Holiday Homes in Southern Maryland

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Featured Holiday Homes in Southern Maryland

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

10.0 out of 10, Exceptional, (51)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

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

9.8 out of 10, Exceptional, (46)
"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

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

9.6 out of 10, Exceptional, (7)
"Modern, Fresh, Clean! No complaints at all!"
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (168)
"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "
Waterfront Wildlife Retreat on the Patuxent River

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

9.8 out of 10, Exceptional, (70)
"We enjoyed the property lots of wildlife around enjoyed kayaking and crabing . "
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!

Wooded Hillside Retreat in Waldorf, MD - Top 10% and Guest favorite elsewhere

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place has been great! Owners are very communicative and helpful. We have enjoyed this house and would love to return."
Wooded Hillside Retreat in Waldorf, MD - Top 10% and Guest favorite elsewhere

Charming Waterfront Getaway with Private Dock

10.0 out of 10, Exceptional, (2)
"Our 4 day trip to Lusby, MD was one that we will not forget. Your home exceeded all our expectations! Our family of 7 felt very comfortable and not a single person had a negative thing to say. (Which doesn’t come easy with 2 teenagers!) The entire home was well equipped and stocked, particularly the kitchen. Between the kayaks, crab pots, dock, (the amazing AM/FM radio in the living room) the expansive decks, the two living areas, the abundant charging/docking stations, we never found ourselves...
Charming Waterfront Getaway with Private Dock

**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**

New! Cozy River Cottage with great views of the water!

9.6 out of 10, Exceptional, (10)
"A very nice house with an amazing view 10/10 recommend"
New! Cozy River Cottage with great views of the water!

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (17)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes

2 Mi to Lighthouse: Waterfront Home w/ Dock!

8.6 out of 10, Excellent, (38)
"we stayed for work, plenty of things to do in the area. plenty of space in the house. everything was clean."
2 Mi to Lighthouse: Waterfront Home w/ Dock!

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (30)
"We had an amazing stay in this beautiful house! Inside was massive perfectly set up for our needs. Outside had stunning views and there is nothing better than being on the waters edge. The owners were easy to communicate with and they had everything ready in a timely manner for our check in. We didn’t get a chance to catch any crabs but we will definitely stay here again to try our hand at that."
WATERFRONT!!! The River's Roost on The Patuxent River

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (8)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!

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

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

10.0 out of 10, Exceptional, (78)
"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

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (55)
"Great stay"
The Lazy Crab Beach House - Free beach passes

Riverside House w/ Kayaks, Piano & Fireplace

8.8 out of 10, Excellent, (16)
"Exploring via water on the kayaks was a beautiful way to see the area!! "
Riverside House w/ Kayaks, Piano & Fireplace
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southern Maryland Hotel Reviews

Find out more about Southern Maryland

Find out more about Southern Maryland

Southern Maryland Holiday Homes information

Number of reviews
30
Accommodation
298 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia