Search Holiday Homes in Southern Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Southern Maryland holiday homes

Exterior

MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (132 reviews)
"Everything was as advertised and very clean"
United States
Jamie
The price is £200
includes taxes & fees
3 May - 4 May
MOUNT VERNON RETREAT 🌸
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is £323
includes taxes & fees
14 Apr - 15 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"Delightful one-night stay! Place was clean, quiet, convenient and very comfortable. Especially grateful that our beloved dog was welcomed"
United States
Elaine D.
The price is £274
includes taxes & fees
19 Apr - 20 Apr
Walk to Beach! King Bed & Free Beach Passes
Smart TV, books

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is £315
includes taxes & fees
14 Apr - 15 Apr
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is £581
includes taxes & fees
14 Apr - 15 Apr
4-BR Waterfront Turret Home
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!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is £367
includes taxes & fees
15 Apr - 16 Apr
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Smart TV, fireplace, computer monitors, printers

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (7 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is £452
includes taxes & fees
16 Apr - 17 Apr
Tranquil Modern Farmhouse
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is £361
includes taxes & fees
20 Apr - 21 Apr
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is £295
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home for a girls weekend away. The view is spectacular, host was communicative, and lots of thoughtful small touches throughout the home and the experience. Thank you for a wonderful stay! "
United States
Katie K.
The price is £331
includes taxes & fees
14 Apr - 15 Apr
Sunset Cottage - West River Access and Views!
Fridge, microwave, stovetop, dishwasher

Cozy Private Home | Near DC & Military Bases

Cozy Private Home | Near DC & Military Bases
Indian Head
The price is £284
includes taxes & fees
16 Apr - 17 Apr
Cozy Private Home | Near DC & Military Bases
View from property

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is £335
includes taxes & fees
14 Apr - 15 Apr
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Dining

Welcoming 3-bedroom townhome with AC in Waldorf

Welcoming 3-bedroom townhome with AC in Waldorf
Waldorf
7.6 out of 10, Good, (5 reviews)
"Nice cozy clean location"
United States
Anonymous traveller
The price is £339
includes taxes & fees
14 Apr - 15 Apr
Welcoming 3-bedroom townhome with AC in Waldorf
Interior

Modern and Spacious 4-bedroom house close to DC and National Harbor

Modern and Spacious 4-bedroom house close to DC and National Harbor
Fort Washington
10.0 out of 10, Exceptional, (3 reviews)
"Everything was wonderful "
United States
david h.
The price is £477
includes taxes & fees
14 Apr - 15 Apr
Modern and Spacious 4-bedroom house close to DC and National Harbor
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is £432
includes taxes & fees
14 Apr - 15 Apr
Charming Waterfront 3-bedroom house in Piney Point
TV, fireplace, video games, books

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is £759
includes taxes & fees
15 Apr - 16 Apr
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
TV

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Waldorf
The price is £406
includes taxes & fees
14 Apr - 15 Apr
Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Outdoor dining

Fall is here!!! Backyard retreat waiting for you and your guest.

Fall is here!!! Backyard retreat waiting for you and your guest.
Waldorf
6.0 out of 10, (2 reviews)
"The property is beautiful. Furniture is comfortable (beds, sofa, and chairs). Everything was clean when we checked in. The patio/deck was beautiful. We were able to sit out back and enjoy the evening although it was chilly because of the heating lamp. It was a nice weekend gateway for the ladies - we are already planning the next one! I highly recommend staying here."
United States
Jackie P.
The price is £306
includes taxes & fees
14 Apr - 15 Apr
Fall is here!!! Backyard retreat waiting for you and your guest.
Interior

Charming 4-bedroom house with WiFi, fitness room in superb Waldorf

Charming 4-bedroom house with WiFi, fitness room in superb Waldorf
Waldorf
The price is £1,412
includes taxes & fees
14 Apr - 15 Apr
Charming 4-bedroom house with WiFi, fitness room in superb Waldorf
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

Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

2/10 Terrible
"Hallways smelt terrible, like a stagnant cigarette smell even thought we were in non smoking. Breakfast was dry muffins, cereal and nasty tasting coffee. "
Jason 1-night trip
Posted 2 hours ago
Econo Lodge Andrews Air Force Base

Find out more about Southern Maryland

Southern Maryland Holiday Homes information

Number of reviews
364
Accommodation
250 Holiday Homes
Lowest Price
£200
Highest Price
£1,412

Explore a world of travel with Expedia