31 Properties in Leonardtown, Maryland, United States of America. June 7, 2026 through June 8, 2026

Where to?

Dates

Travelers

Room 1

Adults

ChildrenAges 0 to 17

Need to book 9 or more rooms?

Sort & Filter

Compare properties

Get a side-by-side view of up to 5 properties.

Search by property name

e.g. Marriott

Filter by

Star rating

1 star

2 stars

3 stars

4 stars

5 stars

Guest rating

Making a selection from this group results in this page refreshing to show relevant results

Good 7+

Very good 8+

Wonderful 9+

Any

Traveler experience

Eco-certifications

LGBTQ welcoming

Business friendly

Family friendly

Adults only

Luxury

Wedding

Romantic

Budget

Property amenities

Pool

Pet friendly

Wifi Included

Air conditioned

Airport shuttle included

Hot tub

Spa

Washer and dryer

Kitchen

Electric car charging station

Gym

Cribs

Parking

Outdoor space

Restaurant

Indoor pool

Bed linens provided

Balcony or patio

Indoor fireplace

Grill

Kids' high chair

Heated pool

Property type

Ryokan

Residence

Lodge

Inn

Palace

Cabin

Cruise

Villa

Hotel

Bed & breakfast

Hostal

Private vacation home

Castle

Pousada (Brazil)

Country House

Motel

Holiday Park

Pension

Hostel/Backpacker accommodation

Ranch

Pousada

Guesthouse

Chalet

Camping

Riad

Houseboat

Condo resort

Farm

Safari

TownHouse

Cottage

Aparthotel

Tree house

Resort

Capsule Hotel

Apartment or condo

Boat

Property cancellation options

Fully refundable property

Meal plans available

Breakfast included

Dinner included

Lunch included

All inclusive

Payment type

Pay over time with Affirm

Reserve now, pay later

Accessibility

In-room accessibility

Elevator

Accessible bathroom

Wheelchair accessible parking

Roll-in shower

Stair-free path to entrance

Service animals allowed

Sign language-capable staff

Accessible pool

Handrail in stairway or hallway

Single-level property

Entrance ramp

Accessible path of travel

Accessible van parking

One Key benefits and discounts

Member Prices

VIP Access properties

Top-rated stays with member perks

Discounted properties

Major discounts on selected stays

Room views

Ocean view

Lagoon view

Pool view

City view

Canal view

Bay view

Valley view

Resort view

Hill view

Water view

Marina view

Vineyard view

Courtyard view

River view

Mountain view

Golf course view

Desert view

Park view

Garden view

Lake view

Harbor view

Number of bedrooms

Studio

Popular filters

Popular

Room amenities

Porch or lanai

Private bathroom

Blackout curtains

Air conditioning

Accessibility features

Top floor

Private hot tub

Jetted or soaking bathtub

In-room entertainment

Yard

Personal safe

Fireplace

WiFi

Refrigerator

Coffee/tea maker

Private sauna

Swim-up room

Kitchen or kitchenette

Private pool

Ground floor

Balcony or patio

Iron and board

Microwave

Oven

Dishwasher

Beach access

On the beach

Nothing between you and the sand

Near the beach

Stays within a 15-minute walk to the beach

Total price

Min

Max

$0, Minimum, Total price

$1,000 and above, Maximum, Total price

Availability

Only show available properties

Popular locations

Making a selection from this group results in this page refreshing to show relevant results

St. Mary's River State Park

New Towne Neck State Park

Port of Leonardtown Winery

The Shoppes at McIntosh

Saint Mary's Fairground

Leonardtown Park

Indian Village Archeological Park

Sandyland Beach

Leonard's Grant Community Area

Miedzinski Park

College of Southern Maryland - Leonardtown Campus

Leonardtown Library

Salem State Forest

Leonard's Grant Recreation Area

Abell's Wharf

Saint Mary's County Library Leonardtown Branch

Breton Bay Golf Course

MedStar Saint Mary's Hospital

Leonardtown Town Hall

Neighborhood

Making a selection from this group results in this page refreshing to show relevant results

Leonardtown

Property brand

Holiday Inn Express

TravelStaytion

Hampton Inn

My Place Hotels

Comfort

Country Inn & Suites - by Choice Hotels

Ascend Collection

Extended Stay America Suites

Hilton Garden Inn

Fairfield Inn and Suites

La Quinta Inn & Suites

Quality

Super 8

Sleep Inn

avid hotels

Red Roof Inn

SureStay

TownePlace Suites

Home2 Suites by Hilton

Spark by Hilton

SpringHill Suites

Nearby activities

Museums

Golfing

Rock or mountain climbing

Spa and wellness

Cycling

Wineries or breweries

Theme parks

Skiing or snowboarding

Winter activities

Enjoy the season with activities like ice skating, snowmobiling, or sledding.

Scuba diving or snorkeling

Fishing

Zoo or wildlife viewing

Horseback riding

Hiking

Shopping

Watersports

Tennis

Casino

All stays

Hotels

Homes

31 properties

How our sort order works

Search results

A modern kitchen with white cabinets, a central island with bar stools, stainless steel appliances, and a large window with blinds.

A two-story house with a balcony, surrounded by trees and a wooden fence.

Charming Waterfront 3-bedroom house in Piney Point

Entire home by Vrbo

Sleeps 8 · 3 bedrooms · 3.5 bathrooms

Dog-friendly

Balcony

Dog-friendly, Balcony, AC

1010 out of 10

Exceptionalexceptional

6 reviews(6 reviews)

$364 nightly

The current price is $823 total

$823 total

Total with taxes and fees

More information about Charming Waterfront 3-bedroom house in Piney Point, opens in a new tab

A room with a large window overlooking a lake, framed by a white window sill and a wooden table with a vase of flowers.

A wooden double door with glass panels, a porch with a railing, and a view of the outdoors.

Swanendele Inn at St. Mary's Maryland

Outdoor seats

Private beach

Breakfast incl

Outdoor seats, Private beach, Breakfast incl

9.89.8 out of 10

Exceptionalexceptional

34 reviews(34 reviews)

$625 nightly

The current price is $694 total

$694 total

Total with taxes and fees

We have 1 left at this price

More information about Swanendele Inn at St. Mary's Maryland, opens in a new tab

A beach with a wooden pier extending into the water, a picnic table, and a clear sky.

A single-story house with a front porch, a small deck, and a number '4' on the side.

Coles Point Marina

Pet for a fee

Private beach

Parking incl

Pet for a fee, Private beach, Parking incl

$335 nightly

The current price is $457 total

$457 total

Total with taxes and fees

We have 2 left at this price

More information about Coles Point Marina, opens in a new tab

Sort & Filter

Search by property name

Filter by

Star rating

Guest rating

Traveler experience

Property amenities

Property type

Property cancellation options

Meal plans available

Payment type

Accessibility

One Key benefits and discounts

Room views

Number of bedrooms

Popular filters

Room amenities

Beach access

Total price

Availability

Popular locations

Neighborhood

Property brand

Nearby activities

Search results

Photo gallery for Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point

Photo gallery for Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

Photo gallery for Coles Point Marina

Coles Point Marina