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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 225 Vacation Homes in Southern Maryland with updated reviews, rates, and availability.

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, (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
Screened Patio, Deck & Grill: Saint Inigoes Home!
Saint Inigoes Vacation Rental | 3BR | 2BA | 3 Steps to Enter | 1,456 Sq Ft

Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
The driveway allows for plenty of parking for guests!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Terrace/patio

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (69)
"Property provides relaxation and entertainment for all ages. If you can think of it, it's already there. Clean, well-kept everything in working order. Will definitely consider a longer stay in the future. Thank you for this opportunity. "
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Private kitchen

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (5)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
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
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
The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"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
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, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
The Cottage
Private kitchen

The Cottage

10.0 out of 10, Exceptional, (2)
"Couldn’t have asked for better- I appreciate the communication and willingness to work with us on a quick turn around trip. Clean. Easy to get to. Accurate description. Quiet neighborhood. 10/10 would stay again. "
The price is AED 845
AED 1,566 total
includes taxes & fees
16 Feb - 17 Feb
The Cottage
Belle of the Chesapeake Bay
Beach

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
4-BR Unique Waterfront House - Your Perfect Escape
Exterior

4-BR Unique Waterfront House - Your Perfect Escape

2.0 star property
10.0 out of 10, Exceptional, (1)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
The price is AED 826
AED 1,853 total
includes taxes & fees
16 Feb - 17 Feb
4-BR Unique Waterfront House - Your Perfect Escape
Spectacular Waterfront Retreat with Pier

Spectacular Waterfront Retreat with Pier

10.0 out of 10, Exceptional, (7)
"Classic cottage, very clean and well-supplied. Comfy bed in main bedroom! Beautiful property on the river - quiet and peaceful. Lovely sitting areas both inside and out. Restorative!"
Spectacular Waterfront Retreat with Pier
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

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

10.0 out of 10, Exceptional, (112)
"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
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Living area

2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

10.0 out of 10, Exceptional, (2)
"Quite and friendly neighbors "
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Water-View Deale Home: Walk to Marina, Restaurants
Deale Vacation Rental | 5BR | 3.5BA | 2,500 Sq Ft | Stairs Required

Water-View Deale Home: Walk to Marina, Restaurants

2.0 star property
Water-View Deale Home: Walk to Marina, Restaurants
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Ariel view of the house, dock and beautiful Chesapeake Bay.

Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths

9.0 out of 10, Wonderful, (14)
"My family enjoyed our stay over Thanksgiving. Three generations with different needs and the house accommodated us well."
Serenity Bay-Relaxing, Spacious House-Private Pool-6 bdrms-5baths
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Exterior

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (24)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AED 710
AED 1,920 total
includes taxes & fees
3 Mar - 4 Mar
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Your private beach retreat in historic St. Mary's
Welcome to your private beach and pier!

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at this property. The house was in mint condition and had all the amenities we needed. Enjoyed the hot tub, kayaks, the fire pit, and the dock. Great place to spend a relaxing long weekend. "
Your private beach retreat in historic St. Mary's
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

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

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

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is AED 474
AED 1,043 total
includes taxes & fees
17 Feb - 18 Feb
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.