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  3. Preston
  4. Rentals by Owner

Discover Your Perfect Preston Rentals by Owner

Preston Rentals by Owner

6.6 (50 Reviews)
Cabin
Econo Lodge Easton Route 50
  • Air Conditioner
  • Parking
  • Security/Safety
View Availability
10.0 (28 Reviews)
House
Eastern Shore Oasis!
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Preston Area

Why Choose Rent By Owner for your Preston 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 Preston

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, so consider visiting during the region’s optimal seasons to enjoy pleasant weather and local events while planning your rental by owner through Rent By Owner for a seamless and trustworthy stay.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this region experiences warm weather ideal for outdoor activities and enjoying your stay in Preston. The area sees increased demand from travelers seeking a sunny getaway.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

Fall offers pleasant temperatures and vibrant foliage, making it a popular time to visit. Travelers booking through Rent By Owner can enjoy the scenic beauty of this destination during these months.

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

Off-Season Highlights

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Winter (December to February)

Winter tends to be colder and quieter, providing a peaceful retreat for those seeking solitude or off-season rates. It’s an ideal time for travelers interested in a cozy stay away from the crowds.

Average Temperature Daytime: 45°F - Nighttime: 30°F
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Early Spring (March to May)

Early spring sees fewer visitors, offering more secluded accommodations at attractive prices. It's perfect for nature lovers looking to explore as the region begins to awaken from winter dormancy.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Preston

How to Book Your Preston 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 Preston

More Top-Rated Rentals by Owner in Preston 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 seating areas perfect for relaxing and dining al fresco.
  • Take advantage of spacious yards ideal for outdoor activities or gatherings.
  • Make the most of private patios or decks that offer scenic views of the surrounding region.
  • Utilize well-maintained community gardens or green spaces nearby.
  • Access to outdoor grills for delicious barbecues during your stay here.
  • Benefit from peaceful outdoor fire pits, perfect for evening relaxation.
  • Explore nearby walking or biking trails that showcase the natural beauty of the area.

Top Attractions Around Preston

What attractions are nearby?

Enjoy a variety of outdoor activities nearby, including boating, fishing, and exploring scenic nature trails in the area, making it an ideal destination for those seeking relaxing and adventurous experiences close to your rental by owner.

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Family Activities

  • Green Harbor Nature Reserve: Explore the scenic trails and observe local wildlife at this family-friendly natural spot near Preston.
  • Chesapeake Bay Maritime Museum: Discover maritime history and enjoy hands-on exhibits that engage children and adults alike in the region's coastal heritage.
  • Preston Historical Society & Museum: Dive into the area's past through engaging exhibits and guided tours perfect for curious young explorers.
  • Local Family Farms: Visit nearby farms offering interactive activities and tasting opportunities, ideal for a fun day out in the region.
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Adult Activities

  • Chesapeake Bay Sailing Tours: Experience the region's maritime heritage with sailing excursions that offer breathtaking views and a serene escape on the water.
  • Relax at the Chesapeake Bay Environmental Center: Explore wetlands, observe diverse wildlife, and enjoy peaceful nature walks in this protected area near the region.
  • Visit the local wineries and breweries: Discover the area's vibrant wine and craft beer scene through guided tastings and tours that highlight regional flavors.
  • Golf at nearby courses: Play a round at top-rated golf courses around here, perfect for both beginners and seasoned players seeking scenic fairways.

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Preston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Savor the regional flavors by trying nearby eateries, which offer authentic cuisine that complements your stay in this charming area.
  • Plan outdoor activities: Take advantage of the natural scenery by engaging in outdoor pursuits such as walking, biking, or relaxing by the waterfront, making your visit memorable.
  • Connect with the community: Engage with locals or participate in community events to gain insights and enhance your experience in this welcoming region.
  • Choose a convenient rental location: Opt for a rental by owner near key attractions or amenities, ensuring easy access and a comfortable base during your time here.

Transportation Options

  • Preston Bus Service: This regional bus system offers convenient transportation throughout the area, making it easy for you to explore Preston and its surroundings.
  • Marina Taxi & Limousine: Providing reliable taxi and limousine services, this option ensures comfortable travel within the region for both short trips and special occasions.
  • Local Car Rentals: Several local agencies offer car rental services, giving you the flexibility to explore more of the region at your own pace.
  • Bike Rentals: For eco-friendly travelers, bike rentals are available in the area, allowing you to enjoy Preston’s scenic views and outdoor spaces actively.

Local Customs Options

  • Southern Hospitality: Expect warm welcomes and friendly interactions that reflect the region’s reputation for genuine Southern hospitality.
  • Local Seafood Traditions: Savor the area's culinary customs by indulging in fresh, locally caught seafood prepared using longstanding regional techniques.
  • Historic Preservation Practices: Appreciate the community’s commitment to maintaining historic sites and preserving the region’s cultural heritage.
  • Community Festivals: Participate in seasonal festivals that highlight local customs, crafts, and music deeply rooted in the area’s traditions.

Frequently Asked Questions About Preston Rentals by Owner

1. What are the top vacation rentals in Preston?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 57 in the Preston 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 Preston. 

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

The cancellation policy varies by listing. To understand the specific terms, please review the details provided on the property listing or contact the host directly for clarification.

4. How do I communicate with the property owner before booking in Preston, Maryland?

You can reach out to the property owner through the messaging platform provided on the booking page to ask questions or seek additional information before confirming your reservation.

5. Are there any house rules I should be aware of when booking a rental in the area?

Yes, each rental by owner typically has its own set of house rules. These are detailed in the listing description, so be sure to read them carefully before completing your booking.

6. What amenities are usually included in rentals by owner in Preston, Maryland?

Amenities vary depending on the property, but common features include Wi-Fi, parking, and kitchen facilities. For specifics, please consult the individual listing details or contact the host directly.

7. How can I ensure my stay in this destination is safe and secure?

Safety measures and security features are outlined in each listing. It's recommended to communicate with the owner if you have concerns or need further assurance about safety during your stay.

More Rentals You May Like Near Preston

More Top-Rated Rentals by Owner in Preston Area