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Winery Hotels & Resorts in Southern Maryland from NZ$147
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Our top choices for Southern Maryland hotels with winery
MOUNT VERNON RETREAT 🌸
MOUNT VERNON RETREAT 🌸Alexandria
9.8 out of 10, Exceptional, (128)
"We had a great time. The property was clean and peaceful. It was far enough away from things to be quiet and relaxing but close enough to get to everything we needed to in a good amount of time"
Carolyn B.
The price is NZ$387
includes taxes & fees
5 Jan - 6 Jan 2026
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!"
Joan K.
The price is NZ$470
includes taxes & fees
29 Dec - 30 Dec
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 "
karen
The price is NZ$513
includes taxes & fees
29 Dec - 30 Dec
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. "
Carrie K.
The price is NZ$667
includes taxes & fees
4 Jan - 5 Jan 2026
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. "
Lorie S.
The price is NZ$685
includes taxes & fees
14 Jan - 15 Jan 2026
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
Riverfront Retreat-HotTubIDock|Fenced YardINear DCport tobacco
10.0 out of 10, Exceptional, (9)
"Excellent "
Joseph T.
The price is NZ$989
includes taxes & fees
30 Dec - 31 Dec
Holiday Inn Express Washington DC Downtown by IHG
Holiday Inn Express Washington DC Downtown by IHGDowntown Washington D.C.
8.2 out of 10, Very good, (2088)
"our stay was great!"
Maria
The price is NZ$157
includes taxes & fees
8 Jan - 9 Jan 2026
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
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