St. Mary's County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

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

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, (10 reviews)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is HK$1,006
HK$2,491 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Interior

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks

Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
Lexington Park
10.0 out of 10, Exceptional, (5 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,735
HK$3,317 total
includes taxes & fees
15 Mar - 16 Mar
Waterfront Escape | Family-Friendly | Remodeled Home | Epic Sunset Views | Decks
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)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
United States
Lauren A.
The price is HK$1,759
HK$4,245 total
includes taxes & fees
10 Mar - 11 Mar
Anne & Fred`s Leonardtown Home W/ Arcade room!
TV

Waterfront Retreat | Sunset Views + Outdoor Lounge

Waterfront Retreat | Sunset Views + Outdoor Lounge
Leonardtown
The price is HK$1,032
HK$2,985 total
includes taxes & fees
16 Feb - 17 Feb
Waterfront Retreat | Sunset Views + Outdoor Lounge
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, (1 review)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is HK$2,345
HK$4,480 total
includes taxes & fees
13 Feb - 14 Feb
Charming Waterfront 3-bedroom house in Piney Point
Property grounds

Come relax yourself a while

Come relax yourself a while
Mechanicsville
The price is HK$1,934
HK$4,588 total
includes taxes & fees
17 Feb - 18 Feb
Come relax yourself a while
Dining

Haven 2

Haven 2
2.5 star property
Waldorf
The price is HK$357
HK$788 total
includes taxes & fees
13 Feb - 14 Feb
Haven 2
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (41 reviews)
"The cozy cabin had everything needed for a comfortable stay. It was in a very private setting with the beach access a few houses away. You can hear the Chesapeake bay lapping at the shore and catch a glimpse of sail boats going by. We enjoyed our time at the home."
United States
Mary G.
The price is HK$1,094
HK$2,237 total
includes taxes & fees
10 Mar - 11 Mar
Soul Oasis - home on the Chesapeake Bay
Exterior

Cheery, Peaceful Water Front Cabin on Winery Grounds

Cheery, Peaceful Water Front Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (58 reviews)
"Very quiet and great location."
United States
Cindy B.
The price is HK$443
HK$1,494 total
includes taxes & fees
16 Feb - 17 Feb
Cheery, Peaceful Water Front Cabin on Winery Grounds
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,075
HK$2,481 total
includes taxes & fees
17 Feb - 18 Feb
Cottage Located on the Patuxent River!
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 HK$1,090
HK$2,034 total
includes taxes & fees
16 Feb - 17 Feb
Deal Island Bay Cottage
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 HK$922
HK$2,212 total
includes taxes & fees
5 Mar - 6 Mar
Sail Away
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$2,081
HK$2,929 total
includes taxes & fees
13 Feb - 14 Feb
Coles Point Marina
Marina

Come escape to Smith Island for the winter and enjoy nature, peace and quiet

Come escape to Smith Island for the winter and enjoy nature, peace and quiet
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"This was our first visit to Smith Island and the Double H was perfect. It was close to the ferry landing so getting there was very easy. The house was well appointed and felt like home as soon as we arrived. We enjoyed the quiet of the island and we were able to fully disconnect and relax Thank you for a great day."
United States
Amanda W.
The price is HK$1,407
HK$2,372 total
includes taxes & fees
16 Feb - 17 Feb
Come escape to Smith Island for the winter and enjoy nature, peace and quiet
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
9.2 out of 10, Wonderful, (10 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 HK$554
HK$2,452 total
includes taxes & fees
16 Feb - 17 Feb
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50 reviews)
"The house was completely spotless - the location was perfect! And the host included a s'mores kit, and baited crab traps and had them waiting with crabs in them when we arrived! This was an excellent weekend - we would recommend Hudson House to anyone!"
United States
Elizabeth G.
The price is HK$1,934
HK$3,765 total
includes taxes & fees
19 Feb - 20 Feb
Beautiful Waterfront Retreat in Cambridge!
Outdoor dining

Easthaven: Game-Theme Waterfront Retreat+Fireplace

Easthaven: Game-Theme Waterfront Retreat+Fireplace
Montross
10.0 out of 10, Exceptional, (30 reviews)
"Great spot"
United States
SHAWN W.
The price is HK$1,579
HK$3,699 total
includes taxes & fees
1 Mar - 2 Mar
Easthaven: Game-Theme Waterfront Retreat+Fireplace
Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is HK$1,618
HK$4,104 total
includes taxes & fees
15 Feb - 16 Feb
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
The price is HK$1,407
HK$2,256 total
includes taxes & fees
13 Feb - 14 Feb
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
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 HK$689
HK$1,880 total
includes taxes & fees
15 Feb - 16 Feb
Newly updated 3 bedroom cottage with Solo Stove fire pit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top St. Mary's County Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Newly remodeled rooms. Very clean. Staff was so friendly and courteous! I love the fact there are two restaurants on site. "
Kimberly 2-night trip
Posted 3 days ago
Rod 'N' Reel Resort