Holiday Homes in Southern Maryland

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
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5 Sept - 7 Sept
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19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in Southern Maryland and around

Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (50)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Rising Sun Bay View Cottage
Terrace/patio

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
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, (46)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Bay views with kayaks, bikes, fire pit, crabbing and more
Fridge, microwave, oven, stovetop

Bay views with kayaks, bikes, fire pit, crabbing and more

9.6 out of 10, Exceptional, (21)
"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
The Blue Crab Beach House - Free beach passes
Beach nearby, sun-loungers, beach towels

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes
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, (121)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront Wildlife Retreat on the Patuxent River
Interior

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "
Waterfront Wildlife Retreat on the Patuxent River
MOUNT VERNON RETREAT 🌸
Outdoor dining

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (125)
"This was a lovely property and in a great location! The owners were easy to work to with and made us feel very welcome. "
MOUNT VERNON RETREAT 🌸
WATERFRONT!!! The River's Roost on The Patuxent River
Fridge, microwave, oven, stovetop

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (28)
"We had an amazing stay in this beautiful house! Inside was massive perfectly set up for our needs. Outside had stunning views and there is nothing better than being on the waters edge. The owners were easy to communicate with and they had everything ready in a timely manner for our check in. We didn’t get a chance to catch any crabs but we will definitely stay here again to try our hand at that."
WATERFRONT!!! The River's Roost on The Patuxent River
Secluded River Front Cottage
Interior

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"Nice property, with an amazing kitchen. There are beautiful sunsets and peaceful views of the water. A pleasent weekend get away"
Secluded River Front Cottage
Gorgeous 5BR/3BA Family Home in Maryland!
Terrace/patio

Gorgeous 5BR/3BA Family Home in Maryland!

2.0 out of 10, (1)
"We left immediately. Heavy use of cleaning chemicals masked an underlying problem with dust/mildew/mold. Our children complained of scratchy throats in first 30 minutes, we noticed it ourselves after an hour. Trash all over grounds as well as a general unkempt property, pictures show what we cleaned up for them before leaving. Mail overflowing mailbox. Should not be listed again without major modifications."
Gorgeous 5BR/3BA Family Home in Maryland!
Bright and airy waterfront getaway
On the beach, sun-loungers

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (16)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway
Screened Patio, Deck & Grill: Saint Inigoes Home!
Outdoor dining

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.0 out of 10, Wonderful, (8)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!
The Lazy Crab Beach House - Free beach passes
Exterior

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"Great stay"
The Lazy Crab Beach House - Free beach passes
Discover tranquility near Calvert Cliffs
Outdoor dining

Discover tranquility near Calvert Cliffs

9.8 out of 10, Exceptional, (16)
"Comfortable beds, large house with awesome views…had a great experience"
Discover tranquility near Calvert Cliffs
Walk to Beach: Elegant Escape in Lusby!
Fridge, microwave, stovetop, dishwasher

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!
Wooded Hillside Retreat in Waldorf, MD - Top 10% and Guest favorite elsewhere
Property grounds

Wooded Hillside Retreat in Waldorf, MD - Top 10% and Guest favorite elsewhere

2.0 star property
10.0 out of 10, Exceptional, (5)
"This place has been great! Owners are very communicative and helpful. We have enjoyed this house and would love to return."
Wooded Hillside Retreat in Waldorf, MD - Top 10% and Guest favorite elsewhere
Stunning secluded Luxury waterfront cottage with private deep water pier!
Exterior

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (79)
"This property was exactly as described. The owner was very easy to work with. Unfortunately, we did not get to use the fire pit as it was rainy and cold. I would 100% stay here again."
Stunning secluded Luxury waterfront cottage with private deep water pier!
Private Waterfront Home with Dock in Solomons, MD
Fridge, microwave, oven, stovetop

Private Waterfront Home with Dock in Solomons, MD

10.0 out of 10, Exceptional, (6)
"Nice and cozy"
Private Waterfront Home with Dock in Solomons, MD
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (11)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
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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Top Southern Maryland Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Location"
Elias 2-night trip
Posted 2 days ago
Rod 'N' Reel Resort