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  3. Chestertown
  4. Rentals by Owner

Discover Your Perfect Chestertown Rentals by Owner

Chestertown Rentals by Owner

More Top-Rated Rentals by Owner in Chestertown Area

Why Choose Rent By Owner for your Chestertown 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 Chestertown

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider visiting during the local shoulder seasons when the region offers pleasant weather and fewer crowds, ensuring your rental experience here is both enjoyable and relaxed.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, the area offers mild temperatures and longer daylight hours, making it ideal for exploring and enjoying outdoor activities.

Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
autumn
Early Fall (September to October)

This period features comfortable weather with fewer crowds, providing a peaceful setting to experience the region’s natural beauty.

Average Temperature Daytime: 68-75°F - Nighttime: 50-60°F

Off-Season Highlights

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Winter (December to February)

The winter months bring cooler temperatures, offering a quieter atmosphere for those seeking a more relaxed and intimate getaway.

Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
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Early Spring (March to April)

As the region transitions from winter, you can enjoy fewer visitors and expect serene surroundings before the peak season begins.

Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F

Weekly Weather Forecast for Chestertown

How to Book Your Chestertown 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 Chestertown

More Top-Rated Rentals by Owner in Chestertown 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

  • You can enjoy a spacious outdoor patio or deck, perfect for relaxing and entertaining amidst the natural beauty of the area.
  • Many rentals feature access to private or shared gardens, offering a serene spot to unwind or dine outdoors.
  • Expect well-maintained lawns or green spaces where you can engage in outdoor games or simply enjoy the fresh air.
  • Some properties provide outdoor dining setups, such as picnic tables or grills, ideal for enjoying meals al fresco.
  • Look for accommodations with scenic views of the nearby waterways or countryside, enhancing your outdoor experience.
  • Outdoor fire pits are commonly available, allowing you to gather and enjoy the ambiance during cooler evenings.
  • There may be opportunities to access docks or waterfront areas if your rental is close to the water, perfect for boating or fishing activities.

Top Attractions Around Chestertown

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities and local events that showcase the area's natural beauty and vibrant community spirit, making it an ideal destination for your next getaway booked through Rent By Owner in Chestertown, Maryland.

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Family Activities

  • Waterfront Park: Enjoy a family picnic and outdoor playtime at this scenic park with beautiful views along the Chesapeake Bay.
  • Kent County History Museum: Explore local history and engage your kids with interactive exhibits that bring the area's past to life.
  • Chester River: Spend a relaxing day paddleboarding or kayaking on the tranquil waters, perfect for outdoor family adventures.
  • Chestertown Marina: Take a boat tour or rent a watercraft to explore the region’s waterways and create memorable family moments.
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Adult Activities

  • Historic Downtown Exploration: Stroll through charming streets filled with boutique shops, historic architecture, and inviting cafes that showcase the area's rich heritage.
  • Boating and Water Activities: Enjoy canoeing, kayaking, or sailing on the scenic Chester River, offering a relaxing way to experience the region's natural beauty.
  • Gourmet Dining Experiences: Savor local cuisine at waterfront restaurants that highlight fresh seafood and regional flavors in a welcoming setting.
  • Art Galleries and Cultural Events: Discover contemporary art, attend live performances, or participate in local festivals that celebrate the region’s vibrant arts scene.

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Chestertown Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local events and markets: Engaging with the community’s happenings enhances your experience by immersing you in the area's vibrant culture and lifestyle.
  • Choose a waterfront rental: Opting for accommodations near the water provides scenic views and easy access to the region's natural beauty and outdoor activities.
  • Plan your outdoor adventures: Take advantage of nearby parks and nature spots to enjoy the region's tranquil landscapes and outdoor recreation opportunities.
  • Coordinate with your host prior to arrival: Communicating with your rental owner ensures a smooth check-in process and personalized tips for experiencing this charming destination fully.

Transportation Options

  • Drive or Shuttle Services: You can opt for car rentals or shuttle services that provide convenient transportation around the charming area, making it easy to explore local attractions and amenities.
  • Public Transit: The regional bus systems connect various parts of the region, offering an economical way to get around during your stay here.
  • Taxi and Rideshare: Taxis and rideshare options like Uber and Lyft are readily available, providing flexible transportation solutions within this destination and beyond.
  • Biking and Walking: The area features scenic routes ideal for biking or walking, allowing you to enjoy the peaceful landscape while easily reaching nearby points of interest.

Local Customs Options

  • Southern Hospitality:** Visitors often notice the welcoming attitude and polite manners that reflect the area's friendly community spirit.
  • Local Festivals:** Participating in seasonal events and parades allows you to experience the area’s vibrant cultural celebrations firsthand.
  • Historic Reverence:** Respect for the area's history is observed through preservation of landmarks and adherence to traditional customs during community gatherings.

Frequently Asked Questions About Chestertown Rentals by Owner

1. What are the top vacation rentals in Chestertown?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 51 in the Chestertown 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 Chestertown. 

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

Cancellation policies vary depending on the individual listing. It is important to review the specific terms provided by the owner at the time of booking or contact them directly for detailed information.

4. Are pets allowed in rental properties in this area?

Pet policies differ among rentals in the region. To ensure your furry friend is welcome, please check the pet policy outlined in the listing or reach out to the owner for clarification.

5. How do I confirm availability and secure my booking in this destination?

Availability can be verified through the listing calendar on the platform. Once you find an available property that suits your needs, follow the booking process or contact the owner for assistance to finalize your reservation.

6. What amenities are typically included in rentals here?

Amenities vary from property to property, but common features include Wi-Fi, fully equipped kitchens, and outdoor spaces. Detailed descriptions of included amenities are available in each listing, so review them carefully before booking.

7. Is there a minimum stay requirement when booking a rental by owner in this region?

Minimum stay requirements depend on the individual property owner. These details are usually specified in the listing, or you can inquire directly with the owner to confirm the length of stay needed.

More Rentals You May Like Near Chestertown

More Top-Rated Rentals by Owner in Chestertown Area