Search Vacation Homes in Southern Maryland

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 284 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
MOUNT VERNON RETREAT 🌸
Aerial view

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (121)
"Nice apartment in a great location (just 10’ walk from our grandchildren. Great host, comfortable furnishings. Our grand kids had a sleepover and loved it!"
The price is AED 569
AED 1,021 total
includes taxes & fees
14 May - 15 May
MOUNT VERNON RETREAT 🌸
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (161)
"Clean and nice location. Worked perfectly for our visit to the area to spend time with our daughter, son-in-law, and two perfect grandsons. Thank you for sharing your beautiful home and location. "
Waterfront Wildlife Retreat on the Patuxent River
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop

Sweet Bamboo Beach Cottage

10.0 out of 10, Exceptional, (74)
"This house was the perfect place to visit old friends. Beds were comfortable, house had everything I needed for a long weekend, and the neighborhood was quiet and friendly. It is walking distance (a few blocks) to the boardwalk and restaurants. "
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
View from property

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Great house, great location and great host!"
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Terrace/patio

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

9.8 out of 10, Exceptional, (60)
"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
On the beach

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

10.0 out of 10, Exceptional, (114)
"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

10.0 out of 10, Exceptional, (12)
"The home is absolutely beautiful and Dina is a great host. My family and I have full intentions of coming back!"
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

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
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (48)
"Would stay again."
The Lazy Crab Beach House - Free beach passes
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The Cottage
Belle of the Chesapeake Bay
Beach

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (24)
"Great location and house! We all had a great time!"
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
Newly Renovated River Retreat w/Dock and Pool
Terrace/patio

Newly Renovated River Retreat w/Dock and Pool

Newly Renovated River Retreat w/Dock and Pool
Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite
Exterior

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite

Club Wyndham National Harbor, Maryland, 1 Bedroom Deluxe Suite
Cozy Cottage 3 beds 2 baths
Outdoor dining

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
Outdoor dining

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!
Interior

Waterfront House with Dock, Kayaks, & Sailboat!

9.0 out of 10, Wonderful, (30)
"Great location to downtown Solomons Island Center."
Waterfront House with Dock, Kayaks, & Sailboat!
5 bedroom, 8 bed, 3 story house a block from beach
Beach

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
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

Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

10.0 out of 10, Exceptional, (22)
"Perfect family get away with a great view!"
The price is AED 511
AED 1,094 total
includes taxes & fees
11 May - 12 May
Soul Oasis - home on the Chesapeake Bay
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"
The Blue Crab Beach House - Free beach passes
Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

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

9.2 out of 10, Wonderful, (20)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of 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.