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Southern Maryland Vacation Rentals

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Our top choices for Southern Maryland vacation rentals

1. 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 $219
CA $385 total
includes taxes & fees
Oct 15 - Oct 16
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 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 $294
CA $512 total
includes taxes & fees
Oct 15 - Oct 16
Bright and airy waterfront getaway

3. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $137
CA $479 total
includes taxes & fees
Oct 19 - Oct 20
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $169
CA $411 total
includes taxes & fees
Oct 17 - Oct 18
The Cozy Crab- Your Charming Haven in Lovely North Beach!

5. 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 $369 total
includes taxes & fees
Oct 27 - Oct 28
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

6. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $331
CA $700 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!

7. 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 $340
CA $838 total
includes taxes & fees
Oct 18 - Oct 19
Anne & Fred`s Leonardtown Home W/ Arcade room!

8. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay at this home in North Beach, MD! The house was clean, comfortable, and conveniently located near The Inn at Herrington Harbour, making it a great choice for our visit. Everything worked well for our stay, and we appreciated having a nice place to relax. We would happily recommend this property to anyone looking for a comfortable and convenient place to stay in the area!"
United States
Jeremy P.
The price is CA $320
CA $619 total
includes taxes & fees
Oct 19 - Oct 20
Rose Haven Coastal Cottage

9. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $463
CA $822 total
includes taxes & fees
Oct 21 - Oct 22
Plum Point Cottage #15

10. 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, (40 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 $211
CA $658 total
includes taxes & fees
Nov 3 - Nov 4
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

11. 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 $205
CA $651 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views

12. 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.
Riverfront Retreat-HotTubIDock|Fenced YardINear DC

13. 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 $485
CA $1,073 total
includes taxes & fees
Nov 9 - Nov 10
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

14. 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 $224
CA $323 total
includes taxes & fees
Oct 18 - Oct 19
Just a getaway piece of property

15. 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)
The price is CA $438
CA $1,088 total
includes taxes & fees
Nov 4 - Nov 5
Charming Waterfront 3-bedroom house in Piney Point

16. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (66 reviews)
"We were thrilled with this vacation spot! From the cleanliness of the home to the absolutely amazing views from every window and a beautiful sunset almost every day, we just loved it!"
United States
J B.
The price is CA $563
CA $1,204 total
includes taxes & fees
Oct 27 - Oct 28
2 Acre Oasis with Private Beach! Family and dog friendly!

17. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $256
CA $621 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom house in Deale located on Bay many amenities and great views

18. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $387
CA $660 total
includes taxes & fees
Oct 21 - Oct 22
Plum Point Cottage #17

19. Mandale Ct - Two-Story Shared Home

Mandale Ct - Two-Story Shared Home
2.0 star property
Fort Washington
The price is CA $205
CA $477 total
includes taxes & fees
Oct 25 - Oct 26
Mandale Ct - Two-Story Shared Home

20. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is CA $244
CA $538 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
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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