Discover Your Perfect Preston Vacation Homes

Why Choose Rent By Owner for your Preston Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as the best seasons for exploring this destination’s natural beauty and local events vary throughout the year.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area experiences warm weather, making it ideal for outdoor activities and enjoying the scenic landscape. The pleasant climate attracts visitors seeking a comfortable and relaxing stay.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to October)

This time of year offers cooler temperatures and vibrant foliage, providing a picturesque setting for your visit. It is a popular season for travelers looking to explore the charming surroundings comfortably.

Average Temperature Daytime: 70°F to 78°F - Nighttime: 50°F to 58°F

Off-Season Highlights

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Winter (December to February)

In the cold winter months, fewer visitors come to the area, offering a quieter experience. If you prefer serene settings and crisp, cool air, this is an excellent time to book your vacation rental here.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Early Spring (March to April)

Before the peak bloom, the region sees fewer tourists. This off-peak period allows for more flexible accommodation options and a peaceful environment to enjoy the changing season.

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

Weekly Weather Forecast for Preston

How to Book Your Preston Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals in Preston Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 with picnic tables or barbecue grills available at many properties in the area.
  • Relax on your private or shared outdoor patios and decks that offer scenic views of the surrounding landscape.
  • Take advantage of well-maintained gardens or landscaped yards for peaceful outdoor relaxation.
  • Make the most of fishing opportunities near water bodies or designated fishing areas close to the property.
  • Benefit from access to outdoor swimming pools that provide a refreshing way to unwind during your stay.
  • Utilize spacious lawns or open fields perfect for outdoor activities, games, or picnics.
  • Explore nearby nature trails or walking paths that allow you to enjoy the natural beauty of this destination firsthand.

Top Attractions Around Preston

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities and local attractions that showcase the natural beauty and charm of this destination, making it an ideal choice for your stay in Preston, Maryland.

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Family Activities

  • Point Lookout State Park: Enjoy a day exploring this scenic state park, perfect for family picnics, fishing, and observing local wildlife along the Chesapeake Bay.
  • Calvert Marine Museum: Discover fascinating marine exhibits, historic lighthouse tours, and interactive displays that bring the region's maritime history to life for all ages.
  • St. Mary's City Historic Site: Step back in time at this living history museum where your family can learn about early colonial life and explore authentic reenactments.
  • Chesapeake Beach Water Park: Make a splash at this seasonal water park offering thrilling slides and relaxing pools, ideal for a fun-filled day with kids.
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Adult Activities

  • Fishing at Hoopers Island: Enjoy a peaceful day by the water, casting your line in one of the region’s renowned fishing spots here.
  • Exploring Chesapeake Bay Maritime Museum: Discover the region's rich maritime history through engaging exhibits and boat tours in nearby St. Michaels.
  • Bird Watching in Blackwater National Wildlife Refuge: Observe diverse bird species and unwind amidst scenic natural surroundings in this wildlife haven close to here.
  • Boating and Water Activities: Take advantage of the area's waterways for kayaking, boating, or sailing adventures that suit all skill levels.

Other Places to Stay in Preston, MD

Tanyard
Tanyard Vacation Rentals
More Places to Stay Near Preston

Preston Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Sample the region’s fresh seafood and farm-to-table dishes to fully experience the culinary delights of this destination.
  • Visit Scenic Outdoor Spots: Take advantage of outdoor activities like boating, fishing, or walking along the water to enjoy the area's natural beauty.
  • Plan Off-Peak Visits: Consider visiting during less busy seasons to enjoy a more relaxed atmosphere and better access to popular attractions.
  • Engage with Community Events: Check local calendars for festivals or markets that can enrich your stay and offer a glimpse into local culture.

Transportation Options

  • Preston Bus Service: Regular local bus routes connect the area with nearby towns, offering an affordable and convenient transportation option for your stay.
  • Car Rentals: Several car rental agencies are available here, providing flexibility to explore Preston and its scenic surroundings at your own pace.
  • Taxi Services: Reliable taxi companies serve the region, ensuring quick and comfortable transportation for short trips or airport transfers.
  • Marina and Water Taxis: For a unique experience, water taxis operate in this destination, offering scenic rides across local waterways and access to waterfront activities.

Local Customs Options

  • Crab Feast Tradition: Participating in the local crab feasts is a cherished custom here, where you can enjoy fresh Maryland blue crabs seasoned with Old Bay, embodying the region's seafood heritage.
  • Waterfowl Hunting Etiquette: If you venture into the area's natural preserves, you'll find that waterfowl hunting follows specific customs emphasizing respect for wildlife and the environment.
  • Harbor Celebrations: Celebrating the region's maritime history through local festivals and events allows visitors to embrace the community spirit ingrained in this destination.
  • Preservation of Historic Sites: Respect for historic landmarks and adherence to local guidelines when visiting helps preserve the area's rich cultural legacy for future generations.

Frequently Asked Questions About Preston?

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 vacation rentals have private pools in Preston?

There are 12 vacation rentals with private pools near Preston. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Preston are best for families?

If you are looking for a family-friendly vacation home in Preston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Preston:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 84 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. 

5. What is the cancellation policy for vacation rentals in Preston, Maryland?

The cancellation policy varies by listing, so it’s important to review the specific terms outlined on the property page. You can also contact the host directly for detailed information regarding any potential fees or restrictions.

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

Additional fees such as cleaning, service charges, or local taxes may apply depending on the property. Details are usually provided during the booking process, but it’s recommended to read the entire listing or reach out to the owner for clarification.

7. How do I find the best vacation rental deals in Preston, Maryland?

To secure the best rates, use the search filters and compare different properties based on your preferences. Booking during off-peak times or staying longer can often provide discounts. Always review the total price before confirming your reservation.

8. What amenities should I look for to ensure a comfortable stay in Preston, Maryland?

Consider essential amenities like Wi-Fi, fully equipped kitchens, parking, and laundry facilities. Reading the property description carefully will help you identify which rentals offer the comforts you need for an enjoyable stay.

9. How can I contact the property owner if I have questions about my reservation or the rental property?

Most listings feature a messaging system that allows you to communicate directly with the owner or host. This is the best way to ask specific questions about the property, clarify details, or request additional information before finalizing your booking.