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Compare 266 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
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 🌸
Living area
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 AED 459
AED 867 total
includes taxes & fees
12 Nov - 13 Nov
MOUNT VERNON RETREAT 🌸
Bay views with kayaks, bikes, fire pit, crabbing and more
Living room with tv and gas fireplace
Bay views with kayaks, bikes, fire pit, crabbing and more
9.4 out of 10, Exceptional, (16)
"We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon."
Bay views with kayaks, bikes, fire pit, crabbing and more
Waterfront Home on the Chesapeake Bay!
Private Pier
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
Property grounds
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
backyard and pier
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!
Scotland Vacation Rental | 3BR | 2BA | Stairs Required | 1,644 Sq Ft
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
California Vacation Rental | 5BR | 2.5BA | 2,300 Sq Ft | Stairs Required
Riverside House w/ Kayaks, Piano & Fireplace
8.8 out of 10, Excellent, (10)
"Clean property and just what we needed to gather with family nearby"
Riverside House w/ Kayaks, Piano & Fireplace
Blue Heron Retreat on the Water
Private dock for kayaking , swimming , boating , fishing, and even crabbing
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
Exterior
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
Exterior
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (34)
"Family stayed for my 50th birthday over a long weekend. Amazing property. Beautiful view and amazing amenities with hosts who are flexible. We had a small issue with the alarm system that we finally resolved. Will definitely book again."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront Relaxing Getaway
Property grounds
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
Exterior
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (38)
"Our daughter and her family live in Lexington Park so we visit the area often. The hotels close by don’t offer great options for a family of four with a teenage boy and a 9 year old girl, so we started looking for VRBO houses. So glad we found this gem! Sure, it’s a bit further away from our daughter (20 min instead of 10 min), but the extra space is well worth it. We loved the electric fire place and the wrap around deck was very nice. The house has everything you need and Sara was extremely...
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Exterior
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (181)
"From the listing to the greeting. It was terrific. The view was amazing, the house was great. There were a few too many bugs, dead and alive, but some bug spray could take care of.. We're planning another visit.cisit.Ithat."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
MD/VA/DC. Smallwood State Park
Exterior
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
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
Mid-Century Modern and Marvelous on the Bay
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Lusby Vacation Rental | 4BR | 3BA | 1,872 Sq Ft | Stairs Required
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
9.8 out of 10, Exceptional, (10)
"We stayed for a quick weekend during a celebration of life. We enjoyed the ample communal space. Our only complaint was the lack of dog friendly space for potty breaks and there were quite a few things with notes that were broken around the house. "
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
BeachWalk Cottage - Charm by the Chesapeake Bay
Home Front- BEACKWALK COTTAGE Wrap around porch
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!
WELCOME FRIENDS TO— “THE NORMANDY COTTAGE
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
9.6 out of 10, Exceptional, (39)
"I was very impressed with this property. It's a cute little house that was comfortable for our group of 6. It was at a great location, too. The owner was quick to respond to my questions. If we visit North Beach again, I will definitely book here again."
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
Sit on the patio and enjoy your coffee in the morning.
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

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Exterior
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
10.0 out of 10, Exceptional, (181)
"From the listing to the greeting. It was terrific. The view was amazing, the house was great. There were a few too many bugs, dead and alive, but some bug spray could take care of.. We're planning another visit.cisit.Ithat."
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
Waterfront Scotland Beach Retreat w/ Private Beach
Ridge Vacation Rental | 4BR | 4.5BA | 3,000 Sq Ft | 5 Steps Required to Access
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
Mid-Century Modern and Marvelous on the Bay
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (68)
"The ratings were Exceptional, so I was skeptical. However, it was beyond exceptional. The most well equipped rental we have seen. Great location. Well stocked. Excellent communication with the host. Couldn’t have asked for anything more. Definitely recommend, and will stay here again when in the area. We had a great time."
Mid-Century Modern and Marvelous on the 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.