Find Historic Hotels in Southern Maryland, MD

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Check availability on Southern Maryland Historic Hotels

Top Southern Maryland Historic Hotels

MOUNT VERNON RETREAT 🌸
Outdoor dining

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (124)
"It whas the whole time a good time in this accomodation. The hosts were very friendly and it was a pleasant stay there."
MOUNT VERNON RETREAT 🌸
Wylder Tilghman Island
Waterfront Suite | Living area | 35-inch flat-screen TV with satellite channels

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (40)
"Always love staying here. This was my third visit. "
The price is AED 628
AED 838 total
includes taxes & fees
1 Jul - 2 Jul
Wylder Tilghman Island
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (27)
"Great trip with our family. We had the best time. Thank you !!!"
The price is AED 1,014
AED 2,563 total
includes taxes & fees
24 Jun - 25 Jun
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is AED 3,121
AED 5,115 total
includes taxes & fees
22 Jun - 23 Jun
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
On the beach, sun loungers, beach towels

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 AED 3,121
AED 5,049 total
includes taxes & fees
22 Jun - 23 Jun
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Freshly renovated 3-story home 1 block from USNA!
Fridge, microwave, oven, stovetop

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (34)
"It was a great place to stay- location, layout and everything else was perfect. Would stay again for sure! "
The price is AED 907
AED 2,876 total
includes taxes & fees
30 Jun - 1 Jul
Freshly renovated 3-story home 1 block from USNA!
★ Midcentury Modern Getaway ★ Prime Location ★
3 bedrooms, iron/ironing board, travel crib, WiFi

★ Midcentury Modern Getaway ★ Prime Location ★

10.0 out of 10, Exceptional, (33)
"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. "
The price is AED 1,015
AED 2,517 total
includes taxes & fees
2 Jul - 3 Jul
★ Midcentury Modern Getaway ★ Prime Location ★
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1782)
"Nice historic hotel close to Main Street. "
Historic Inns of Annapolis
86 State Circle - Luxury Boutique Hotel
Exterior

86 State Circle - Luxury Boutique Hotel

2.0 star property
The price is AED 850
AED 969 total
includes taxes & fees
25 Jun - 26 Jun
86 State Circle - Luxury Boutique Hotel
Cozy 2br home w/ parking in downtown Annapolis
Outdoor dining

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (69)
"Comfortable, clean home. Convenient walking distance to historic downtown Annapolis. "
The price is AED 1,017
AED 1,888 total
includes taxes & fees
16 Jul - 17 Jul
Cozy 2br home w/ parking in downtown Annapolis
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.