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  2. Maryland
  3. Charlestown
  4. Rentals by Owner

Discover Your Perfect Charlestown Rentals by Owner

Charlestown Rentals by Owner

More Top-Rated Rentals by Owner in Charlestown Area

Why Choose Rent By Owner for your Charlestown vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Charlestown

When should you plan your Rentals by Owner stay?

Timing your visit to this charming area can enhance your experience, so consider planning your vacation during the shoulder seasons when the region offers pleasant weather and fewer crowds, ensuring a more enjoyable stay with your preferred rental by owner.

Peak Season Highlights

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Spring (March to May)

During spring, the area comes alive with pleasant weather, making it an ideal time to enjoy outdoor activities and explore the region comfortably.

Average Temperature Daytime: 60°F to 75°F - Nighttime: 40°F to 55°F
autumn
Fall (September to November)

Autumn offers a mild climate and stunning foliage, providing a picturesque backdrop for your stay in this destination.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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Summer (June to August)

The summer months feature warmer temperatures that are perfect for enjoying outdoor recreation, although the region can be busier with visitors.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 60°F to 65°F
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Winter (December to February)

Winter tends to be quieter, offering a peaceful atmosphere if you prefer less crowded accommodations and cooler weather.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Charlestown

How to Book Your Charlestown vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Charlestown

More Top-Rated Rentals by Owner in Charlestown Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining spaces perfect for gathering with family and friends.
  • Relax in private patios or decks that offer scenic views of the surrounding area.
  • Make use of outdoor grills for a convenient barbecue experience.
  • Take advantage of expansive yards ideal for outdoor activities and games.
  • Cool off in swimming pools available at select rentals in the region.
  • Explore nearby walking trails and nature paths directly from your vacation rental.
  • Use outdoor fire pits for cozy evenings under the stars, making your stay here memorable.

Top Attractions Around Charlestown

What attractions are nearby?

In this scenic destination, you can enjoy a variety of outdoor activities and cultural experiences just moments from your rental by owner, making it an ideal base for exploring the natural beauty and local charm of the region.

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Family Activities

  • Chesapeake Harbor Marina: Spend a day exploring the scenic waterways and enjoy family-friendly boat rentals right here in the region.
  • Charity Lane Park: Relax and play at this local park featuring playgrounds, picnic areas, and open spaces perfect for family outings.
  • Historic Charlestown Museum: Dive into the area's history through engaging exhibits that educate and entertain visitors of all ages.
  • Havre de Grace Discovery Center: Discover interactive exhibits and nature programs that make exploring the natural beauty of the region fun for everyone.
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Adult Activities

  • Explore the Chesapeake Bay Maritime Museum: Gain insight into the area's rich maritime history through engaging exhibits and boat tours that highlight the region’s nautical heritage.
  • Enjoy outdoor recreation at the Charlestown Riverfront Park: Relax by the waterfront, take a leisurely walk along scenic trails, or indulge in picnicking with picturesque views of the water.
  • Visit local art galleries and studios: Discover unique works crafted by regional artists, perfect for a cultural outing that supports the area's vibrant creative community.
  • Experience the region’s outdoor nature trails: Venture into nearby parks and preserves for peaceful hikes and birdwatching opportunities amidst the region’s natural beauty.

Charlestown Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: Take time to research local events and outdoor activities available nearby to fully enjoy your stay in this charming area.
  • Choose a Rental Close to Key Attractions: Opt for properties near popular spots or scenic areas to maximize your exploration and minimize travel time.
  • Communicate Clearly with Hosts: Reach out to your rental owner ahead of time for personalized recommendations and to ensure all your needs are met during your visit.
  • Make Use of Local Resources: Utilize community guides or online reviews to discover hidden gems and authentic experiences exclusive to this destination.

Transportation Options

  • Car Rentals: You can easily rent a vehicle in the area to explore Charlestown and its surrounding attractions at your own pace.
  • Public Transit: Local bus services provide a convenient and budget-friendly way to get around this destination without the need for a car.
  • Taxi Services: Reliable taxi options are available for quick, door-to-door transportation within the region.
  • Bike Rentals: For an eco-friendly experience, consider renting a bike to enjoy the scenic views around this part of Maryland at your leisure.

Local Customs Options

  • Quaint Fishing Practices: Locals traditionally engage in fishing with specific seasonal and freshwater techniques, offering you a glimpse into the area's maritime heritage.
  • Community Celebrations: Participating in regional festivals and parades is common here, reflecting close-knit community ties and local pride.
  • Respect for the Land and Water: Visitors are encouraged to observe conservation customs that preserve the natural beauty of the region's waterways and parks.
  • Local Dining Etiquette: When exploring the area’s cuisine, it’s customary to enjoy fresh seafood dishes prepared with traditional methods cherished by residents.

Frequently Asked Questions About Charlestown Rentals by Owner

1. What are the top vacation rentals in Charlestown?

There are a lot of options in Charlestown. If you plan on staying in the Charlestown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Charlestown:

2. How many Rentbyowner vacation rentals are available in Charlestown?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 128 in the Charlestown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Charlestown. 

3. What is the cancellation policy for a rental by owner in Charlestown, Maryland?

Cancellation policies can vary depending on the individual listing. You should review the specific rental’s cancellation terms directly on the listing or contact the owner for detailed information.

4. How do I communicate with the property owner before booking my stay?

You can reach out to the owner through the messaging feature provided on the booking platform. This allows you to ask questions and clarify details before finalizing your reservation.

5. Are there any additional fees I should be aware of when booking a rental in this area?

Additional fees such as cleaning, service charges, or security deposits may apply. These are typically disclosed in the listing, so it’s best to review the details carefully or confirm with the owner.

6. What amenities are commonly available in rentals by owner in this region?

Rentals often include amenities like Wi-Fi, kitchen facilities, parking, and outdoor spaces. Check each listing for specific amenities offered to ensure they meet your needs.

7. Is there a minimum stay requirement for rentals here?

Minimum stay requirements can differ between listings. Review the specific property details or contact the owner to confirm any restrictions before booking in this part of Maryland.

More Rentals You May Like Near Charlestown

More Top-Rated Rentals by Owner in Charlestown Area