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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 $216
CA $381 total
includes taxes & fees
Oct 19 - Oct 20
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2. 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 $168
CA $420 total
includes taxes & fees
Oct 19 - Oct 20
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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 $136
CA $476 total
includes taxes & fees
Oct 28 - Oct 29
Beachside Oasis with Beach Passes & King Suite by A Haven Away

4. 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 $223
CA $321 total
includes taxes & fees
Oct 22 - Oct 23
Just a getaway piece of property

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 $183
CA $382 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

6. 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 $293
CA $502 total
includes taxes & fees
Oct 19 - Oct 20
Bright and airy waterfront getaway

7. Mandale Ct - Two-Story Shared Home

Mandale Ct - Two-Story Shared Home
2.0 star property
Fort Washington
The price is CA $372
CA $665 total
includes taxes & fees
Oct 20 - Oct 21
Mandale Ct - Two-Story Shared Home

8. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (149 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 $247
CA $436 total
includes taxes & fees
Nov 1 - Nov 2
MOUNT VERNON RETREAT 🌸

9. 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 $204
CA $648 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views

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)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is CA $199
CA $642 total
includes taxes & fees
Nov 9 - Nov 10
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

11. 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 $346
CA $715 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!

12. Cozy Private Home | Near DC & Military Bases

Cozy Private Home | Near DC & Military Bases
Indian Head
10.0 out of 10, Exceptional, (2 reviews)
"The place was a great home base to relax in after a long day out. The massage chair was really helpful after a day of driving."
United States
Matt T.
Cozy Private Home | Near DC & Military Bases

13. 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 $243
CA $535 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

14. 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 $255
CA $617 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom house in Deale located on Bay many amenities and great views

15. 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 $338
CA $833 total
includes taxes & fees
Oct 19 - Oct 20
Anne & Fred`s Leonardtown Home W/ Arcade room!

16. Mandale Ct - Welcoming Two-Story Shared Home in Fort Washington

Mandale Ct - Welcoming Two-Story Shared Home in Fort Washington
Fort Washington
The price is CA $245
CA $494 total
includes taxes & fees
Oct 23 - Oct 24
Mandale Ct - Welcoming Two-Story Shared Home in Fort Washington

17. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $462
CA $774 total
includes taxes & fees
Oct 19 - Oct 20
Plum Point Cottage #14

18. 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, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $283
CA $587 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

19. 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, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is CA $560
CA $1,197 total
includes taxes & fees
Oct 26 - Oct 27
2 Acre Oasis with Private Beach! Family and dog friendly!

20. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (20 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is CA $317
CA $623 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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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