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Find Winery Hotels in Southern Maryland, MD

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Check availability on Southern Maryland Winery Hotels

Our top choices for Southern Maryland hotels with winery

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.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (48)
"We love this place!"
United States
Joan K.
The price is ￥16,687
￥38,994 total
includes taxes & fees
Dec 18 - Dec 19
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.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is ￥28,046
￥46,628 total
includes taxes & fees
Dec 16 - Dec 17
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.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.6 out of 10, Exceptional, (5)
"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 ￥28,046
￥55,989 total
includes taxes & fees
Dec 17 - Dec 18
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8)
"Everything was amazing. "
United States
Lorie S.
The price is ￥29,012
￥57,838 total
includes taxes & fees
Dec 16 - Dec 17
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Exterior
Come relax yourself a while

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is ￥38,563
￥90,135 total
includes taxes & fees
Dec 16 - Dec 17
Come relax yourself a while
Outdoor dining
Private Stay By MadlyGiving - At National Harbor

Private Stay By MadlyGiving - At National Harbor

Private Stay By MadlyGiving - At National Harbor
National Harbor/Oxon Hill
Private Stay By MadlyGiving - At National Harbor
In-room safe, individually decorated, individually furnished, desk
Holiday Inn Express Washington DC Downtown by IHG

Holiday Inn Express Washington DC Downtown by IHG

Holiday Inn Express Washington DC Downtown by IHG
2.5 star property
Downtown Washington D.C.
8.2 out of 10, Very Good, (2078)
"our stay was great!"
United States
Maria
The price is ￥12,309
￥14,272 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Holiday Inn Express Washington DC Downtown by IHG
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ￥22,327
￥30,350 total
includes taxes & fees
Dec 16 - Dec 17
Kent Island Resort
Terrace/patio
Ramada by Wyndham Triangle/Quantico

Ramada by Wyndham Triangle/Quantico

Ramada by Wyndham Triangle/Quantico
3.0 star property
Triangle
7.6 out of 10, Good, (1003)
"Antique hotel, not in a good way. Clean bed, nominally clean room, the breakfast was underwhelming to be kind. Close to the MCM, and convenient to interstate."
United States
james
The price is ￥11,697
￥13,334 total
includes taxes & fees
Dec 22 - Dec 23
Ramada by Wyndham Triangle/Quantico
Full-size fridge, microwave, stovetop, dishwasher
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (181)
"The staff was extremely pleasant and enjoyable to work with!! "
United States
Laura
The price is ￥13,088
￥14,920 total
includes taxes & fees
Dec 19 - Dec 20
Candlewood Suites Annapolis by IHG
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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