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Compare 284 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, (53)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (119)
"Hosts were very communicative and helpful! We could not have asked for more perfect hosts. Check in and out were very easy. Beds were all very comfortable. Everything was well-stocked. TV and Internet were great. Plenty of dishes and coffee. Rooms were tastefully decorated but toddler friendly. Location and neighborhood were great, free and easy parking. Our kiddo wants us to buy the place! We hope to stay again. We did not do the wine experience. "
The price is SAR 469
SAR 886 total
includes taxes & fees
6 May - 7 May
MOUNT VERNON RETREAT 🌸

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"We came out from Hawaii to see my Daughter and Grand Daughters.The over all experience from start to finish at the property was easy and flawless. Some days it was just my wife and I and other days it was with my grand daughters spending the night, they also enjoyed the stay. There is plenty of room. The property has an excellent view and we saw some wild life. We would stay at this property again and would highly recommend it to others.A hui hou,"until we meet again," Mark and Tamara"
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, (73)
"Needed a little quiet time, and the fresh air. Had a nice time. The house is clean,stocked with basic essentials. The beds are comfortable, that is super important to me, I also enjoyed the color choices and decorations. Tracy was prompt and thorough. I’d stay again . "
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, (60)
"My husband and I took our boys ten and twelve over easter break. The property was very private. The expansive views of the yard looking out to the bay we're beautiful. The house was really clean and nicely decorated . The master bedroom had great views and the bed was amazing. It might be to buy the mattress! We were unable to put our boat in. Due to the water levels and the sludge. But we found a boat launch only ten minutes away. All in all, if you want a very relaxing vacation, this is it....
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!

9.4 out of 10, Exceptional, (3)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Enjoyed all 6 nights in this property. Manager was very responsive to all questions about the neighborhood and property. Kitchen was well stocked with pots and pans in the yard was nice to let the dog run around. "
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 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)
"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."
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, (53)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
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

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

9.8 out of 10, Exceptional, (129)
"We had the most magical weekend stay at this charming riverfront house. The view was absolutely breathtaking—watching the last rays of sunlight from the screened porch felt like pure serenity. The home itself was spotless, cozy, and beautifully decorated in a simple, elegant way that instantly put us at ease. Every detail was thought through—from gleaming clean dishes to every kitchen gadget imaginable (yes, even a Kuraje coffee maker and a funky outdoor stove!).What truly made this stay...
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.