Search Holiday Rentals in Southern Maryland

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Find properties with these dates

Tonight
May 14 - May 15
Tomorrow
May 15 - May 16
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Top Holiday Rentals in Southern Maryland

Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
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 £342
per night
2 Jun - 3 Jun
Waterfront Relaxing Getaway
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (28)
"The house was great and nice area!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
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Beach | Beach nearby, sun-loungers
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
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (23)
"The Lazy Crab was a wonderful place to stay for a girls weekend away! Everything was provided to make the stay easy, comfortable and fun! If we needed it it was there. The location was perfect… great restaurants right down the street and the bay just beyond… an easy walk away. The owner was responsive when we messaged. All good and I would stay again. Thank you!"
The Lazy Crab Beach House - Free beach passes
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
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
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 £236
per night
22 May - 23 May
Soul Oasis - home on the Chesapeake Bay
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (3)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Fridge, microwave, oven, stovetop
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (170)
"We spent the weekend relaxing in the outdoors with family. We kayaked, had an outdoor fire and enjoyed the wildlife that floated or flew by."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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
Property grounds
Waterfront Lusby Home w/ Deck & Stunning Views!
10.0 out of 10, Exceptional, (1)
Waterfront Lusby Home w/ Deck & Stunning Views!
Property grounds
Studio on the Bay.
10.0 out of 10, Exceptional, (15)
"Quiet, clean and charming."
Studio on the Bay.
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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!
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (60)
"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"
Mid-Century Modern and Marvelous on the Bay
On the beach
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
10.0 out of 10, Exceptional, (63)
"Enjoyed the location right on the water. Will definitely be back!"
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Property grounds
Tranquil Port Republic Home w/ Water Views!
10.0 out of 10, Exceptional, (12)
"This place was just what my family needed to reconnect. Amazing views and atmosphere"
Tranquil Port Republic Home w/ Water Views!
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 £210
per night
21 May - 22 May
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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.
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
Hampton Inn & Suites National Harbor - Alexandria Area
2.5 star property
8.8 out of 10, Excellent, (1000)
"Too many kids no room to eat at breakfast and the tables and around thefood was dirty due to the kids getting their own food."
The price is £143
per night
6 Jun - 7 Jun
Hampton Inn & Suites National Harbor - Alexandria Area
Exterior
Gaylord National Resort & Convention Center
4.0 star property
8.4 out of 10, Very good, (1006)
"Lovely "
The price is £308
per night
31 May - 1 Jun
Gaylord National Resort & Convention Center
Exterior
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
2.5 star property
8.0 out of 10, Very good, (976)
"Clean room. Was not the room I booked on expedia but it worked for the night. "
The price is £114
per night
19 May - 20 May
Holiday Inn Express Washington DC East - Andrews AFB, an IHG Hotel
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.