Highland Falls holiday rentals

We found 381 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:8 Jan - 15 Jan

Hallway with pocket doors on main floor
View of the dining room
Original mahogany wood work and French Chandliers though out the house
Walk way to back yard from side of the house
Exceptional
(18 reviews)

Stunning historic Victorian house in Newburgh. Pet friendly

Newburgh

21% off
AU$8,030
for 7 nights, 1 home
AU$1,147 per night
includes taxes & fees
Stunning historic Victorian house in Newburgh. Pet friendly
Dining
Interior
Private kitchen
Beautiful back deck for summertime gatherings!
Exceptional
(56 reviews)

Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums

Marlboro

8% off
AU$3,028
for 7 nights, 1 room
AU$433 per night
includes taxes & fees
Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums
Living area
Pool
Interior
Room
Wonderful
(17 reviews)

complete privacy vacation home [private pool]

Newburgh

12% off
AU$8,694
for 7 nights, 1 home
AU$1,242 per night
includes taxes & fees
complete privacy vacation home [private pool]
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
(20 reviews)

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

Milton

16% off
AU$3,603
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Historic 4 BR Family Home Near Buttermilk Falls & Hudson River, on 5 Acres
Property grounds
Exterior
Interior
Terrace/patio
Exceptional
(47 reviews)

Cosy lakefront cottage in Hudson Valley

Walden

7% off
AU$2,414
for 7 nights, 1 cottage
AU$345 per night
includes taxes & fees
Cosy lakefront cottage in Hudson Valley
Pool
Living area
Outdoor dining
Dining
Exceptional
(17 reviews)

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

Harriman

11% off
AU$6,405
for 7 nights, 1 home
AU$915 per night
includes taxes & fees
The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC
Exterior
Private kitchen
Interior
Dining
Exceptional
(17 reviews)

Amazing Home Near West Point, Shopping, Skiing and Legoland

Monroe

7% off
AU$4,434
for 7 nights, 1 home
AU$633 per night
includes taxes & fees
Amazing Home Near West Point, Shopping, Skiing and Legoland
Private kitchen
Living area
Exterior
Room
Exceptional
(19 reviews)

Escape NYC to the Withers Mansion a Grand Hudson Valley Retreat for Large Groups

Newburgh

16% off
AU$4,571
for 7 nights, 1 home
AU$653 per night
includes taxes & fees
Escape NYC to the Withers Mansion a Grand Hudson Valley Retreat for Large Groups
Living area
Exterior
Interior
Property grounds
Exceptional
(13 reviews)

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Hopewell Junction

8% off
AU$2,027
for 7 nights, 1 home
AU$290 per night
includes taxes & fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Private entrance to apt.
Main house. Apt is downstairs to the left.
Private kitchen
Dining
Exceptional
(22 reviews)

Lower level unit in Spectacular Log Home Estate

Marlboro

12% off
AU$2,107
for 7 nights, 1 apartment
AU$301 per night
includes taxes & fees
Lower level unit in Spectacular Log Home Estate
View of kitchen from living room
Covered lakeside gazebo
Breakfast nook
Memorable sunsets
Exceptional
(48 reviews)

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh

8% off
AU$4,873
for 7 nights, 1 home
AU$696 per night
includes taxes & fees
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Living area
Property grounds
Outdoor dining
Exterior
Exceptional
(9 reviews)

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

Marlboro

11% off
AU$2,119
for 7 nights, 1 home
AU$303 per night
includes taxes & fees
Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.
Interior
Living area
Room
Dining
Exceptional
(29 reviews)

Hudson River Retreat

Newburgh

8% off
AU$2,295
for 7 nights, 1 apartment
AU$328 per night
includes taxes & fees
Hudson River Retreat
Dining
Interior
Interior
Outdoor dining
Exceptional
(23 reviews)

Peekskill Carriage House Downtown Studio

Peekskill

8% off
AU$2,213
for 7 nights, 1 home
AU$316 per night
includes taxes & fees
Peekskill Carriage House Downtown Studio
Privacy on the hill
View from Las Mananitas Mexican restaurant in Brewster
Dining
Interior
Exceptional
(120 reviews)

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel

8% off
AU$3,005
for 7 nights, 1 home
AU$429 per night
includes taxes & fees
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Open floor kitchen, LR, and DR, with panoramic view of lake.
Breathtaking View, Situated on Orange Lake
Front of house. Lake in back.
Through the front door to spectacular lake beauty
Exceptional
(331 reviews)

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

Newburgh

8% off
AU$4,726
for 7 nights, 1 home
AU$675 per night
includes taxes & fees
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Exterior
Outdoor spa tub
Private kitchen
Room
Exceptional
(15 reviews)

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

Cornwall

11% off
AU$2,909
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Private kitchen
Property grounds
Private kitchen
Living area
Excellent
(62 reviews)

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Hopewell Junction

8% off
AU$3,514
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

  • 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, laundry, 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. 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:

  • West Point Golf Course (2 mi / 3.2 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)
  • Fishkill Ridge (9.7 mi / 15.7 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Highland Falls holiday homes prices shown on Stayz?
Stayz 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.
Are there any Highland Falls holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Highland Falls holiday homes?
You can find great discounts on holiday homes in Highland Falls on Stayz, 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.
Can I change or cancel my Highland Falls holiday home booking on Stayz?
To find Highland Falls holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Highland Falls?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Highland Falls holiday home?
Book your Highland Falls holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Highland Falls?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Highland Falls to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas