Holiday Rentals in Southern Maryland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Southern Maryland

Property grounds
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
9.8 out of 10, Exceptional, (107)
"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 €244
per night
28 May - 29 May
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Lobby
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
3.0 star property
10.0 out of 10, Exceptional, (1)
"Suite was clean. Quiet you could not hear neighbors."
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Beach
Waterfront Relaxing Getaway
10.0 out of 10, Exceptional, (11)
"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 €399
per night
4 Jun - 5 Jun
Waterfront Relaxing Getaway
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Lobby
Wyndham at National Harbor - 2 Bedroom Deluxe
4.0 star property
10.0 out of 10, Exceptional, (5)
"Great condo! Very comfortable and perfect location for shopping and dining."
Wyndham at National Harbor - 2 Bedroom Deluxe
Lobby
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
2.0 star property
10.0 out of 10, Exceptional, (1)
"Staff was awesome and nice fast check in everything was clean"
Luxurious Club Wyndham National Harbor, 2 Bedroom Deluxe Suite
Beach
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
10.0 out of 10, Exceptional, (51)
"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
Beach nearby
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (34)
"Clean! Great location. Easy check in"
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
On the beach, sun-loungers, beach towels
Private Beach Front Getaway at The Sunshine Beach Cottage.
9.8 out of 10, Exceptional, (45)
"My husband and I have been to this cottage once before. It's our secret getaway. It has everything you need plus the beach is just a few feet away. You can't find another place like this one!"
Private Beach Front Getaway at The Sunshine Beach Cottage.
Exterior
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (6)
"Pleasant relaxing time. We were pleased and impress to locate this property"
The price is €274
per night
4 Jun - 5 Jun
Soul Oasis - home on the Chesapeake Bay
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (73)
"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Smart TV
Luxury room near National Habor
The price is €83
per night
30 May - 31 May
Luxury room near National Habor
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (29)
"👍👍"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (39)
"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
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (24)
"This house and property is GORGEOUS. Well maintained, beautiful setting. Amazing amenities (pool, hot tub) which enhanced our stay. We had no problem finding multiple places to all hang out and chat- the living room with plenty of seating, the dining room table with seating for at least 14, and outside in the hot tub. It was a perfect setting for valuable time away with friends! Additionally, the owner was STELLAR in communication. I very much appreciated his quick and attentive responses...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"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
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, (101)
"The house was very well maintained, beach access and views were wonderful. This location was very quiet, and if you are a nature lover this location is perfect. Many miles to walk and explore, lots of birds to watch. Very enjoyable weekend. Hope to return."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Property grounds
Quaint cottage with serene water view!
10.0 out of 10, Exceptional, (24)
"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"
Quaint cottage with serene water view!
Lobby
Wyndham National Harbor - 2 Bedroom Deluxe
4.0 star property
Wyndham National Harbor - 2 Bedroom Deluxe
Pool
Dee's Lounge, Your Relaxation Oasis
9.8 out of 10, Exceptional, (7)
"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
Beach nearby, sun-loungers, beach towels
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
10.0 out of 10, Exceptional, (52)
"We enjoyed out stay very much in February. It was so quiet and nice. Very very clean! Three generations of family came and loved. The sunroom with the view of the water was amazing and nice and toasty for our winter getaway. Thank you Diane and Harold for being so helpful, all the extra nice touches you added, and sharing your lovely cottage with us! We would love to visit again."
WATERFRONT GETAWAY- Charming Waterfront Cottage on St Clements Bay
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

Exterior
Gaylord National Resort & Convention Center
4.0 star property
8.4 out of 10, Very good, (1007)
"Beautiful property and great accommodations. "
The price is €283
per night
6 Jun - 7 Jun
Gaylord National Resort & Convention Center
Exterior
Hampton Inn & Suites National Harbor - Alexandria Area
2.5 star property
8.8 out of 10, Excellent, (1002)
"Nice staff"
The price is €166
per night
6 Jun - 7 Jun
Hampton Inn & Suites National Harbor - Alexandria Area
Coffee service
Red Roof Inn PLUS+ Washington DC - Oxon Hill 
2.5 star property
6.8 out of 10, (1002)
"Bb"
The price is €108
per night
23 Jun - 24 Jun
Red Roof Inn PLUS+ Washington DC - Oxon Hill 
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southern Maryland holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southern Maryland holiday rentals we have selected for you start as low as €244 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 holiday 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 holiday.

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
"It was decent my very first time stayin yhere but I'll go back again fo sho!"
A verified traveller stayed at Econo Lodge Andrews Air Force Base
Posted 2 days ago
Econo Lodge Andrews Air Force Base