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Southern Maryland Vacation Rentals

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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, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is CA $301
CA $514 total
includes taxes & fees
Sep 11 - Sep 12
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)
"The owner was very nice "
United States
karen
The price is CA $211
CA $368 total
includes taxes & fees
Sep 17 - Sep 18
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (60 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $209
CA $437 total
includes taxes & fees
Sep 11 - Sep 12
Soul Oasis - home on the Chesapeake Bay

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 $597
CA $1,606 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Cabin Near Solomons Island w/ Hot Tub

5. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (144 reviews)
"Very comfortable and clean property. Comfortable beds! The hosts are excellent communicators and very kind. Close to the mt Vernon trail."
United States
Dana H.
The price is CA $217
CA $394 total
includes taxes & fees
Sep 11 - Sep 12
MOUNT VERNON RETREAT 🌸

6. 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 $637
CA $1,171 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

7. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
10.0 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay at this property and will definitely be back again!"
United States
Jeff and Nancy B.
The price is CA $332
CA $799 total
includes taxes & fees
Sep 9 - Sep 10
Riverfront Retreat-HotTubIDock|Fenced YardINear DC

8. 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 $570
CA $1,140 total
includes taxes & fees
Sep 10 - Sep 11
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

9. 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 $330
CA $808 total
includes taxes & fees
Sep 7 - Sep 8
Anne & Fred`s Leonardtown Home W/ Arcade room!

10. 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 $705
CA $1,578 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Cabin Near Solomons Island w/ Hot Tub

11. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $414
CA $1,000 total
includes taxes & fees
Sep 8 - Sep 9
4-BR Waterfront Turret Home

12. Charming 4-House in central Waldorf

Charming 4-House in central Waldorf
Waldorf
The price is CA $586
CA $1,111 total
includes taxes & fees
Sep 5 - Sep 6
Charming 4-House in central Waldorf

13. Modern Stay Hottub and Pool

Modern Stay Hottub and Pool
Upper Marlboro
10.0 out of 10, Exceptional, (1 review)
"Everything looked exactly like the pictures ! I loved the place this will be my go to !"
United States
Diana H.
The price is CA $717
CA $1,194 total
includes taxes & fees
Sep 7 - Sep 8
Modern Stay Hottub and Pool

14. 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, (18 reviews)
"The property was very spacious and clean. Nice neighborhood."
United States
tracey
The price is CA $397
CA $958 total
includes taxes & fees
Sep 9 - Sep 10
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

15. 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 $637
CA $1,344 total
includes taxes & fees
Sep 17 - Sep 18
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

16. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is CA $473
CA $1,101 total
includes taxes & fees
Sep 7 - Sep 8
Charming Waterfront 3-bedroom house in Piney Point

17. Luxury 3,000 Sq Ft Multi‑Suite Retreat • Designer Interiors • Workspaces

Luxury 3,000 Sq Ft Multi‑Suite Retreat • Designer Interiors • Workspaces
Welcome
The price is CA $590
CA $1,967 total
includes taxes & fees
Sep 6 - Sep 7
Luxury 3,000 Sq Ft Multi‑Suite Retreat • Designer Interiors • Workspaces

18. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is CA $415
CA $787 total
includes taxes & fees
Sep 9 - Sep 10
Sunset Cottage - West River Access and Views!

19. 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, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $101
CA $438 total
includes taxes & fees
Sep 9 - Sep 10
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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 $201
CA $651 total
includes taxes & fees
Sep 14 - Sep 15
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.
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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.

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