St. Mary's County Holiday Rentals

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Top Cities in St. Mary's County

Top Holiday Rentals Destinations in St. Mary's County

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

10.0 out of 10, Exceptional, (116)
"It was a great stay!"
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

Tiny, Funky, and Full of Love - Welcome to the Love Shack

10.0 out of 10, Exceptional, (3)
"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

9.8 out of 10, Exceptional, (137)
"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (73)
"Absolutely perfect location to get away for the weekend. It was so peaceful and we saw osprey and deer in the back yard. You have access to a dock which is fantastic at night to see the stars. The house has everything you could need. They have 2 kayaks we intended to use but ran out of time. The best part was sitting outside at night with a fire. Would absolutely stay again! "
Waterfront Cottage in Beautiful Hoopers Island

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (50)
"Great stay and peaceful spot. "
The price is AU$319
includes taxes & fees
28 July - 29 July
Cheery, Peaceful Water Front Cabin on Winery Grounds

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (176)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Oceanfront White Stone Cottage w/ Private Beach!

7.4 out of 10, Good, (79)
"We came over and were we greeted at property that has an amazing view. The place was cozy and welcoming."
Oceanfront White Stone Cottage w/ Private Beach!

Waterfront 3-Bed Oasis Perfect for City Getaway

10.0 out of 10, Exceptional, (11)
"My family and i enjoy our stay. The lake was so beautiful"
Waterfront 3-Bed Oasis Perfect for City Getaway

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

9.6 out of 10, Exceptional, (89)
"This is a wonderful property to visit. It was in a great location with beautiful views. The property is clean, the host was friendly and accommodating. It is a location that I would definitely recommend and go back to visit again."
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

9.8 out of 10, Exceptional, (42)
"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 Solomons Apartment

9.4 out of 10, Exceptional, (9)
"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "
The price is AU$406
includes taxes & fees
11 Aug - 12 Aug
Waterfront Solomons Apartment

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (65)
"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

Spacious waterfront home with dock and sunset view

9.6 out of 10, Exceptional, (4)
"The check in process was simple and easy. The house was spacious enough for my large family. There was a dock for the boat and the swimming area was great. The kids had a blast swimming and playing on the water mat. Early mornings and evenings were peaceful as you watched some wildlife. A great time was had by everyone."
Spacious waterfront home with dock and sunset view

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is AU$459
includes taxes & fees
27 July - 28 July
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

10.0 out of 10, Exceptional, (119)
"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

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

10.0 out of 10, Exceptional, (49)
"Very clean and in a great location. Would love to stay there again. "
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

'river's Edge Retreat With Kayaks & River Access!

3.0 star property
'river's Edge Retreat With Kayaks & River Access!

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!
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 St. Mary's County Hotel Reviews