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  3. Frederick
  4. New Windsor
  5. Rentals by Owner

Discover Your Perfect New Windsor Rentals by Owner

New Windsor Rentals by Owner

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Westminster
  • Air Conditioner
  • Parking
  • Transportation/Shuttle
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More Top-Rated Rentals by Owner in New Windsor Area

Why Choose Rent By Owner for your New Windsor 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 New Windsor

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider visiting during the right season when the weather is favorable and local events align with your interests, ensuring a memorable vacation experience in this charming destination.

Peak Season Highlights

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Late Spring to Early Summer (May to June)

This period offers warm weather ideal for enjoying the outdoor scenery and making the most of your stay in the area. It’s a popular time for booking rental by owner accommodations that provide comfort and privacy.

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

The early fall months bring pleasant temperatures and vibrant foliage, making it an excellent season for exploring this destination. Many visitors choose to reserve their rental by owner during these months for a serene getaway experience.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

During the winter, the region experiences cooler temperatures, which might appeal to travelers seeking a quiet retreat. Rental homes can be more available and offer cozy amenities perfect for the cold season.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 25°F to 35°F
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Late Fall (November to early December)

As the temperatures drop and the holiday season approaches, this is a quieter time to visit. Booking a rental by owner now means you can enjoy the peaceful ambiance and prepare for a festive season in the area.

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

Weekly Weather Forecast for New Windsor

How to Book Your New Windsor 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 New Windsor

More Top-Rated Rentals by Owner in New Windsor 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 lounging with a private patio or deck to relax in the fresh air.
  • Take advantage of a spacious backyard or garden area suitable for outdoor activities and gatherings.
  • Make use of a barbecue grill for outdoor cooking and dining experiences during your stay.
  • Benefit from access to scenic walking trails or nearby parks perfect for exploration and exercise.
  • Utilize a fire pit for cozy evenings and enjoying the region’s cool evenings outdoors.
  • Experience outdoor playing areas, such as a swing set or sports field, ideal for family fun.
  • Observe local wildlife or star gaze from a well-maintained outdoor space designed for nature appreciation.

Top Attractions Around New Windsor

What attractions are nearby?

During your stay here, you can enjoy a variety of outdoor activities, local parks, and scenic trails that showcase the natural beauty of the region, making it an ideal location for exploring and relaxing in New Windsor, Maryland.

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Family Activities

  • Windsor Knolls Recreation Park: Enjoy outdoor activities like playgrounds, walking trails, and sports fields perfect for a family day out.
  • The Musket Ridge Golf Course: Discover family-friendly golf options and scenic views that make for an enjoyable outing in the area.
  • Historic New Windsor Heritage Center: Explore local history through engaging exhibits and programs tailored for curious young minds and adults alike.
  • Northern Maryland Discovery Trail: Take a family hike or bike ride along this scenic trail that showcases the natural beauty of this region.
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Adult Activities

  • Hiking and Nature Walks: Explore scenic trails in the area to enjoy the region's natural beauty and tranquility.
  • Visit Local Museums: Discover the area's history and culture by exploring nearby museums that offer engaging exhibits.
  • Golfing Experiences: Play a round at local golf courses that cater to all skill levels, providing relaxation and recreation.
  • Dining at Local Eateries: Savor regional cuisine by dining at popular restaurants that showcase the area's culinary delights.

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New Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and shopping options: Take advantage of the area’s charming eateries and shops to enjoy authentic regional flavors and handmade goods during your stay.
  • Plan outdoor activities wisely: Make the most of the region’s natural beauty by scheduling outdoor adventures like hiking or picnicking at nearby parks or scenic spots.
  • Connect with the community: Engage with local events or markets to gain a deeper appreciation of the destination’s culture and hospitality.
  • Utilize personalized rental options: Book directly through Rent By Owner to access private accommodations that offer comfort, privacy, and tailored amenities here in the region.

Transportation Options

  • Car Rental Services: Booking a rental car offers you the flexibility to explore the region at your own pace, with numerous providers conveniently available nearby.
  • Public Transit: Local bus services provide an economical and eco-friendly way to navigate this destination and its surrounding areas.
  • Taxi and Ride-Sharing: Taxis and ride-sharing options like Uber and Lyft deliver convenient transportation for quick trips within the area.
  • Bike Rentals: Renting a bike can be a pleasant and sustainable way to discover the scenic routes and local attractions here.

Local Customs Options

  • Respect for Local History: You’ll find that honoring the area's historical sites and stories is highly valued by residents, enriching your experience in this charming destination.
  • Community Festivals: Participating in or observing local festivals here offers a glimpse into the region’s vibrant cultural traditions and community spirit.
  • Southern Hospitality: Expect warm welcomes and friendly interactions, reflecting the region’s reputation for genuine hospitality and inviting atmospheres.
  • Environmental Conservation: The area places importance on preserving its natural surroundings, encouraging visitors to practice eco-friendly behaviors during their stay.

Frequently Asked Questions About New Windsor Rentals by Owner

1. What are the top vacation rentals in New Windsor?

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

2. How many Rentbyowner vacation rentals are available in New Windsor?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 39 in the New Windsor 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 New Windsor. 

3. What is the cancellation policy for rental properties in this area?

Cancellation policies vary by listing, so it’s important to review the specific terms provided by the owner on each rental page. You can find detailed information regarding cancellations and potential fees there or contact the host directly for clarification.

4. How do I know if my booking with a rental owner is secure?

All bookings made through Rent By Owner are protected by secure payment systems and verified listings. For added peace of mind, check if the property has verified reviews and contact the owner if you have any concerns before confirming your reservation.

5. Are there any special amenities available in vacation rentals here?

Amenities differ between properties; details about features like Wi-Fi, parking, or pet-friendliness are included in each listing. If you need certain amenities, reach out directly to the owner to confirm availability before completing your booking.

6. What should I do if I need to modify my reservation?

Modifications to your stay, such as dates or guest numbers, depend on the owner’s policies. Review the specific listing’s terms or contact the owner directly through the platform to request changes to your booking.

7. Is there a minimum stay requirement for rentals in this destination?

Minimum stay requirements vary depending on the property. You can find this information in the individual listing details, or contact the owner directly if you have particular dates in mind to ensure they accommodate your plans.

More Rentals You May Like Near New Windsor

More Top-Rated Rentals by Owner in New Windsor Area