Best Vacation Homes in Highland Falls
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
969 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
£287/Night
7 Nights - £2,006
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
1829.86 ft²
- Parking
Internet
Child Friendly
Security/Safety
£540/Night
7 Nights - £3,780
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£458/Night
7 Nights - £3,206
Apartment
10.0(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
£190/Night
7 Nights - £1,328
House
9.5(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1743.75 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
£253/Night
7 Nights - £1,774
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Parking
Air Conditioner- Internet
£144/Night
7 Nights - £1,008
Apartment
9.8(35 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£285/Night
7 Nights - £1,994
Apartment
9.8(23 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
£296/Night
7 Nights - £2,070
Highland Falls Luxury Rentals
House
10.0(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
£875/Night
7 Nights - £6,126
House
10.0(1 Review)
6 Bedrooms
4 Baths
15 Guests
1991 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£723/Night
7 Nights - £5,057
House
10.0(1 Review)
5 Bedrooms
3 Baths
10 Guests
3500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£696/Night
7 Nights - £4,871
House
9.8(8 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
£450/Night
7 Nights - £3,149
House
10.0(7 Reviews)
4 Bedrooms
2 Baths
8 Guests
1824 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
£424/Night
7 Nights - £2,966
House
9.8(12 Reviews)
4 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£418/Night
7 Nights - £2,923
House
10.0(19 Reviews)
3 Bedrooms
2 Baths
6 Guests
1680 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
£414/Night
7 Nights - £2,898
House
9.8(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£405/Night
7 Nights - £2,833
Highland Falls Pet Friendly Vacation Rentals
Apartment
9.6(27 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
£256/Night
7 Nights - £1,791
Apartment
8.5(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
1001.04 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
£229/Night
7 Nights - £1,602
House
10.0(3 Reviews)
1 Bedroom
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£225/Night
7 Nights - £1,576
Apartment
1 Bedroom
1 Bath
6 Guests
1097.92 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
£224/Night
7 Nights - £1,568
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£288/Night
7 Nights - £2,014
House
1 Bedroom
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£239/Night
7 Nights - £1,674
House
1 Bedroom
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£238/Night
7 Nights - £1,669
House
10.0(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
1320 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
£356/Night
7 Nights - £2,492
Highland Falls Large Vacation Homes
House
10.0(11 Reviews)
5 Bedrooms
3 Baths
12 Guests
3100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£422/Night
7 Nights - £2,953
Cottage
10.0(1 Review)
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£707/Night
7 Nights - £4,946
Why Choose Rent By Owner for your Highland Falls 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 Highland Falls
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here ensures you enjoy the region's natural beauty and peaceful atmosphere, making your stay in Highland Falls, New York, a truly memorable experience.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences warm weather, making it ideal for enjoying outdoor activities and scenic views. The region’s lively atmosphere attracts visitors seeking a vibrant getaway.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to November)
Early fall offers crisp air and stunning foliage, drawing travelers who want to witness the area's natural beauty in full color. It’s a popular time for those seeking a peaceful retreat amidst autumnal landscapes.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
In winter, the area transforms into a serene winter wonderland, appealing to visitors interested in quieter stays and seasonal tranquility. Cold temperatures make it perfect for cozying up in your vacation rental.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Spring (March to May)
Springtime brings milder weather and blooming scenery, attracting those looking to enjoy a more relaxed visit without the peak crowds. It’s an excellent period for exploring the region’s natural charm.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Highland Falls
How to Book Your Highland Falls 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 Highland Falls
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 spacious outdoor patio perfect for relaxing and dining al fresco in this scenic destination.
- Make the most of the lush garden areas, ideal for leisurely strolls or outdoor gatherings.
- Take advantage of a private backyard space equipped with a barbecue grill for family cookouts.
- Use the nearby fire pit to gather with loved ones under the stars after a day of exploring.
- Benefit from access to scenic hiking trails and nature walks right from your rental property.
- Relax on outdoor loungers while soaking up the tranquil atmosphere of this area’s natural beauty.
- Utilize the available outdoor recreational equipment, such as bikes or kayaks, to explore the region’s outdoor offerings.
Top Attractions Around Highland Falls
What attractions are nearby?
In this scenic region, you can enjoy a variety of outdoor activities such as exploring local parks, hiking along picturesque trails, or discovering historic sites that capture the area's rich heritage and natural beauty.
Family Activities
- West Point Museum: Dive into military history with your family at this engaging museum located nearby, offering educational exhibits about the United States Military Academy.
- Bear Mountain State Park: Enjoy outdoor adventures such as hiking, picnicking, and scenic views within this expansive park just a short drive from here, perfect for family outings.
- Hudson Highlands Cruises: Experience the region from a new perspective through relaxing boat tours that provide stunning views of the Hudson River and surrounding landscapes.
- Anthony's Nose Trail: Take a family hike up this trail for breathtaking vistas of the river and mountains, ideal for those seeking outdoor exploration in the area.
Adult Activities
- Exploring West Point Military Academy: You can tour this historic military academy renowned for its impressive architecture and rich history, offering a unique glimpse into the region's significant past.
- Hiking in Bear Mountain State Park: Enjoy scenic trails and panoramic views at this nearby state park, providing an ideal outdoor adventure just minutes from your vacation rental.
- Visit the Hudson River Waterfront: Relax along the picturesque riverfront where you can take leisurely walks, enjoy local cafes, or simply soak in the serene water views.
- Discover Local Golf Courses: Tee off at well-maintained golf courses in the area that cater to enthusiasts looking for a leisurely day on the greens amidst peaceful surroundings.
Other Places to Stay in Highland Falls, NY
West Point Museum
Highland Falls Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining and shopping: Take advantage of the area's charming eateries and boutiques to get a true taste of the region's hospitality and culture.
- Plan outdoor activities: Make the most of the scenic surroundings by scheduling hikes, walks, or outdoor adventures that showcase the natural beauty here.
- Visit nearby attractions: Discover the renowned sites and landmarks in this destination to enrich your stay with memorable experiences.
- Utilize nearby amenities: Select a vacation rental that offers convenient access to essential services and facilities for a comfortable visit here.
Transportation Options
- New York State Thruway (I-87): You can easily access this major highway to travel conveniently to and from the region, making it ideal for road trips around Highland Falls and nearby areas.
- West Point Bus Service: This local bus service provides reliable transportation options within the area, connecting you effortlessly to key destinations around Highland Falls and beyond.
- AmeriCabs Taxi Service: For quick and convenient travel within the region, taxi services offer flexible options to explore Highland Falls and surrounding locations comfortably.
- Metropolitan Transportation Authority (MTA): With accessible train routes in nearby towns, the MTA helps you easily reach New York City or other parts of the state, enhancing your travel experience here.
Local Customs Options
- Respect for Military Traditions: You’ll find that honoring the military history is a significant custom here, reflecting the area's proximity to West Point and its proud military heritage.
- Community Celebrations: Participating in local festivals and parades allows you to connect with residents who cherish their community spirit and shared traditions.
- Preservation of Local Heritage: Visitors are encouraged to appreciate and respect historic landmarks and sites that showcase the region's rich past.
- Outdoor Etiquette: When enjoying the scenic outdoor spaces, it’s customary to follow guidelines that maintain the natural beauty and serenity of the area.
Frequently Asked Questions About Highland Falls?
1. What are the top vacation rentals in Highland Falls?
There are a lot of options in Highland Falls. If you plan on staying in the Highland Falls area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Highland Falls:
- Updated Home w/Patio Half Mile to West Point
- Modern West Point House near USMA - 3 bed, 2 bath with Hot tub & Fire pit!
- Charming Highland Falls Home < 2 Mi to West Point!
- Historic home at West Point on Main Street. 1 mile from Thayer Gate!
- House on the Babbling Brook- Quiet 2BR + King Bed!
- Home: 2 Mi to Thayer Gate at U.S. Military Academy
- Lovely 3BR Home with parking-Walk to WP Gate!
- Beautiful First Flr, 2-Bedroom Apt w/Free Parking
- Luxury home near West Point
- Cozy 3bedroom home in Highland Falls, only a five-minute walk from West Point NY
2. Which vacation homes in Highland Falls are best for families?
If you are looking for a family-friendly vacation home in Highland Falls, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Highland Falls:
3. How many Rentbyowner vacation rentals are available in Highland Falls?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 59 in the Highland Falls 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 Highland Falls.
4. What is the cancellation policy for vacation rentals in Highland Falls, New York?
The cancellation policies vary depending on the specific property you choose. You should review the listing details or contact the owner directly to understand the terms and any associated fees.
5. How do I find the best vacation rental deals in Highland Falls?
To secure the best deals, compare different listings in the area, pay attention to guest reviews, and consider booking during off-peak seasons. Details about discounts or special offers are typically available on each property's page.
6. Are there any specific amenities included with vacation rentals here?
Amenities vary by property, so it’s important to check each listing for features like Wi-Fi, parking, kitchen facilities, or outdoor spaces. Contact the host if you have particular needs or questions.
7. What should I know about the check-in and check-out process for rentals in this region?
Check-in and check-out times are listed on each property’s page. For a smooth experience, confirm these details with the owner beforehand and inquire about flexible arrangements if needed.
8. Is there a specific cleaning protocol for vacation rentals in Highland Falls?
Cleaning procedures are set by individual hosts and may include enhanced disinfecting measures. Review the listing details or reach out to the owner for information on sanitation practices and safety protocols.
Highland Falls Top Rated Vacation Rentals
House
5.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
Private Pool
Pool- Balcony/Terrace
- Kitchen
£232/Night
7 Nights - £1,624
House
4.9(31 Reviews)
1 Bedroom
1 Bath
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
£129/Night
7 Nights - £902
