Southern Maryland Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, 107 reviews
"The property is located in a small neighborhood right by the water. While there are houses fairly close it is quiet with beautiful views. The house is clean and has good appliances/wifi for a comfortable stay. It is a one bedroom with a big bathroom and living room. The screened in patio is good to avoid the mosquitos. One note is for those with mobility issues, the shower/bathtub has a high ledge with a thicker width to get in/out."
The price is $185
$282 total
includes taxes & fees
Jun 17 - Jun 18
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Lobby
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
3.0 star property
10.0 out of 10, Exceptional, 1 review
"Suite was clean. Quiet you could not hear neighbors."
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Wyndham at National Harbor - 2 Bedroom Deluxe
Lobby
Wyndham at National Harbor - 2 Bedroom Deluxe
4.0 star property
10.0 out of 10, Exceptional, 5 reviews
"Great condo! Very comfortable and perfect location for shopping and dining."
Wyndham at National Harbor - 2 Bedroom Deluxe
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Private Beach Front Getaway at The Sunshine Beach Cottage.
On the beach, sun loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, 47 reviews
"Comfortable, clean home directly on the Chesapeake Bay."
Private Beach Front Getaway at The Sunshine Beach Cottage.
Piney Point, private , Beach Front Cottage
Property grounds
Piney Point, private , Beach Front Cottage
10.0 out of 10, Exceptional, 75 reviews
"This place is incredible!!!! What an amazing property and beautiful home."
Piney Point, private , Beach Front Cottage
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, 25 reviews
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, 4 reviews
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Waterfront Relaxing Getaway
Beach
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, 11 reviews
"I was looking for a nice, quiet, and relaxing, vacation. This property did not disappoint. The house was comfortable, cozy, well stocked, and so clean. The view is incredible. Just sitting outside watching the river was so "Zen". I had one of the most restful vacations ever. I was there for a little over two weeks and I would have stayed longer if I could have, Kim, the host, was very friendly and helpful. I look forward to staying at this beautiful property again."
The price is $185
$421 total
includes taxes & fees
Jun 16 - Jun 17
Waterfront Relaxing Getaway
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, 102 reviews
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Beach nearby
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, 35 reviews
"Great place for a short moms getaway. Walking distances to many things. Heard live music from the porch. House is spacious and extremely clean"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, 6 reviews
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is $130
$285 total
includes taxes & fees
Jun 17 - Jun 18
Soul Oasis - home on the Chesapeake Bay
The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, 39 reviews
"It was clean and had everything we needed. We had a very comfortable stay. There are one or two steps between many of the rooms so keep that in mind."
The Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, 29 reviews
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Dee's Lounge, Your Relaxation Oasis
Pool
Dee's Lounge, Your Relaxation Oasis
9.8 out of 10, Exceptional, 7 reviews
"This home was beautiful and very accommodating for my guest and I. It was nice, cozy and clean and I didn’t need anything because she had it there. I will definitely book this again when I’m in the area. Thank you for your hospitality."
Dee's Lounge, Your Relaxation Oasis
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, 171 reviews
"Groomsmen stayed here for wedding. Great experience in a beautiful location. Swimming and kayaking right out the back door. Owners were very kind and helpful. Definitely recommend this beautiful spot."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Fridge, microwave, oven, stovetop
Private Waterview Estate with 4 bedroom Suites & Hot Tub
9.8 out of 10, Exceptional, 18 reviews
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites & Hot Tub
Chesapeake Bay Vacation Rental w/ Boat Dock!
View from property
Chesapeake Bay Vacation Rental w/ Boat Dock!
8.8 out of 10, Excellent, 5 reviews
"It was not as clean as it should have been. When i pay to stay somewhere, i expect clean."
Chesapeake Bay Vacation Rental w/ Boat Dock!
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Beach | Beach nearby, sun loungers
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, 51 reviews
"What a fantastic property! We loved staying here and our family had such a great time exploring. Sadly it was a drizzly, dreary weekend but we had one nice day to go down to the beach and the kids enjoyed playing in the water. We loved the variety of porches to sit on and have different views and there was plenty of room for the kids to play indoors when it was raining. Overall a great experience. Thank you!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
10.0 out of 10, Exceptional, 4 reviews
"We were in town for a friends wedding. This was the perfect location as it was right in between the Catholic Church for the nuptial mass and the reception site. This place certainly did not disappoint. There was plenty of space for our large family, the home was well equipped and stocked with the necessary items. It was a relatively short stay, but I wish we had a bit more time and better weather to enjoy the use of kayaks - our one free morning was a bit chilly for us Florida folks, and we had...
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Lobby
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
2.0 star property
10.0 out of 10, Exceptional, 2 reviews
"Inside: We had a two-room setup (king bed and adjoining bathroom that had a stall and tub; then two queen beds and bath off the dining room). The room was very comfortable and spacious. The kitchen was great. We were given great starter amenities; The only issue we had was that we were unclear on whether we could ask for more or the cleaning staff to come in. The vibe seemed weird around Vrbo customers; it was not worth it to us to kick up dust. Additionally, the second floor community amenities...
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Don't see what you're looking for?
See all available properties in Southern Maryland
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.

Other types of properties in Southern Maryland you may be interested in

Gaylord National Resort & Convention Center
Exterior
Gaylord National Resort & Convention Center
4.0 star property
8.4 out of 10, Very Good, 1,005 reviews
"It was amazing and has everything!"
The price is $246
$317 total
includes taxes & fees
Jul 1 - Jul 2
Gaylord National Resort & Convention Center
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
Exterior
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
2.5 star property
8.0 out of 10, Very Good, 993 reviews
"Great spot. Less than a mile from the green line. "
The price is $107
$121 total
includes taxes & fees
Jun 30 - Jul 1
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
Hampton Inn & Suites National Harbor - Alexandria Area
Exterior
Hampton Inn & Suites National Harbor - Alexandria Area
2.5 star property
8.8 out of 10, Excellent, 1,000 reviews
"No airport shuttle, otherwise it would have been 5 stars."
The price is $144
$170 total
includes taxes & fees
Jul 1 - Jul 2
Hampton Inn & Suites National Harbor - Alexandria Area
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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Southern Maryland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Recent reviews of Southern Maryland properties
Expedia verified reviews

Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

5/5 Excellent
"Staff"
A verified traveler stayed at Econo Lodge Andrews Air Force Base
Posted 1 day ago
Econo Lodge Andrews Air Force Base