inn

1228 S Talbot Street St. Michaels MD

$101 nightly

$111 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

Free Cancellation

1.53 mi from city center

When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime Museum.

Pool

Breakfast included

The Wildset

209 N Talbot St St. Michaels MD

$209 nightly

$230 total

Dec 18 - Dec 19

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

0.09 mi from city center

With a stay at The Wildset in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town Hall.

Breakfast included

Pet friendly

George Brooks House B&B

24500 Rolles Range Road St. Michaels MD

$170 nightly

$187 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

0.77 mi from city center

When you stay at George Brooks House B&B in St. Michaels, you'll be within a 5-minute drive of Chesapeake Bay Maritime Museum.

Pool

Breakfast included

Parsonage Inn

210 North Talbot Street St. Michaels MD

$200 nightly

$220 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

0.21 mi from city center

With a stay at Parsonage Inn in St. Michaels (Downtown St. Michaels), you'll be within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Winery.

Breakfast included

Pet friendly

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD

0.12 mi from city center

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD

0.11 mi from city center

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Historic Inns of Annapolis

58 State Circle Annapolis MD

$164 nightly

$187 total

Dec 23 - Dec 24

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

19.51 mi from city center

With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.

Pet friendly

Free WiFi

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$80 nightly

$92 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

21.92 mi from city center

With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta Kinte Alex Haley Memorial.

Pet friendly

Parking included

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

$178 nightly

$203 total

Dec 23 - Dec 24

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

19.21 mi from city center

With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and William Paca House.

Pet friendly

Free WiFi

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$105 nightly

$120 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

Free Cancellation

22.03 mi from city center

Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical Center.

Pool

Parking included

Hilton Garden Inn Annapolis Downtown

174 West Street Annapolis MD

$85 nightly

$96 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

19.84 mi from city center

With a stay at Hilton Garden Inn Annapolis Downtown, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.

Pet friendly

Free WiFi

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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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St. Michaels hotels essential information

Accommodation	1,251 hotels
Lowest Price	$92
Highest Price	$632
Popular hotels	Inn at Perry Cabin, St Michaels Inn, The Wildset, George Brooks House B&B, Parsonage Inn, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Crowne Plaza Annapolis by IHG, Hilton Garden Inn Annapolis Downtown