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In two weeks
26 Sep - 28 Sep
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Vacation Homes in Southern Maryland

Our top choices for Southern Maryland vacation homes

The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.6 out of 10, Exceptional, (8)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (192)
"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Smart TV, printers

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

10.0 out of 10, Exceptional, (1)
"This is a beautiful cottage in a quiet country setting. Our travel had us arriving a little early and Hannah graciously allowed us to check in early. Bathroom doors were attractive and trendy but did not lock or offer complete privacy. "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Exterior

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (72)
"What a great property, wildlife abounds!!! We had a fantastic weekend with family and friends!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (54)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (13)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
Bay views with kayaks, bikes, fire pit, crabbing and more
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Fridge, microwave, oven, stovetop

Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room

9.8 out of 10, Exceptional, (28)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
Welcoming 3-bedroom townhome with AC in Waldorf
3 bedrooms, iron/ironing board, WiFi, bed sheets

Welcoming 3-bedroom townhome with AC in Waldorf

The price is SAR 743
SAR 1,336 total
includes taxes & fees
13 Sep - 14 Sep
Welcoming 3-bedroom townhome with AC in Waldorf
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.0 out of 10, Wonderful, (14)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
Bright and airy waterfront getaway
On the beach, sun loungers

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (17)
"This was our 2nd stay and it won't be our last, it was as amazing as our first time last year. The house is super clean and the beach was so relaxing"
Bright and airy waterfront getaway
Roomy 6 bedroom home in the heart of Solomons, MD
Microwave, oven, stovetop, dishwasher

Roomy 6 bedroom home in the heart of Solomons, MD

9.2 out of 10, Wonderful, (5)
"Stayed for business, completed our project and enjoyed some local eating spots. "
The price is SAR 1,482
SAR 2,668 total
includes taxes & fees
1 Oct - 2 Oct
Roomy 6 bedroom home in the heart of Solomons, MD
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
Property grounds

Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.

10.0 out of 10, Exceptional, (97)
"Great location for wedding guests. "
Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
Exterior

Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths

10.0 out of 10, Exceptional, (79)
"Gorgeous property to stay in and celebrate our daughter's graduation from St Mary's College of Maryland. A paradise so close to campus. "
Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
Waterfront lux cottage with amazing views near DC
Fridge, microwave, oven, stovetop

Waterfront lux cottage with amazing views near DC

9.0 out of 10, Wonderful, (4)
"This property is amazing! What a charming area and town"
Waterfront lux cottage with amazing views near DC
Coastal Haven- Beach w/ BBQ
Beach towels

Coastal Haven- Beach w/ BBQ

10.0 out of 10, Exceptional, (15)
"This house is amazing on a nice quiet street. We enjoyed our stay as it felt like we were home. Clean and cozy a lot of extra room we will be back next year for sure."
Coastal Haven- Beach w/ BBQ
Kentigern at Scotland Yards
Fireplace

Kentigern at Scotland Yards

9.8 out of 10, Exceptional, (131)
"Truly beautiful spot! The owners were a pleasure to deal with. We had a great time!"
The price is SAR 1,970
SAR 3,758 total
includes taxes & fees
7 Oct - 8 Oct
Kentigern at Scotland Yards
4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay
Private kitchen

4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay

2.0 star property
2.0 out of 10, (1)
"The house was being used by someone else at the time of my reservation. I never got the code to the house but i was charged the money. And i never got an answer from the property manager. If you are looking to rent this property save your money because i was scammed."
4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Exterior

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (2)
"The property is newly renovated and very comfortable. Property owner is responsive to any questions, and we enjoyed our stay here. Would recommend it for anyone staying in Shady Side."
The price is SAR 844
SAR 1,980 total
includes taxes & fees
13 Oct - 14 Oct
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage
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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Top Southern Maryland Hotel Reviews

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Holiday Inn Express Washington DC East - Andrews AFB by IHG

10/10 Excellent
"Staff was friendly.. will stay here again!!"
Ashley 1-night trip
Posted 2 days ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG

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Explore a world of travel with Expedia