246+ Pet Friendly Hotels and Vacation Rentals in Leonardtown |
  1. USA
  2. Maryland
  3. Leonardtown

Leonardtown Pet Friendly Vacation Rentals

About Leonardtown Vacation Rentals

There are more than 246 places to stay in Leonardtown and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Leonardtown.

Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Leonardtown, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Leonardtown. Places to stay near Leonardtown are 971.94 ft² on average, with prices averaging US $345 a night.

PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Leonardtown with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.

Show more
Show less

Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Leonardtown

Type Count
Vacation Homes 156
Cottages 29
Holiday Apartments 16
Villas 1

Use these Quick Filters to Find a Vacation Rental in Leonardtown

★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Leonardtown.

Weather in Leonardtown, MD

View the weather forecast for Leonardtown before booking your hotel or rental.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Leonardtown, MD

PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of Leonardtown's attractions.


Port of Leonardtown Winery
Patuxent River Naval Air Station
Maryland International Raceway
St. Mary's College of Maryland
Calvert Cliffs State Park
Point Lookout State Park
Westmoreland State Park
St. Mary's River State Park
Historic St. Mary's City
Budds Motorcross Speedway
Bayside Marina
Cove Point Lighthouse
Hague Winery
Running Hare Vineyard
Stratford Hall Plantation
Aqualand Marina
Warsaw Town Park
Cecil's Old Mill
Ingleside Vineyards

Other Places to Stay in Leonardtown, MD


Port of Leonardtown Winery 219 Properties
St. Mary's County 187 Properties
Compton 25 Properties

Frequently Asked Questions About Leonardtown?

What are the top vacation rentals in Leonardtown?

Find the best options in or near Leonardtown for pet-friendly travel. If you are planning a trip or vacation in Leonardtown, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Leonardtown:

How many vacation rentals have private pools in Leonardtown?

We have found 1 accommodation options with private pools in or near Leonardtown, many of which accept and welcome pets. Top-rated hotels, resorts,and places to stay that have access to a swimming pool include:

Which vacation homes in Leonardtown are best for families?

Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Leonardtown? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Leonardtown:

How many PetFriendly vacation rentals are available in Leonardtown?

PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2025 is over 246 in the Leonardtown area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Leonardtown.


People Also Ask

There are 246 Leonardtown, MD Vacation Rentals

Recently Booked Pet Friendly Hotels and Vacation Rentals in Leonardtown