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Southern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Southern Maryland vacation rentals

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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
9.0 out of 10, Wonderful, (16 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 $238
CA $388 total
includes taxes & fees
Nov 10 - Nov 11
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

2. 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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $133
CA $447 total
includes taxes & fees
Dec 1 - Dec 2
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

3. 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 $203
CA $438 total
includes taxes & fees
Nov 9 - Nov 10
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Private kitchen

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 $221
CA $308 total
includes taxes & fees
Nov 15 - Nov 16
Just a getaway piece of property
A lakeside view with chairs and a table, a rainbow, and trees.

5. 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 $322
CA $513 total
includes taxes & fees
Nov 10 - Nov 11
Bright and airy waterfront getaway
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

6. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $213
CA $423 total
includes taxes & fees
Nov 16 - Nov 17
Soul Oasis - home on the Chesapeake Bay
A house with a yellow door and a window with a lamp outside.

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 $190
CA $449 total
includes taxes & fees
Nov 15 - Nov 16
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Pool

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is CA $201
CA $567 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

9. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 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 $293
CA $582 total
includes taxes & fees
Dec 1 - Dec 2
Sunset Cottage - West River Access and Views!
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

10. 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 $212
CA $397 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

11. 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 $226
CA $640 total
includes taxes & fees
Nov 16 - Nov 17
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A two-story house with a deck and a staircase leading to the upper floor.

12. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (151 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 $221
CA $370 total
includes taxes & fees
Nov 16 - Nov 17
MOUNT VERNON RETREAT 🌸
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

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
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is CA $252
CA $612 total
includes taxes & fees
Nov 13 - Nov 14
3-bedroom house in Deale located on Bay many amenities and great views
A deck with outdoor furniture, a red door, and a house with windows.

14. 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 $240
CA $503 total
includes taxes & fees
Nov 9 - Nov 10
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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 $335
CA $762 total
includes taxes & fees
Nov 9 - Nov 10
Anne & Fred`s Leonardtown Home W/ Arcade room!
A spacious living room with a green sofa, glass coffee tables, and a fireplace. A staircase with a railing leads to an upper level.

16. 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 $329
CA $764 total
includes taxes & fees
Nov 9 - Nov 10
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
A covered patio with a view of a lake, furnished with chairs and a table.

17. 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, (20 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $252
CA $505 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Three Adirondack chairs facing a beach with a clear view of the ocean.

18. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $479
CA $757 total
includes taxes & fees
Nov 12 - Nov 13
Plum Point Cottage #14
Fire pit (2)

19. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $478
CA $797 total
includes taxes & fees
Nov 8 - Nov 9
Plum Point Cottage #15
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

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, (22 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is CA $314
CA $589 total
includes taxes & fees
Dec 1 - Dec 2
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

A living room with a sofa, armchairs, a coffee table, and a bookshelf.
Archer Hotel Old Town Alexandria

Archer Hotel Old Town Alexandria

Archer Hotel Old Town Alexandria
Old Town Alexandria

10/10 Excellent

We stayed for 4 nights. We'll located hotel, short walk to the metro train to get to the airport and into DC. Large room, we'll kept and comfortable king size bed. Great staff, friendly and attentive.
Canada
John Allan
Reviewed September 10, 2026
Archer Hotel Old Town Alexandria

Find out more about Southern Maryland

Everything you need to know about Southern Maryland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Maryland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Maryland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Maryland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Maryland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southern Maryland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southern Maryland vacation rentals we have selected for you start as low as CA $132 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southern Maryland rentals

At Expedia, we put the best Southern Maryland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Maryland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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