A heron standing in a golden-hued wetland with a bird flying in the background.

Southern Maryland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

Our top choices for Southern Maryland vacation rentals

1. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is CA $290
CA $473 total
includes taxes & fees
Sep 23 - Sep 24
Bright and airy waterfront getaway

2. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $215
CA $354 total
includes taxes & fees
Sep 23 - Sep 24
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

3. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is CA $220
CA $319 total
includes taxes & fees
Oct 2 - Oct 3
Just a getaway piece of property

4. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is CA $650
CA $1,655 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront Cabin Near Solomons Island w/ Hot Tub

5. Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
La Plata
9.6 out of 10, Exceptional, (4 reviews)
"Cane for a weekend of Faith and Fun and this is exactly what we needed. Comfortably suited our 10 needs and so much more. Peaceful, serene, beautiful animals, game room, so much to say. Hostess with the mostest!!!! Charity is a gem! My church family will be back!!!!!"
United States
Wadiya D.
The price is CA $793
CA $1,419 total
includes taxes & fees
Sep 23 - Sep 24
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

6. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $169
CA $363 total
includes taxes & fees
Sep 30 - Oct 1
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

7. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $766
CA $1,658 total
includes taxes & fees
Sep 23 - Sep 24
Lakefront Cabin Near Solomons Island w/ Hot Tub

8. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $210
CA $436 total
includes taxes & fees
Sep 30 - Oct 1
Soul Oasis - home on the Chesapeake Bay

9. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is CA $633
CA $1,152 total
includes taxes & fees
Oct 5 - Oct 6
Tranquil Modern Farmhouse

10. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $648
CA $1,191 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

11. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $335
CA $822 total
includes taxes & fees
Sep 27 - Sep 28
Anne & Fred`s Leonardtown Home W/ Arcade room!

12. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (146 reviews)
"What a beautiful and quaint little place to stay! So peaceful and the hosts were absolutely delightful! We will definitely be back!"
United States
Tiffany Z.
The price is CA $219
CA $395 total
includes taxes & fees
Oct 18 - Oct 19
MOUNT VERNON RETREAT 🌸

13. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $421
CA $1,018 total
includes taxes & fees
Sep 28 - Sep 29
4-BR Waterfront Turret Home

14. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $135
CA $485 total
includes taxes & fees
Sep 28 - Sep 29
Beachside Oasis with Beach Passes & King Suite by A Haven Away

15. SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
Fort Washington
9.6 out of 10, Exceptional, (19 reviews)
"The property was very spacious and clean. Nice neighborhood."
United States
tracey
The price is CA $479
CA $1,071 total
includes taxes & fees
Sep 29 - Sep 30
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

16. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $202
CA $640 total
includes taxes & fees
Sep 23 - Sep 24
Family Beach House: Spacious Deck, Grill & Views

17. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $382
CA $644 total
includes taxes & fees
Sep 23 - Sep 24
Plum Point Cottage #17

18. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $646
CA $1,388 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

19. 43 acre private retreat for the whole family within minutes of DC

43 acre private retreat for the whole family within minutes of DC
Nanjemoy
10.0 out of 10, Exceptional, (2 reviews)
"Great place, very private with expansive outdoor space. Host were very accommodating. Will definitely book again."
United States
Khanh N.
The price is CA $1,252
CA $2,020 total
includes taxes & fees
Sep 28 - Sep 29
43 acre private retreat for the whole family within minutes of DC

20. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is CA $198
CA $613 total
includes taxes & fees
Sep 29 - Sep 30
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southern Maryland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia