Vacation Rentals in St. Mary's County

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Vacation Rentals in St. Mary's County

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

9.8 out of 10, Exceptional, (9)
"This was the perfect spot for my husband and I and our two dogs. The large fenced yard was great to spend time in. The bed and pillows were extremely comfortable. We will definitely be back if we are in the area again! "
Tiny, Funky, and Full of Love - Welcome to the Love Shack

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

10.0 out of 10, Exceptional, (124)
"Really enjoyed our time here. The outdoor space in the back was great with the swing and the fire pits. Our kids loved walking to the beach everyday and catching crabs. "
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

El Camino

10.0 out of 10, Exceptional, (49)
"Great location, the dock is perfect for sunsets, nice balance of waterfront but also cabin vibes"
El Camino

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

9.8 out of 10, Exceptional, (76)
"What a great property, wildlife abounds!!! We had a fantastic weekend with family and friends!"
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Private Beach Front Getaway at The Sunshine Beach Cottage.

9.8 out of 10, Exceptional, (76)
"We had a lovely stay at the Sunshine Beach Cottage - it was just as we expected and easy to check in and out. We look forward to the next time we can stay! "
Private Beach Front Getaway at The Sunshine Beach Cottage.

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (53)
"Great spot for a family of 4. Very quiet and clean."
The price is ¥11,361
¥32,310 total
includes taxes & fees
Oct 13 - Oct 14
Cheery, Peaceful Water Front Cabin on Winery Grounds

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

9.8 out of 10, Exceptional, (47)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Waterfront with spectacular view, close to restaurants and bars

9.8 out of 10, Exceptional, (54)
"We enjoyed our stay here! The place was incredibly clean and the view was perfect! "
Waterfront with spectacular view, close to restaurants and bars

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

10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

9.8 out of 10, Exceptional, (151)
"The place was great, the host was great,"
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

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

9.6 out of 10, Exceptional, (95)
"We had a nice quiet week in this adorable and clean home just relaxing in the pool and spending time in the kayaks. We ventured out for some yummy Mexican food for dinner, ice cream in Reedville, and the nearby cafe to try their cappuccino and breakfasts but otherwise spent a nice family week playing games and swimming. "
Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (259)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Waterfront Loft on the Yeocomico River - Kayaks, Dock & Screened Porch

10.0 out of 10, Exceptional, (3)
"Our stay was absolutely perfect. It was just what we needed a place by the water saturated with nature and wildlife. It was the perfect quiet getaway, Bill and Caren are wonderful host filled with plenty of hospitality. Thank you."
Waterfront Loft on the Yeocomico River - Kayaks, Dock & Screened Porch

Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

2.0 star property
8.0 out of 10, Very Good, (5)
"Really nice area. I will be returning. Very nice. Thank you!"
The price is ¥14,878
¥31,283 total
includes taxes & fees
Oct 19 - Oct 20
Charming 3-bedroom house with WiFi, AC& heat in peaceful Reedville

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

10.0 out of 10, Exceptional, (56)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is ¥18,259
¥37,992 total
includes taxes & fees
Oct 9 - Oct 10
Waterfront Solomons Apartment

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

9.0 out of 10, Wonderful, (29)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (80)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island
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.
Save an average of 15% on thousands of hotels when you're signed in

Top St. Mary's County Hotel Reviews

Find out more about St. Mary's County

Find out more about St. Mary's County

Vacation Apartments in St. Mary's County

Search for Vacation rentals in St. Mary's County on Expedia! You can easily find your home rentals, villas, Vacation apartments in St. Mary's County using one of the methods below:

  • View our selection of featured Vacation rentals in St. Mary's County
  • Use the map to find apartments and other Vacation homes in the St. Mary's County neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in St. Mary's County while they last

Look no further and take a look at our great range of rental properties in St. Mary's County!

Explore a world of travel with Expedia