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Compare 216 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Calloway Drive Retreat | House in Shady Side

9.2 out of 10, Wonderful, (5)
"We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier."
Calloway Drive Retreat | House in Shady Side

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.6 out of 10, Exceptional, (29)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Waterfront Scotland Beach Retreat w/ Private Beach

10.0 out of 10, Exceptional, (41)
"The house is lovely and very comfortable for our group of 8 friends. We would highly recommend!"
Waterfront Scotland Beach Retreat w/ Private Beach

Private Waterfront Retreat with Pool, Hot Tub and Game Room

10.0 out of 10, Exceptional, (23)
"The home was wonderful! So clean and spacious! Very modern beachhouse style home with an amazing view. We loved waking up every morning to see the sunrise. Host was very accommodating and professional. 5/5! Highly recommend this property!"
Private Waterfront Retreat with Pool, Hot Tub and Game Room

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (4)
"We stayed here for four days over July 4th holiday. The house is clean, modern, updated and looked new on the inside. Well equipped with linens, towels, bath products, appliances and accessories. Conveniently located to Herrington Harbor marina for events and weddings. Huge fenced backyard which was great for kids and pets to run around. There were a couple of minor issues with the AC (due to a storm power outage) and the guests before us also didn’t take out their trash so the can was full. But...
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay

2.0 star property
2.0 out of 10, (1)
"The house was being used by someone else at the time of my reservation. I never got the code to the house but i was charged the money. And i never got an answer from the property manager. If you are looking to rent this property save your money because i was scammed."
4-bedroom house in awesome Temple Hills with AC, WiFi. Enjoy your stay

Charming 3-bedroom retreat in White Plains

The price is SAR 409
SAR 573 total
includes taxes & fees
24 Dec - 25 Dec
Charming 3-bedroom retreat in White Plains

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (19)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

9.8 out of 10, Exceptional, (110)
"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

MD/VA/DC. Smallwood State Park

9.6 out of 10, Exceptional, (18)
"I had a research project with a large number of students. The location was excellent for this purpose. The hosts were very receptive to requests. The location is highly recommended!"
MD/VA/DC. Smallwood State Park

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (40)
"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...
The Lazy Crab Beach House - Free beach passes

The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

9.4 out of 10, Exceptional, (42)
"We stayed for the weekend to attend a wedding nearby. The size of the home was perfect for our family of 5. It was clean and well equipped. We enjoyed morning coffee on the deck! The only issue was that one of the queen beds was really hard and not very comfortable. "
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"
Spectacular Waterfront Retreat with Pier

The Cottage

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is SAR 864
SAR 1,614 total
includes taxes & fees
24 Dec - 25 Dec
The Cottage

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (17)
"Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area."
Bay views with kayaks, bikes, fire pit, crabbing and more

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
18-Acre Waterfront Sanctuary: Peace & Privacy
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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Other property types in Southern Maryland

Cozy Cottage with access to and partially obstructed views of the bay.

9.6 out of 10, Exceptional, (14)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
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.