Holiday Rentals in St. Mary's County

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Top Cities in St. Mary's County

Piney Point, Maryland, USA The Piney Point Lighthouse in southern Maryland.
Holiday RentalsHoliday Rentals

Piney Point

Piney Point

Our top choices for St. Mary's County holiday rentals

Fridge, microwave, oven, stovetop

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is €474
includes taxes & fees
27 Apr - 28 Apr
Anne & Fred`s Leonardtown Home W/ Arcade room!
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is €370
includes taxes & fees
27 Apr - 28 Apr
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Interior

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is €334
includes taxes & fees
27 Apr - 28 Apr
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Dining

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (12 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is €383
includes taxes & fees
27 Apr - 28 Apr
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Smart TV, fireplace, ping pong, books

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Property grounds

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is €494
includes taxes & fees
27 Apr - 28 Apr
Come relax yourself a while
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is €502
includes taxes & fees
29 Apr - 30 Apr
Charming Waterfront 3-bedroom house in Piney Point
Exterior

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (61 reviews)
"Very quiet and great location."
United States
Cindy B.
The price is €222
includes taxes & fees
28 Apr - 29 Apr
Rest & Recharge, A-frame Cabin on Winery Grounds
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (46 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is €255
includes taxes & fees
4 May - 5 May
Soul Oasis - home on the Chesapeake Bay
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is €220
includes taxes & fees
28 Apr - 29 Apr
Deal Island Bay Cottage
Property grounds

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

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is €226
includes taxes & fees
27 Apr - 28 Apr
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Smart TV

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.4 out of 10, Exceptional, (12 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
The price is €272
includes taxes & fees
27 Apr - 28 Apr
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is €281
includes taxes & fees
27 Apr - 28 Apr
Walk to Beach! King Bed & Free Beach Passes
Beach

Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is €211
includes taxes & fees
3 May - 4 May
Tangier Escape, great place get away from it all on Deal Island, MD.
Marina

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is €259
includes taxes & fees
27 Apr - 28 Apr
Summer is almost here on Smith Island! Get ready for a great season on the Bay
Property grounds

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (9 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is €247
includes taxes & fees
27 Apr - 28 Apr
Sail Away
3 bedrooms, free WiFi, bed sheets

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (20 reviews)
"Great place "
United States
Myranda R.
The price is €223
includes taxes & fees
5 May - 6 May
Newly updated 3 bedroom cottage with Solo Stove fire pit
Exterior detail

The Nook in Kilmarnock Va 3 bedroom

The Nook in Kilmarnock Va 3 bedroom
Kilmarnock
10.0 out of 10, Exceptional, (3 reviews)
"Easy check in and out. Owner was helpful. House was clean and well equipped. Beds were comfortable. Location was convenient and quiet. "
United States
Margaret K.
The price is €375
includes taxes & fees
10 May - 11 May
The Nook in Kilmarnock Va 3 bedroom
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is €373
includes taxes & fees
27 Apr - 28 Apr
Coles Point Marina
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €372
includes taxes & fees
27 Apr - 28 Apr
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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

My Place Hotel - Dahlgren/King George, VA

My Place Hotel - Dahlgren/King George, VA

10/10 Excellent
"Wow! I am pleased with my rxperience here. Thst staff was friendly, the room was clean, and there little shop had all you needed for snacks and a quick bite. The hotel is next to a shopping area with a variety of stores to chekc out. I do highly recommend!"
Tiffany 1-night trip
Posted 2 hours ago
My Place Hotel - Dahlgren/King George, VA

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Holiday Homes in St. Mary's County

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