Best Vacation Homes in New Windsor
Cottage
10.0(35 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $504/Night
7 Nights - US $3,525
Bed & Breakfast
10.0(1 Review)
14 Bedrooms
14 Baths
28 Guests
400.57 ft²
- Balcony/Terrace
View- Parking
Air Conditioner
US $726/Night
7 Nights - US $5,082
House
10.0(1 Review)
1 Bedroom
1 Bath
- Balcony/Terrace
Pet Friendly- Parking
Internet
US $502/Night
7 Nights - US $3,514
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $272/Night
7 Nights - US $1,902
House
9.2(5 Reviews)
3 Bedrooms
2 Baths
7 Guests
1399.31 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $845/Night
7 Nights - US $5,915
House
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $223/Night
7 Nights - US $1,564
House
9.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $343/Night
7 Nights - US $2,398
Apartment
2.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
Hot Tub- Fireplace/Heating
- Kitchen
- Parking
US $115/Night
7 Nights - US $807
New Windsor Luxury Rentals
House
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Air Conditioner
- Internet
US $7,402/Night
7 Nights - US $51,815
Cabin
9.6(5 Reviews)
4 Bedrooms
4 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,577/Night
7 Nights - US $11,038
House
10.0(10 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
US $1,345/Night
7 Nights - US $9,413
New
Cabin
4 Bedrooms
1 Bath
8 Guests
32291.73 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
US $1,150/Night
7 Nights - US $8,050
House
8.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2688 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $856/Night
7 Nights - US $5,992
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $661/Night
7 Nights - US $4,627
House
10.0(65 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $578/Night
7 Nights - US $4,047
House
4 Bedrooms
2 Baths
8 Guests
1730 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $563/Night
7 Nights - US $3,943
New Windsor Pet Friendly Vacation Rentals
House
10.0(30 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $471/Night
7 Nights - US $3,295
Hotel
9.1(169 Reviews)
1 Bath
387.5 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Parking
US $257/Night
7 Nights - US $1,798
House
10.0(10 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $355/Night
7 Nights - US $2,486
Hotel
7.7(446 Reviews)
7 Baths
356.74 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Pet Friendly
US $115/Night
7 Nights - US $808
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $479/Night
7 Nights - US $3,352
Apartment
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $305/Night
7 Nights - US $2,138
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $553/Night
7 Nights - US $3,868
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $898/Night
7 Nights - US $6,284
New Windsor Large Vacation Homes
House
7 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $1,911/Night
7 Nights - US $13,378
House
7 Bedrooms
5 Baths
18 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $1,590/Night
7 Nights - US $11,133
Villa
10.0(4 Reviews)
3 Bedrooms
5 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,364/Night
7 Nights - US $9,545
House
7.8(8 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
Breakfast- Pet Friendly
- Kitchen
US $302/Night
7 Nights - US $2,114
Villa
5.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1104 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
US $145/Night
7 Nights - US $1,015
House
4.9(7 Reviews)
4 Bedrooms
2 Baths
12 Guests
2400 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $506/Night
7 Nights - US $3,542
Villa
4.0(3 Reviews)
7 Bedrooms
4 Baths
17 Guests
1 ft²
- Private Pool
- Pool
- Air Conditioner
Child Friendly
US $740/Night
7 Nights - US $5,180
Why Choose Rent By Owner for your New Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 right time to visit can enhance your experience, so consider planning your stay here during the local seasons when outdoor activities and natural beauty are at their peak for a memorable getaway.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather perfect for outdoor activities and exploring this destination’s natural beauty. This is the busiest time of year, so expect vibrant local events and a lively atmosphere.
Average Temperature Daytime: around 80-85°F - Nighttime: around 60-65°F
Fall (September to November)
Autumn offers stunning foliage views, making it an ideal time for sightseeing and outdoor adventures in the region. The pleasant weather attracts many visitors seeking a scenic escape before winter sets in.
Average Temperature Daytime: about 70-75°F - Nighttime: around 50-55°F
Off-Season Highlights
Winter (December to February)
During the colder winter months, fewer travelers visit, providing a quieter experience for those seeking tranquility. You can find cozy stays and enjoy off-season rates in the area.
Average Temperature Daytime: around 30-40°F - Nighttime: about 20-25°F
Spring (March to May)
Early spring brings mild temperatures and blossoming scenery, making it a peaceful time to explore while avoiding the peak crowds. It’s an excellent season to discover this area's natural charms at a leisurely pace.
Average Temperature Daytime: around 50-65°F - Nighttime: about 35-45°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
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 a private outdoor patio or deck for relaxing and dining al fresco amid the scenic surroundings.
- Take advantage of a spacious backyard ideal for outdoor games, picnics, and family gatherings.
- Look for outdoor grilling stations or BBQ areas to prepare meals while enjoying the fresh air.
- Benefit from access to well-maintained gardens or landscaped lawns that enhance your outdoor experience.
- Discover patio furniture including loungers and umbrellas to maximize comfort during sunny days.
- Utilize outdoor fire pits or fireplaces perfect for evening relaxation and storytelling under the stars.
- Check for nearby walking trails, gardens, or parks accessible directly from your rental for outdoor exploration in this inviting region.
Top Attractions Around New Windsor
What attractions are nearby?
While staying in the area, you'll find a variety of outdoor activities and cultural experiences nearby, allowing you to explore the best that this destination has to offer.
Family Activities
- Dogs for Kids Play Area: Spend quality time at this family-friendly park where children can enjoy a safe and engaging space to play, making it perfect for outdoor activities in the area.
- Hudson Valley Rail Trail: Explore scenic biking and walking trails suitable for all ages, offering a wonderful way to experience the natural beauty of the region with your loved ones.
- Garrison Art Center: Engage in artistic adventures by visiting this vibrant center that offers family-friendly workshops and exhibitions, fostering creativity here in the region.
- The Castle Fun Center: Have an exciting day filled with indoor amusement rides and games designed specifically for kids and families seeking fun in this destination.
Adult Activities
- Visit the National Purple Heart Hall of Honor: Engage with American military history at this meaningful site, conveniently located within the area, offering a reflective experience during your stay.
- Explore Storm King Art Center: Discover an expansive outdoor sculpture park showcasing contemporary art amid scenic landscapes, perfect for a leisurely day out here.
- Enjoy outdoor activities at the Hudson Valley Rail Trail: Cycle, walk, or run along this scenic trail that provides stunning views of the region's natural beauty and is ideal for active adults.
- Experience local craft breweries in the area: Sample unique regional brews and enjoy a relaxed atmosphere at popular breweries, enhancing your visit to this destination.
Other Places to Stay in New Windsor, NY
Vails Gate
Horizon Family Medical Group
New Windsor Cantonment State Historic Site
National Purple Heart Hall of Honor
Knox's Headquarters State Historic Site
Kristi Babcock Memorial Park
New Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region's parks and trails to enjoy hiking, biking, or leisurely walks that showcase the area's natural beauty.
- Discover nearby dining options: Sample authentic regional cuisine at local eateries to enhance your stay and get a true taste of the area.
- Plan visits during off-peak hours: Visit popular attractions early in the day or later in the evening to avoid crowds and enjoy a more relaxed experience.
- Choose a well-located vacation rental: Select accommodations close to key sites and amenities to maximize your time exploring and minimize travel hassle in this destination.
Transportation Options
- New Windsor Transit Authority: Provides local bus services that connect you to key spots around the area for convenient travel during your stay.
- Stewart International Airport: Offers domestic and limited international flights, making it a practical gateway for travelers arriving from afar.
- Taxi and Rideshare Services: Reliable options like taxis and rideshare apps are readily available for flexible transportation throughout here and nearby attractions.
- Car Rentals: Numerous rental agencies in the region allow you to explore the area at your own pace with ease, especially when staying at one of the comfortable vacation rentals nearby.
Local Customs Options
- Local Craftsmanship: The area celebrates a rich tradition of craftsmanship, which you can experience through local markets showcasing handmade goods and artisan works.
- Community Festivals: Participating in neighborhood festivals offers a glimpse into the region's vibrant culture and close-knit community spirit.
- Traditional Dining Etiquette: Visitors often observe respectful dining customs, such as greeting with a handshake and engaging in friendly conversation, reflecting the area's welcoming atmosphere.
- Religious Observances: Respect for various religious practices is common, and attending local services or events can deepen your understanding of the area's diverse traditions.
New Windsor Vacation Rental Frequently Asked Questions
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:
- Cozy Cottage minutes to West Point
- Historic 1800s Cornwall-On-Hudson Cottage!
- Bright Cornwall-On-Hudson Vacation Rental!
- Hudson Valley Oasis - Hot Tub, Fireplace, 50mi NYC
- Cozy Easy Access to the Best of the Hudson Valley!
- Charming and private 3-bedroom home – minutes from West Point and Bear Mountain!
- Caldwell House Bed and Breakfast
- Cozy Easy Access to the Best of the Hudson Valley
- Charming Renovated Home, Cozy for All! Pet friendly!
- Light-Filled Apartment in Mountainville Barn
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 2026 is over 51 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 New Windsor, New York?
Cancellation policies vary depending on the property owner. You should carefully review the specific listing details and contact the property owner directly to understand the terms applicable to your booking.
5. How do I secure my reservation at a vacation rental in this area?
Reservations are typically confirmed through a secure booking process on the listing page. It’s recommended to read the booking instructions carefully and communicate with the property owner if you have any questions before confirming.
6. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or local taxes may apply. These fees are usually specified in the listing details, so reviewing the listing thoroughly will give you complete information.
7. What amenities can I expect in vacation rentals in this destination?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. To find accommodations that meet your needs, check the amenities listed on each property's page.
8. Is it possible to modify or cancel my booking after confirmation?
Modifications or cancellations depend on the property's individual policy. Contact the property owner directly through the platform to discuss your options and ensure your plans are flexible.
New Windsor Top Rated Vacation Rentals
Hotel
9.2(1004 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $179/Night
7 Nights - US $1,253
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1100 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $364/Night
7 Nights - US $2,548
Cottage
4.6(9 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $600/Night
7 Nights - US $4,200
House
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
Lake View
US $850/Night
7 Nights - US $5,950
House
1 Bedroom
2 Baths
3 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $129/Night
7 Nights - US $903
