Southern Maryland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Southern Maryland

Our top choices for Southern Maryland vacation rentals

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Property grounds

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Exterior

**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**
MD/DC/VA Hideaway - Oasis /Jacuzzi w/ 4-bedroom/3-Bath in Fort Washington
Fridge, microwave, oven, stovetop

MD/DC/VA Hideaway - Oasis /Jacuzzi w/ 4-bedroom/3-Bath in Fort Washington

10.0 out of 10, Exceptional, (1)
"Every thing was amazing perfect it was a inspiration for when I purchase my own house the wash cloths where so soft my kids enjoyed being in there own spaces "
MD/DC/VA Hideaway - Oasis /Jacuzzi w/ 4-bedroom/3-Bath in Fort Washington
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Exterior

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

10.0 out of 10, Exceptional, (55)
"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
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (47)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
El Camino
Terrace/patio

El Camino

10.0 out of 10, Exceptional, (48)
"Awesome location and accommodations. Very clean and comfortable. "
El Camino
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, (74)
"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
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Fridge, microwave, oven, stovetop

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (122)
"We are not strangers to the area, my wife having grown up in the area, but each time we stay on the Chesapeake we feel at home. The Hideaway is so nice that you don't want to go back your actual home! It is furnished as if it is a year-round residence, no cheap or mismatched furniture and appliances. We enjoy cooking and the kitchen is has everything you need and it works. The yard and amenities are top notch. If you enjoy bird watching, sit in the back yard and take in the bird activity...
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Tiny, Funky, and Full of Love - Welcome to the Love Shack
Terrace/patio

Tiny, Funky, and Full of Love - Welcome to the Love Shack

9.8 out of 10, Exceptional, (8)
Tiny, Funky, and Full of Love - Welcome to the Love Shack
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, (3)
"My first thought was "gorgeous", when i walked through the door. This was just the weekend I needed. The screened in porch was relaxing. Be ready to take pictures of the sunrise! "
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (147)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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, (9)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
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 ￥25,761
￥47,660 total
includes taxes & fees
Oct 2 - Oct 3
Welcoming 3-bedroom townhome with AC in Waldorf
High River Bank with $1M Sunset View, 3 min to College
Terrace/patio

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (2)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
The price is ￥30,408
￥61,917 total
includes taxes & fees
Sep 29 - Sep 30
High River Bank with $1M Sunset View, 3 min to College
Waterfront Relaxing Getaway
Fridge, microwave, oven, stovetop

Waterfront Relaxing Getaway

10.0 out of 10, Exceptional, (24)
"We enjoyed our stay. Beautiful spot on the water. House had everything we needed and plenty of space for my family."
Waterfront Relaxing Getaway
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Fridge, microwave, oven, stovetop

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

10.0 out of 10, Exceptional, (51)
"Just what we needed for an extended weekend getaway with family. The view of the water was do nice. House was very clean on arrival "
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
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, (15)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
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 ￥21,256
￥63,103 total
includes taxes & fees
Sep 28 - Sep 29
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
The Cottage
Fridge, microwave, oven, stovetop

The Cottage

10.0 out of 10, Exceptional, (8)
"Our stay at the house was great. The host had amazing customer service and the location is beautiful."
The Cottage
Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies
Aerial view

Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies

10.0 out of 10, Exceptional, (155)
"As always, loved our stay here! One of our favorite places for fishing! "
Waterfront Sunset Nature Reserve Kayak Eagle Osprey Snakehead Butterflies
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Maryland Hotel Reviews

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"Enjoyed our stay"
Kimberly 3-night trip
Posted 2 days ago
Solomons Inn Resort & Marina

Find out more about Southern Maryland

Find out more about Southern Maryland

Search for holiday rentals in Southern Maryland on Expedia! You can easily find your home rentals, villas, holiday apartments in Southern Maryland using one of the methods below:

  • View our selection of featured holiday rentals in Southern Maryland
  • Use the map to find apartments and other holiday homes in the Southern Maryland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southern Maryland while they last

Look no further and take a look at our great range of rental properties in Southern Maryland!