Discover Your Perfect New Windsor Vacation Homes

New Windsor Luxury Rentals

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9.4 (22 Reviews)
Bed & Breakfast
Georges on York B&B
  • Air Conditioner
  • Parking
  • TV
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New Windsor Pet Friendly Vacation Rentals

7.2 (606 Reviews)
Hotel
The Boston Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your New Windsor 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 New Windsor

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit can enhance your experience here, as the region offers different charms throughout the year that suit a variety of interests and preferences.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area experiences warm weather ideal for outdoor activities and exploring local attractions, making it a popular choice for travelers seeking pleasant conditions and lively local events.

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

This season offers mild temperatures and beautiful fall foliage, attracting visitors looking to enjoy the region's scenic beauty and comfortable climate before the cold winter months set in.

Average Temperature Daytime: 70°F to 78°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

Cold weather and decreased tourist activity characterize this time, offering a quieter experience for those who prefer tranquility and lower rates for vacation rentals during their stay.

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

As the region transitions into winter, fewer visitors come, providing an ideal opportunity for travelers seeking solitude and better deals on accommodations while enjoying the peaceful ambiance of 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 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 New Windsor

More Top-Rated Vacation Rentals in New Windsor 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 a fully equipped patio or barbecue area, perfect for gatherings amid the scenic surroundings.
  • Relax in a private backyard with lush landscaping, offering a peaceful retreat in this charming region.
  • Take advantage of spacious lawns ideal for outdoor activities such as playing catch or setting up a picnic.
  • Benefit from a swimming pool or hot tub to unwind outdoors after exploring the area's attractions.
  • Use a fire pit or outdoor fireplace to gather around and share stories under the stars in this inviting destination.
  • Explore nearby hiking or walking trails accessible directly from the property, allowing you to immerse yourself in nature.
  • Make the most of a covered porch or balcony that invites you to enjoy fresh air and beautiful views throughout your stay.

Top Attractions Around New Windsor

What attractions are nearby?

In this area, you can explore a variety of outdoor activities and scenic spots to enjoy your stay in New Windsor, Maryland, ensuring a relaxing and engaging experience close to your vacation rentals.

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Family Activities

  • Walk through the C & O Canal National Historical Park: Enjoy a family-friendly hike or bike ride along this scenic trail that offers a glimpse into the region’s rich history and natural beauty.
  • Explore the local parks and outdoor spaces: Spend quality time at nearby parks that feature playgrounds, open fields, and picnic areas perfect for relaxing with your loved ones.
  • Visit educational centers and museums in the area: Engage with interactive exhibits and learn about the area's history and ecology in family-oriented museums close to your vacation rental.
  • Participate in community events and seasonal festivals: Experience local culture through festivals, fairs, and special family-friendly activities that foster fun and lasting memories during your stay here.
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Adult Activities

  • Historic Civil War Sites: Explore the region’s rich history by visiting notable Civil War landmarks that offer insightful tours and educational exhibits.
  • Scenic Nature Trails: Enjoy outdoor adventures on well-maintained trails perfect for hiking, biking, or simply soaking in the natural beauty of the area.
  • Indulge in tastings at nearby wineries and breweries, experiencing the region’s unique flavors and craftsmanship.
  • Golf Courses: Play a round at top-rated golf courses that showcase picturesque landscapes and provide a relaxing challenge for enthusiasts.

Other Places to Stay in New Windsor, MD

Elk Run Vineyards
Elk Run Vineyards Vacation Rentals
More Places to Stay Near New Windsor

New Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area’s calendar to align your stay with local happenings, enhancing your experience in this charming destination.
  • Explore Nearby Nature Spots: Take advantage of the region's outdoor spaces by scheduling outdoor activities that showcase its scenic beauty.
  • Book Your Stay During Peak Seasons: Secure your preferred vacation rentals well in advance to ensure availability during popular travel times in this destination.
  • Utilize Local Resources: Reach out to local hosts or property managers for insider tips and personalized recommendations to enrich your visit here.

Transportation Options

  • Interstate 70: This major highway provides quick and easy access to the region’s attractions and connects you to nearby cities, making road travel convenient for exploring the area.
  • Western Maryland Rail Trail: A popular choice for cycling and leisurely walks, offering scenic views and a peaceful way to experience the natural beauty of this destination.
  • Local Bus Services: Public bus options serve the community and surrounding areas, providing an economical transportation method for getting around here.
  • Nearby Baltimore/Washington International Thurgood Marshall Airport: Located within a reasonable drive, it offers domestic flights that make traveling from afar seamless when staying in this part of Maryland.

Local Customs Options

  • Community Events and Festivals: Participating in local festivals and community events allows you to experience the region's rich traditions and welcoming spirit.
  • Traditional Appalachian Cuisine: Enjoying regional dishes offers an authentic taste of the area's culinary heritage, reflecting its historical and cultural influences.
  • Respect for Nature and Outdoor Activities: Engaging in outdoor pursuits while respecting natural sites highlights the area's dedication to preserving its scenic beauty.
  • Greetings and Social Etiquette: Friendly greetings and courteous interactions are customary here, enhancing your immersive experience in the local culture.

Frequently Asked Questions About New Windsor?

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. Which vacation homes in New Windsor are best for families?

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

3. 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 64 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. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the host directly to understand the terms before booking.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the listing details. It's recommended to read these carefully or reach out to the property owner for clarification.

6. How do I ensure my reservation is secure and confirmed?

Reservations are secured through the booking platform once you complete the payment process. For confirmation details or special requests, contacting the host directly can provide additional assurance.

7. What amenities are usually included with vacation rentals in this region?

Amenities vary between properties, but common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Check each listing for a detailed list of what’s included.

8. Is there a minimum stay requirement for booking a vacation rental here?

Minimum stay requirements differ among properties. Be sure to review the booking terms on the listing or contact the owner to confirm any restrictions before making your reservation.