Find Winery Hotels in Southern Maryland, MD

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Top Southern Maryland Winery Hotels

Outdoor pool
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings
10.0 out of 10, Exceptional, (48)
"Lovely property."
United States
Melissa W.
The price is AED 433
AED 958 total
includes taxes & fees
20 Nov - 21 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
On the beach
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict
9.0 out of 10, Wonderful, (6)
"Sophia the host is super attentive and responsive"
United States
Mayela
The price is AED 661
AED 1,099 total
includes taxes & fees
14 Nov - 15 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
3 bedrooms, iron/ironing board, travel crib, free WiFi
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick
9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is AED 735
AED 1,441 total
includes taxes & fees
16 Nov - 17 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Interior
Peaceful Waterfront Apartment in the Heart of Solomons Island

Peaceful Waterfront Apartment in the Heart of Solomons Island

Solomons
9.0 out of 10, Wonderful, (14)
"Very clean, awesome location and amazing hosts!! "
United States
Jeff R.
The price is AED 496
AED 1,012 total
includes taxes & fees
14 Nov - 15 Nov
Peaceful Waterfront Apartment in the Heart of Solomons Island
Microwave, oven, stovetop, dishwasher
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons
9.6 out of 10, Exceptional, (7)
"The house was beautiful and well stocked with the necessities and even extras we didn’t expect. The service from the owner was great and always quick to respond to our questions. We are definitely looking forward to staying at this or another property next year! "
United States
Shewana S.
The price is AED 921
AED 1,992 total
includes taxes & fees
17 Nov - 18 Nov
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops
Beach
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick
10.0 out of 10, Exceptional, (8)
"This house was extremely clean and a comfortable choice for 4 older adults attending a family wedding in St Leonard. "
United States
Susan W.
The price is AED 797
AED 1,503 total
includes taxes & fees
17 Nov - 18 Nov
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Terrace/patio
Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC

port tobacco
10.0 out of 10, Exceptional, (9)
"Charming home with so many fun features for our family to enjoy! The kitchen is especially well-equipped for prepping meals for our whole clan."
United States
Liz D.
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
Exterior
Come relax yourself a while

Come relax yourself a while

Mechanicsville
The price is AED 909
AED 2,156 total
includes taxes & fees
14 Nov - 15 Nov
Come relax yourself a while
Outdoor dining
Private Stay By MadlyGiving - At National Harbor

Private Stay By MadlyGiving - At National Harbor

National Harbor/Oxon Hill
The price is AED 3,039
AED 3,529 total
includes taxes & fees
14 Nov - 15 Nov
Private Stay By MadlyGiving - At National Harbor
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (123)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
United States
Chi
The price is AED 657
AED 866 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort
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

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"The front desk staff that checked us in was beyond amazing. He takes pride in his job and boy does it show. His name was Isaiah I believe, we checked in 10/29/25 late at night. "
christy 5-night trip
Posted 5 days ago
Solomons Inn Resort & Marina

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