Highland Falls holiday lettings

We found 388 holiday rentals — enter your dates for availability
Discover a selection of 22 homes, 10 apartments and other holiday rentals in Highland Falls that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and Wi-Fi. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Highland Falls

Showing deals for:6 Nov - 13 Nov

This sitting area is another great space to gather around the faux fireplace.
George Washington was president when these original hardwood floors were made!
Our home sits on 5 partially-wooded acres. Welcome to the country!
Here's the spacious farmhouse kitchen. A leaf expands the table to seat 6.
Exceptional
(19 reviews)

Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres

Milton

16% off
£1,920
for 7 nights, 1 home
£274 per night
includes taxes & fees
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Front of house. Lake in back.
Breathtaking View, Situated on Orange Lake
Open floor kitchen, LR, and DR, with panoramic view of lake.
Winter beauty
Exceptional
(325 reviews)

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh

8% off
£3,097
for 7 nights, 1 home
£442 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Living area
Private kitchen
Dining
Dining
Exceptional
(8 reviews)

Modern home w/creek view, steps to town & mountain

Beacon

7% off
£4,962
for 7 nights, 1 home
£709 per night
includes taxes & fees
Modern home w/creek view, steps to town & mountain
Original mahogany wood work and French Chandliers though out the house
View of the dining room
Hallway with pocket doors on main floor
Walk way to back yard from side of the house
Exceptional
(16 reviews)

Stunning historic Victorian house in Newburgh

Newburgh

20% off
£3,747
for 7 nights, 1 home
£535 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh
Outdoor dining
Living area
Pool
Private kitchen
Exceptional
(16 reviews)

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Harriman

11% off
£4,659
for 7 nights, 1 home
£666 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Terrace/patio
Exterior
Property grounds
Interior
Exceptional
(46 reviews)

Cosy lakefront cottage in Hudson Valley

Walden

7% off
£1,324
for 7 nights, 1 cottage
£189 per night
includes taxes & fees
Cosy lakefront cottage in Hudson Valley
Property grounds
Exterior
Interior
Living area
Wonderful
(12 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
£1,073
for 7 nights, 1 home
£153 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Dining
Outdoor spa tub
Room
Exterior
Exceptional
(11 reviews)

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

Cornwall

11% off
£2,494
for 7 nights, 1 home
£356 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Living area
Property grounds
Outdoor dining
Exterior
Exceptional
(8 reviews)

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.

Marlboro

11% off
£923
for 7 nights, 1 home
£132 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Dining
Main house. Apt is downstairs to the left.
Private entrance to apt.
Private kitchen
Exceptional
(21 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

20% off
£868
for 7 nights, 1 apartment
£124 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
Room
Living area
Dining
Outdoor dining
Exceptional
(27 reviews)

Hudson River Retreat

Newburgh

7% off
£1,157
for 7 nights, 1 apartment
£165 per night
includes taxes & fees
Hudson River Retreat

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Highland Falls getaway

Enjoy the churches and other features of Highland Falls. Renowned for its university setting, shopping and waterfalls, this city welcomes all visitors. Woodbury Common Premium Outlets and LEGOLAND® New York are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Highland Falls

Are you hoping to discover attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Highland Falls a fun place to get away to. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® New York (18 mi / 28.9 km)
  • Putnam County Golf Course (10.8 mi / 17.4 km)
  • Brotherhood Winery (11.1 mi / 17.8 km)
  • SplashDown Beach (12.7 mi / 20.5 km)
  • Ice Time Sports Complex (12.9 mi / 20.7 km)
  • Benmarl Vineyards and Winery (15.5 mi / 24.9 km)

Exploring the natural landscape of Highland Falls

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Highland Falls. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Boscobel House and Gardens (3.4 mi / 5.5 km)
  • Storm King State Park (4 mi / 6.4 km)
  • Hudson Highlands State Park (5 mi / 8.1 km)
  • Oscawana Lake (6.3 mi / 10.1 km)
  • Lake Tiorati Beach (9.1 mi / 14.6 km)
  • Lake Welch Beach (10.8 mi / 17.4 km)

Transport options to and around Highland Falls

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 11 mi (17.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to White Plains, NY (HPN-Westchester County), which is 24.8 mi (40 km) away.

Frequently asked questions

What is the best area to stay in Highland Falls when booking a holiday rental?
When considering a holiday rental in Highland Falls, New York, the area surrounding the village itself is certainly an appealing choice. Nestled at the foot of the scenic West Point Military Academy, this neighbourhood offers a unique blend of history and natural beauty. Visitors can enjoy delightful walks along the banks of the Hudson River, with breathtaking views of the surrounding mountains.One of the top attractions in the vicinity is the West Point Museum, which showcases an impressive collection of military artefacts and exhibits, making it an enriching experience for history enthusiasts. Additionally, the nearby Bear Mountain State Park provides ample opportunities for outdoor activities, including hiking, picnicking, and enjoying the stunning landscape.While the number of properties may vary, you can generally find a selection of charming holiday rentals that cater to different preferences, allowing you to fully immerse yourself in the area's serene atmosphere.
How much does it cost to rent a holiday home in Highland Falls?
Prices for holiday rentals in Highland Falls vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Highland Falls to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Highland Falls holiday house rentals?
You can find great discounts on house rentals in Highland Falls on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Highland Falls ski resort rentals?
For those interested in ski resort rentals near Highland Falls, the closest significant ski area is located in the nearby Bear Mountain State Park, just a short drive away. In the vicinity of Bear Mountain, travellers can find a variety of rental properties, particularly in the town of Highland Falls and along the nearby Hudson River. These accommodations often include charming cabins and lodges that come with amenities such as wood-burning fireplaces, spacious living areas, and fully equipped kitchens, ideal for families or groups.In Highland Falls itself, you may discover unique properties with a rustic charm, featuring outdoor spaces to enjoy the surrounding natural beauty. Many rentals offer convenient access to local restaurants and shops, providing a taste of the area's community spirit. Additionally, the proximity to hiking trails and scenic spots along the Hudson adds to the appeal for outdoor enthusiasts.For those venturing a bit further, the nearby town of Cornwall-on-Hudson also offers a range of rental options. Here, properties tend to feature modern amenities alongside traditional aesthetics, with some boasting beautiful views of the river and mountains.
What is the most popular type of holiday rental accomodation in Highland Falls?
In Highland Falls, holiday houses are the most popular type of holiday rental, with around 100 available throughout the area. These homes provide ample space, featuring multiple bedrooms, well-equipped kitchens, and often outdoor areas for relaxation and enjoying the scenic views of the nearby Hudson River. Many of these properties are situated in tranquil neighbourhoods, making them ideal for families or groups seeking a peaceful getaway. Additionally, there are about 28 apartments available, which typically include comfortable living spaces and modern amenities for a more compact stay. Cottages, while less common with only 12 in the area, offer a charming alternative for those looking for a quaint experience amidst nature.
Are there any family house rentals in Highland Falls?
In Highland Falls, there are a variety of family-friendly house rentals available, with around 17 options to choose from. This charming area is located near the scenic Hudson River and offers easy access to the picturesque landscapes of the Hudson Highlands. Many of the homes feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces that are great for children to play.Visitors will appreciate amenities such as Wi-Fi, air conditioning, and sometimes even backyards with barbecue facilities, enhancing the comfort of their stay. The proximity to attractions like the historic West Point Military Academy and the beautiful Bear Mountain State Park makes it an ideal location for families looking to explore nature and enjoy outdoor activities.
Can I find long-stay holiday rentals in Highland Falls?
A long-stay holiday rental in Highland Falls is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Highland Falls?
In Highland Falls, there are several pet-friendly house rentals available, with around eleven options to choose from. Many of these properties come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families and those travelling with pets.The town is close to the scenic Hudson Highlands State Park, which offers numerous trails and outdoor spaces great for walking dogs and enjoying nature. Additionally, the nearby West Point area provides historical sites and beautiful landscapes that can be explored with pets.
Are there any remote work holiday rentals in Highland Falls?
In Highland Falls, there are many options for remote work holiday rentals, with around 128 available in the area. This charming town, located near the Hudson River, provides a tranquil setting for those looking to balance work and leisure. Many of the properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desks, ensuring a productive environment during your stay.Visitors can enjoy beautiful views of the surrounding mountains and easy access to local attractions, including the historic West Point Military Academy and the scenic trails of the Hudson Highlands State Park. With a variety of accommodation styles ranging from cozy apartments to spacious homes, Highland Falls caters well to remote workers seeking both comfort and connectivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Highland Falls holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Highland Falls with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Highland Falls?
In Highland Falls, popular rental amenities include kitchens, allowing guests to prepare their own meals, and onsite parking for added convenience. Many properties also feature a coffee and tea maker for those who enjoy a warm beverage, a desk suitable for work or study, and a patio for outdoor relaxation.
When is the best time to visit Highland Falls for a holiday rental?
The best time to visit Highland Falls for a holiday rental is during the vibrant summer months, particularly in July, when the town buzzes with activity. This period, spanning from June to August, is ideal for those seeking outdoor adventures and breathtaking natural beauty. Warm temperatures, averaging around 20 to 30 degrees Celsius, create a great environment for exploring the stunning landscapes of the Hudson Highlands.During July, visitors can enjoy a variety of activities, from hiking the scenic trails of the nearby Bear Mountain State Park to experiencing the rich history at the United States Military Academy at West Point. The lively option and numerous outdoor events make it an exciting time to engage with fellow travellers and immerse yourself in the local culture.For those looking to save a bit on their accommodation, consider planning your visit in December. During this time, the winter landscape has its own charm, making it an excellent time for peaceful retreats and cosy gatherings.
How early should I book a Highland Falls holiday rental?
Book your Highland Falls holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Highland Falls?
In Highland Falls, visitors can explore a variety of attractions that showcase the area's natural beauty and historical significance. One of the main highlights is the United States Military Academy at West Point, located just a short distance away, where you can take guided tours to learn about its rich history and impressive architecture. The nearby Hudson River offers stunning views and opportunities for outdoor activities such as hiking and kayaking.The town itself features charming local shops and eateries, providing a quaint atmosphere to enjoy. For nature enthusiasts, the surrounding Bear Mountain State Park is a fantastic destination, offering hiking trails, picnic areas, and scenic vistas. Additionally, the area is steeped in history, with sites like the West Point Museum, which showcases military artifacts and exhibits.
Can I change or cancel my Highland Falls home rental booking on Vrbo?
To find Highland Falls holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Highland Falls holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas