Search Vacation Homes in Southern Maryland

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Compare 223 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (87)
"This lovely home sets in a beautful location. The hosts are available and accommodating. They are definitely available if needed. The house itself is very comfy. All amenities you need are there. "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (113)
"Although the bathroom is awkwardly placed in between two bedrooms (so that those in one bedroom must pass through the bathroom to get to the kitchen or to leave the apartment, which is difficult if the bathroom is being used) and there is no kitchen, there is a refrigerator, microwave, dining room table, couch with large screen television, comfy beds, closets, and an ample bathroom with a great water flow shower. Clean towels and shampoo are provided. The rental cost was quite reasonable. In...
The price is SAR 469
SAR 895 total
includes taxes & fees
9 Dec - 10 Dec
MOUNT VERNON RETREAT 🌸

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

Waterfront Home on the Chesapeake Bay!

10.0 out of 10, Exceptional, (23)
"Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small...
Waterfront Home on the Chesapeake Bay!

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (18)
"This house is absolutely fabulous! Very spacious, stocked with necessary supplies and many amenities. Beautiful property and views of the water, sunrises and sunsets. We especially liked all the wonderful decks, kitchen on the bottom level, many bathrooms, and comfortable furnishings. John and Christina were excellent host. They responded immediately to any concerns or questions. They were easy to communicate with during the check-in and check-out process. I would definitely love to...
WATERFRONT!!! The River's Roost on The Patuxent River

Secluded waterfront house to relax or enjoy water activities from private pier

9.8 out of 10, Exceptional, (25)
"Overall very pleased. Seemed like a lot of money for the property but I guess that’s what waterfront cost. House was very clean and well equipped. Loved the mini-splits in each room. The only reason I gave “cleanliness” four stars is because the outside trash can had a bunch of trash the smelled horrible and the recycling container also had trash in it. Michelle was great and very responsive. There’s a great market on the island but very few dining options and no fine dining. Very cozy...
Secluded waterfront house to relax or enjoy water activities from private pier

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

9.8 out of 10, Exceptional, (7)
"Comfortable home and a great place to get away for a chance to exhale and unwind. Host was great! Sunrises, night sky and water front makes this a wonderful relaxing getaway!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (11)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace

Blue Heron Retreat on the Water

10.0 out of 10, Exceptional, (10)
"The place was as described. Great communication and check in. All professional."
Blue Heron Retreat on the Water

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

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

9.8 out of 10, Exceptional, (35)
"The groomsmen and their families attending my daughter's nearby wedding stayed at this spectacular property. I heard nothing but high praise for its beauty, amenities, and comfort. So glad this all worked out for the dates we needed it for!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront Relaxing Getaway

9.8 out of 10, Exceptional, (18)
"Nice house, beautiful waterfront property, great host. No complaints whatsoever, highly recommend. "
Waterfront Relaxing Getaway

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (39)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

10.0 out of 10, Exceptional, (182)
"We had a very relaxing weekend celebrating my 60th birthday. Ray was such a terrific host. Everything about the property and the owner was spectacular!!"
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

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

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

BeachWalk Cottage - Charm by the Chesapeake Bay

9.8 out of 10, Exceptional, (83)
"Great for a small town, quiet, family beach vacation. "
BeachWalk Cottage - Charm by the Chesapeake Bay

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, (18)
"The property is perfect for family gatherings "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
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

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

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

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is SAR 563
SAR 1,178 total
includes taxes & fees
22 Dec - 23 Dec
Soul Oasis - home on the Chesapeake Bay
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.