The Islands Advisors - Vacation Rentals in Leonardtown

Blue Heron Inn - A Bed and Breakfast LLC From US $229
         

9.0 (14 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Charming 2-bedroom Cap Cod style cottage From US $185
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Enjoy Summer Days and Starry Nights on Charleston Creek! From US $234
         

9.8 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Montross Home w/Private Boat Slip! From US $212
         

House Right on the Potomac River - Great Sunrises & Sunsets From US $488
         

10.0 (100 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Leonardtown

Over 250+ Luxury Places to Stay in or Near Leonardtown
Resort Style Country Living on the Patuxent River From US $1,778
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Charleston Colonial From US $1,078
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Beach Club: your own private "Caribbean" resort From US $897
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Leonardtown

Over 41+ Top-Rated Vacation Rentals with a Pool in or Near Leonardtown
Quaint waterfront home with private beach From US $255
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Leonardtown

Over 95+ Pet-Friendly Vacation Rentals in or Near Leonardtown
2 Acre Oasis with Private Beach! Family and dog friendly! From US $638
         

10.0 (58 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Dock and Yard Hague Hideaway on the Potomac From US $266
         

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent From US $104
         

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7.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Xmas Sale! Game Theme+Boats+Beach+King Bd+EV Chrgr From US $460
         

10.0 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Relaxing Getaway From US $215
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Autumn River Haven — Firepit, Hot Tub & Views From US $226
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Leonardtown

Over 53+ Large Vacation Homes & Villas in or Near Leonardtown
Perfect Pointe, Cobb Island, Maryland From US $428
         

10.0 (56 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
The Rivers Roost Home on Patuxent River! From US $271
         

WATERFRONT! The River's Roost on The Patuxent River From US $307
         

Stunning Riverfront Property - New Listing From US $746
         

10.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Getaway at Four Waters Estate! From US $591
         

10.0 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
4-BR Waterfront Turret Home From US $435
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Leonardtown

Over 31+ Wheelchair Accessible Vacation Homes in or Near Leonardtown
Waterfront River View Home with pier and beach! From US $313
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace
Solomons Victorian Inn From US $125
         

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9.8 (29 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
avid hotel California Lexington Park by IHG From US $126
         

9.3 (3 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Inn at Leonardtown, an Ascend Collection Hotel From US $136
         

9.1 (116 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Leonardtown Varoom and Airbnb Places to Stay Under $200

Over 67+ Leonardtown Varoom and Airbnb Places to Stay Under $200
Stunning sunsets Leonardtown apartment From US $168
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern Solomons Cottage Rental - Walk to Island! From US $166
         

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10.0 (4 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
avid hotel California - Lexington Park by IHG From US $122
         

9.8 (6 Reviews)
Hotel
  • Parking
  • Business Services
  • Wellness Facilities
Shewell's A-Frame on Mill Creek From US $165
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront at the Pines of Canoe Neck From US $161
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Private Dock & Yard: Hague Hideaway on the Potomac From US $148
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Riverfront Home with dock From US $169
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Charming 2-bedroom Cap Cod style cottage From US $181
         

10.0 (1 Review)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Leonardtown

Over 109+ Instantly Bookable Vacation Homes in or Near Leonardtown
Luxury estate with jacuzzi and private pier From US $524
         

10.0 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Blue Heron Retreat on the Water From US $412
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Two bedroom two bath home on charming Solomons Island From US $349
         

10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Solomons Island with views of harbor! From US $216
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Modern Solomons Cottage Rental - Walk to Island! From US $245
         

10.0 (10 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Private Waterfront Home with Dock in Solomons, MD From US $263
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Leonardtown Vacation Rentals

With more than 259 Leonardtown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Theislandsadvisors and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Leonardtown.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Theislandsadvisors Leonardtown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Leonardtown. Places to stay near Leonardtown are 939.91 ft² on average, with prices averaging $336 a night.

Theislandsadvisors makes it easy and safe to find and compare vacation rentals in Leonardtown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Leonardtown

Type Count
Vacation Homes 168
Hotels with Suites 32
Cottages 29
Holiday Apartments 18
B&B 4
Cabin Rentals 3
Others 2
Villas 1

Use these Quick Filters to Find a Vacation Rental in Leonardtown

Pro Tip: Theislandsadvisors makes it easy to compare the best listings on Theislandsadvisors homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Theislandsadvisors homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Leonardtown.

Weather in Leonardtown

View the weather forecast for Leonardtown before booking your Leonardtown Vacation Rentals to confirm your best time to go.

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