Historic Hotels & Resorts in Southern Maryland

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Check availability on Southern Maryland Historic Hotels

Tonight
5 Aug - 6 Aug
Tomorrow
6 Aug - 7 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Best Southern Maryland Historic Hotels

Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1824)
"Loved the hotel-great location "
Historic Inns of Annapolis
The Henley Park Hotel
Classic architecture meets serene gardens at The Heyley Park Hotel's elegant entrance.

The Henley Park Hotel

4.0 star property
9.0 out of 10, Wonderful, (1135)
"It was a really nice stay."
The price is AU$156
includes taxes & fees
10 Aug - 11 Aug
The Henley Park Hotel
Phoenix Park Hotel
Experience the classic charm of this urban hotel, offering a convenient location near the Capitol building.

Phoenix Park Hotel

3.5 star property
9.4 out of 10, Exceptional, (2231)
"Really wonderful stay, very close to Union Station, some museums and great dining options as well! "
Phoenix Park Hotel
MOUNT VERNON RETREAT 🌸
Relax in a serene outdoor setting with a table and two chairs, surrounded by lush greenery and potted plants.

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (125)
"This a great basement apartment. Large rooms, very clean and nice outdoor space. Good for family and nice safe neighborhood. "
The price is AU$393
includes taxes & fees
12 Aug - 13 Aug
MOUNT VERNON RETREAT 🌸
Morrison Clark Historic Inn
Step into a grand lobby with a soaring ceiling, ornate chandeliers, and a grand staircase.

Morrison Clark Historic Inn

4.0 star property
9.4 out of 10, Exceptional, (1831)
"Excellent accommodations and service. "
The price is AU$195
includes taxes & fees
11 Aug - 12 Aug
Morrison Clark Historic Inn
The Mayflower Hotel, Autograph Collection
Classic hotel with a symmetrical facade and central entrance, featuring a blend of traditional and modern architectural influences.

The Mayflower Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (1001)
"Friendly staff. Very nice hotel. Great location"
The price is AU$296
includes taxes & fees
8 Aug - 9 Aug
The Mayflower Hotel, Autograph Collection
The Churchill Hotel near Embassy Row
Experience the classic charm of the Churchill Hotel, featuring a symmetrical facade with numerous windows and decorative elements.

The Churchill Hotel near Embassy Row

4.0 star property
8.8 out of 10, Excellent, (1821)
"beautiful property comfortable breakfast was fantastic"
The Churchill Hotel near Embassy Row
Cozy 2br home w/ parking in downtown Annapolis
Enjoy waterfront views from the dock with a metal ladder and brick wall, surrounded by a serene grassy area with a bench and lamp post.

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"Comfortable, clean home. Convenient walking distance to historic downtown Annapolis. "
The price is AU$570
includes taxes & fees
25 Aug - 26 Aug
Cozy 2br home w/ parking in downtown Annapolis
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large window, and ample countertop space.

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

9.8 out of 10, Exceptional, (28)
"We loved the waterfront home where we stayed. The host was incredibly helpful and responsive to any questions we had about the rental and the area. Highly recommend."
The price is AU$1,007
includes taxes & fees
18 Aug - 19 Aug
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Ospreys perch on a scenic waterfront structure overlooking a serene body of water.

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

10.0 out of 10, Exceptional, (75)
"Property and Host were exceptional."
The price is AU$2,052
includes taxes & fees
11 Aug - 12 Aug
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
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.

Top Southern Maryland Hotel Reviews

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

10/10 Excellent
"The Gaylord is one of the most Epic Hotels I’ve ever stayed at!!! Treat yourself book a stay here. "
Sherri 3-night trip
Posted 1 day ago
Gaylord National Resort & Convention Center