Photo by Meg Faller

Find Historic Hotels in Southern Maryland, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southern Maryland Historic Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top Southern Maryland Historic Hotels

Beach nearby, sun loungers, beach towels
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach
10.0 out of 10, Exceptional, (31)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is SAR 369
SAR 1,538 total
includes taxes & fees
9 Dec - 10 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Exterior
Hampton Inn Washington, D.C./White House

Hampton Inn Washington, D.C./White House

2.5 star property
Downtown Washington D.C.
9.0 out of 10, Wonderful, (1006)
"Easy check in"
United States
Philip
The price is SAR 302
SAR 350 total
includes taxes & fees
22 Dec - 23 Dec
Hampton Inn Washington, D.C./White House
Exterior
Capital Hilton

Capital Hilton

4.0 star property
Downtown Washington D.C.
8.6 out of 10, Excellent, (1005)
"Courteous staff and spacious clean rooms"
United States
Jennifer
The price is SAR 402
SAR 596 total
includes taxes & fees
19 Dec - 20 Dec
Capital Hilton
Premium bedding, down comforters, pillowtop beds, in-room safe
Le Meridien Washington, D.C., The Madison

Le Meridien Washington, D.C., The Madison

4.5 star property
Downtown Washington D.C.
9.2 out of 10, Wonderful, (1509)
"The staff and hotel are always top notch. My family and I had a great stay."
United States
PAUL E
The price is SAR 288
SAR 465 total
includes taxes & fees
21 Dec - 22 Dec
Le Meridien Washington, D.C., The Madison
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is SAR 507
SAR 722 total
includes taxes & fees
1 Jan - 2 January 2026
Wylder Tilghman Island
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1905)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (30)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel
Front of property
Flag House Inn

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (83)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
The price is SAR 686
SAR 782 total
includes taxes & fees
9 Dec - 10 Dec
Flag House Inn
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
The price is SAR 447
SAR 1,168 total
includes taxes & fees
9 Dec - 10 Dec
Cozy 2br home w/ parking in downtown Annapolis
3 bedrooms, iron/ironing board, travel crib, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★

★ Midcentury Modern Getaway ★ Prime Location ★

Historic District
10.0 out of 10, Exceptional, (35)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
United States
shannon r.
The price is SAR 1,043
SAR 2,580 total
includes taxes & fees
7 Jan - 8 January 2026
★ Midcentury Modern Getaway ★ Prime Location ★
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.
View all properties

Top Southern Maryland Hotel Reviews

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

10/10 Excellent
"Clean, updated , large room. Decorated beautifully for holiday"
Susan 1-night trip
Posted 4 days ago
Gaylord National Resort & Convention Center

Explore a world of travel with Expedia