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Compare 278 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (118)
"Great location for Nationals games or DC area sight seeing. If all you need is a safe place to lay your head and not bleed out your wallet, this place is a simple, no frills to do just that. Shower was roomy with great pressure. Beds were ok. You do have to walk thru one room, then thru the bathroom, to the twin beds room but wasn’t a big deal for us and our teen boy. No kitchen sink but we didn’t eat in. That’s the beauty of a trip away. Local place for custard and food were awesome. Explored...
The price is SAR 563
SAR 1,005 total
includes taxes & fees
13 Apr - 14 Apr
MOUNT VERNON RETREAT 🌸

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (160)
"The house was awesome, the view couldn’t have been better. Loved everything about it, quiet and peaceful and it is on a dead end short road with wildlife in the yard in the morning, deer, fox, blue heron, bald eagle, geese and ducks, just fabulous. Will definitely be going back soon I hope."
Waterfront Wildlife Retreat on the Patuxent River

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (71)
"This property is lovely. So close to my daughter it’s a perfect weekend getaway. "
Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (59)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"This house was just like the listing: clean, bright, and beautiful. The beds were comfortable and the kitchen was well-appointed. Even though it rained and we couldn't use the fire pit, the bird-watching was excellent! "
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (2)
"Sweet little place on the water. Quiet neighborhood. Quick trip to campus."
Screened Patio, Deck & Grill: Saint Inigoes Home!

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Title say it all. My better half and I stayed for a weekend to change the pace. This property was ideal. Perfect location from the boardwalk and everything else we wanted to see. Anything we wanted to do that wasn't in walking distances was within a 6 minute drive. That's a solid win."
The Lazy Crab Beach House - Free beach passes

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is SAR 732
SAR 1,438 total
includes taxes & fees
8 Apr - 9 Apr
The Cottage

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...
Belle of the Chesapeake Bay

Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

9.6 out of 10, Exceptional, (24)
"The property is beautiful. The house is spacious and has comfortable beds and excellent bathrooms. There were some things that could make a stay so much better. The bedrooms need at least one chair. Although there were books in a drawer with directions for the high end appliances, each one should have a quick explanation on usage next to it. The information said the table seated 8 and yet there were only six chairs! A putting green was described and even showed a picture of one in the original...
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Cozy Cottage 3 beds 2 baths

9.8 out of 10, Exceptional, (78)
"Absolutely perfect, will stay here again and again when visting family in Maryland. "
Cozy Cottage 3 beds 2 baths

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

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"We stayed for a motorcross race (son was racing). We didnt do much at the house. Its nestled back in a quiet point on the water. Easy commute to and from to the grocery/simple shopping stores. Starbucks right down the street for you coffee lovers. The interior decor is simple and antique."
Waterfront House with Dock, Kayaks, & Sailboat!

5 bedroom, 8 bed, 3 story house a block from beach

9.6 out of 10, Exceptional, (13)
"Everything went extremely smooth. Check in was easy. House was nice and clean. Had a lot of fun with the gaming stuff they had set up! The house had everything you could imagine and more! Owners were extremely nice and informative. Recommended good places to go and eat. Overall great experience and would definitely go again."
5 bedroom, 8 bed, 3 story house a block from beach

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
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

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
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.