A white building with a red roof and a lighthouse tower, surrounded by tall grass and under a cloudy sky.

Holiday Rentals in St. Mary's County

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Top Cities in St. Mary's County

A lighthouse and a historic building with a porch, surrounded by a grassy area and trees.
Holiday RentalsHoliday Rentals

Piney Point

Piney Point

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

A covered patio with a view of a lake, furnished with chairs and a table.

1. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is €338
includes taxes & fees
14 Sept - 15 Sept
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is €494
includes taxes & fees
13 Sept - 14 Sept
Anne & Fred`s Leonardtown Home W/ Arcade room!
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is €390
includes taxes & fees
22 Sept - 23 Sept
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A two-story house with a balcony, surrounded by trees and a wooden fence.

4. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is €682
includes taxes & fees
14 Sept - 15 Sept
Charming Waterfront 3-bedroom house in Piney Point
A wooden cabin with a balcony, surrounded by lush greenery and trees.

5. Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (71 reviews)
"Always a great stay! "
United States
Amy H.
The price is €214
includes taxes & fees
10 Sept - 11 Sept
Rest & Recharge, A-frame Cabin on Winery Grounds
A single-story house with a front porch, a small deck, and a number '4' on the side.

6. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is €209
includes taxes & fees
5 Oct - 6 Oct
Coles Point Marina
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

7. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (7 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €227
includes taxes & fees
16 Sept - 17 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A waterfront hotel with a long pier extending into the water, a large building with multiple floors, and a clear sky.

8. Sail Away To

Sail Away To
Colonial Beach
9.6 out of 10, Exceptional, (17 reviews)
"The apartment was beautiful. he location made it easy to get around. Being able up front to the bay was awesome. Had my morning coffee on the deck."
United States
Christina
The price is €267
includes taxes & fees
30 Sept - 1 Oct
Sail Away To
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

9. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (61 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is €273
includes taxes & fees
7 Oct - 8 Oct
Soul Oasis - home on the Chesapeake Bay
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

10. 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
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is €228
includes taxes & fees
10 Sept - 11 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

11. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (55 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is €286
includes taxes & fees
10 Oct - 11 Oct
Cozy Virginia Potomac Riverfront Cottage
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

12. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is €269
includes taxes & fees
10 Sept - 11 Sept
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

13. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is €291
includes taxes & fees
13 Sept - 14 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

14. 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, (25 reviews)
"Great place "
United States
Myranda R.
The price is €217
includes taxes & fees
15 Sept - 16 Sept
Newly updated 3 bedroom cottage with Solo Stove fire pit
A lakeside view with chairs and a table, a rainbow, and trees.

15. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (23 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is €307
includes taxes & fees
10 Sept - 11 Sept
Bright and airy waterfront getaway
An aerial view of a coastal area with a sandy beach, a small settlement with houses, and a calm sea.

16. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is €411
includes taxes & fees
15 Sept - 16 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €385
includes taxes & fees
10 Sept - 11 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A sandy beach with footprints, a pier in the distance, and a clear sky.

18. 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, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is €215
includes taxes & fees
16 Sept - 17 Sept
Tangier Escape, great place get away from it all on Deal Island, MD.
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

19. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is €354
includes taxes & fees
15 Sept - 16 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A bedroom with a bed, bedside tables, a window with curtains, a patterned rug, and a ceiling vent.

20. Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (40 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is €251
includes taxes & fees
15 Sept - 16 Sept
Belle Haven - High Speed internet, walk to town
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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"Great stay! Staff was super friendly and rooms are definitely soundproof!! My super noisy 3 year old was VERY noisy and we were surprised and delighted to not be disrupting other people’s stays!!"
Bailey 2-night trip
Posted 8 hours ago
avid hotel California - Lexington Park by IHG

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Holiday Homes in St. Mary's County

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