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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 $218
CA $381 total
includes taxes & fees
Oct 7 - Oct 8
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 $295
CA $511 total
includes taxes & fees
Oct 7 - Oct 8
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 $172
CA $533 total
includes taxes & fees
Oct 20 - Oct 21
Beachside Oasis with Beach Passes & King Suite by A Haven Away

4. 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 $178
CA $376 total
includes taxes & fees
Oct 19 - Oct 20
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

5. 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 $170
CA $413 total
includes taxes & fees
Oct 12 - Oct 13
The Cozy Crab- Your Charming Haven in Lovely North Beach!

6. 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, (38 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 $223
CA $689 total
includes taxes & fees
Nov 2 - Nov 3
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

7. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is CA $186
CA $472 total
includes taxes & fees
Oct 8 - Oct 9
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

8. 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 10 - Oct 11
Just a getaway piece of property

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 $205
CA $650 total
includes taxes & fees
Oct 7 - Oct 8
Family Beach House: Spacious Deck, Grill & Views

10. 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 $341
CA $835 total
includes taxes & fees
Oct 7 - Oct 8
Anne & Fred`s Leonardtown Home W/ Arcade room!

11. 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)
"Beautiful location "
United States
Jonathan M.
The price is CA $564
CA $1,206 total
includes taxes & fees
Oct 26 - Oct 27
2 Acre Oasis with Private Beach! Family and dog friendly!

12. 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 $327
CA $687 total
includes taxes & fees
Nov 4 - Nov 5
Sunset Cottage - West River Access and Views!

13. 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 $308
CA $713 total
includes taxes & fees
Nov 2 - Nov 3
3-bedroom house in Deale located on Bay many amenities and great views

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, (19 reviews)
"The property was very spacious and clean. Nice neighborhood."
United States
tracey
The price is CA $486
CA $1,087 total
includes taxes & fees
Oct 7 - Oct 8
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

15. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is CA $321
CA $616 total
includes taxes & fees
Oct 7 - Oct 8
Rose Haven Coastal Cottage

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 $439
CA $1,090 total
includes taxes & fees
Oct 21 - Oct 22
Charming Waterfront 3-bedroom house in Piney Point

17. 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 $601
CA $1,118 total
includes taxes & fees
Oct 19 - Oct 20
Tranquil Modern Farmhouse

18. 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 $245
CA $534 total
includes taxes & fees
Nov 2 - Nov 3
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

19. 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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $285
CA $589 total
includes taxes & fees
Oct 21 - Oct 22
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

20. 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 $772
CA $1,680 total
includes taxes & fees
Oct 7 - Oct 8
Lakefront Cabin Near Solomons Island w/ Hot Tub
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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