Fort Montgomery holiday lettings

We found 150 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Fort Montgomery that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

The friendly city of Fort Montgomery awaits you

The mountains and riverfront provide a pleasant backdrop to your holiday home in Fort Montgomery. Well known for its shopping, skiing and hiking, this welcoming city won't disappoint. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Fort Montgomery

Do you want to find attractions to see during your stay? Venture out of your holiday home and experience everything that Fort Montgomery has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Brotherhood Winery (11.5 mi / 18.5 km)
  • Putnam County Golf Course (12.4 mi / 20 km)
  • Ice Time Sports Complex (14.6 mi / 23.5 km)
  • SplashDown Beach (15.5 mi / 25 km)
  • Mount Peter Ski Area (17 mi / 27.3 km)
  • LEGOLAND® New York (17.2 mi / 27.6 km)

Exploring the natural features in Fort Montgomery

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Fort Montgomery. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Blue Mountain Reservation (5.8 mi / 9.3 km)
  • Storm King State Park (6.3 mi / 10.2 km)
  • Storm King Art Center (7.5 mi / 12 km)
  • Hudson Highlands State Park (7.8 mi / 12.5 km)
  • Arrow Park Lake and Lodge (10.4 mi / 16.7 km)
  • Croton Point Park (11.4 mi / 18.3 km)

Travelling to and around Fort Montgomery

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 12.7 mi (20.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into White Plains, NY (HPN-Westchester County), which is 23.4 mi (37.6 km) away.

Frequently asked questions

What is the best area to stay in Fort Montgomery when booking a holiday rental?
When considering a holiday rental in Fort Montgomery, New York, the area around Bear Mountain State Park is an excellent choice. This picturesque location not only offers stunning views of the Hudson River but also provides a number of outdoor activities such as hiking, cycling, and picnicking. The park is home to the iconic Bear Mountain Inn and features a zoo, making it a delightful spot for families and nature enthusiasts alike.

Another appealing area is close to the West Point Military Academy, which is steeped in history and offers guided tours. The scenic surroundings and the dramatic landscape of the Hudson Highlands provide a unique backdrop for your stay. There are several properties available in both of these areas, suiting various preferences, whether you're looking for a cosy cabin or a spacious family home.
How much does it cost to rent a holiday home in Fort Montgomery?
Prices for holiday rentals in Fort Montgomery 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 Fort Montgomery 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 Fort Montgomery holiday house rentals?
You can find great discounts on house rentals in Fort Montgomery 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 Fort Montgomery ski resort rentals?
For ski resort rentals near Fort Montgomery, travellers should consider the nearby areas of Harriman and Bear Mountain State Parks, which are approximately a short drive away and offer access to various winter sports activities. In Harriman, visitors can find cosy cabins and lodges that provide essential amenities such as fireplaces, kitchens, and outdoor spaces for evening relaxation after a day on the slopes.

In the Bear Mountain area, there are several options for ski-in/ski-out accommodations, with properties often featuring spacious living areas, balconies with mountain views, and easy access to the ski lifts. Many rentals here cater to families or groups, with multiple bedrooms and communal spaces ideal for gathering after a day of skiing.
What is the most popular type of holiday rental accomodation in Fort Montgomery?
In Fort Montgomery, cottages are the most popular type of holiday rental, with several available in this picturesque area. Nestled amidst the scenic landscapes of the Hudson Valley, these cottages offer a charming and rustic experience for visitors. Most properties are equipped with essential amenities such as fully equipped kitchens, comfortable living spaces, and outdoor areas, allowing guests to enjoy the natural surroundings. Ideal for families or couples, these rentals provide a homey atmosphere while being close to local attractions like Bear Mountain State Park and the historic West Point Military Academy.
Are there any family house rentals in Fort Montgomery?
In Fort Montgomery, there are several family-friendly house rentals available, making it a great choice for those travelling with children. This charming area, located near the Hudson River, offers homes that are spacious enough for larger groups. Many properties feature amenities such as fully equipped kitchens, allowing for convenient family meals, and comfortable living areas where everyone can unwind after a day of exploration.
Can I find long-stay holiday rentals in Fort Montgomery?
A long-stay holiday rental in Fort Montgomery 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 Fort Montgomery?
In Fort Montgomery, there are several pet-friendly house rentals available, offering a great option for travellers with furry companions. Many of these properties feature spacious layouts, fully equipped kitchens, and outdoor areas where pets can roam, making them ideal for families or groups. The rentals often provide amenities such as private gardens, decks, or patios, allowing guests to enjoy the natural surroundings.

The area itself is rich in outdoor activities, with easy access to the scenic Hudson Highlands State Park. This park offers various hiking trails that are suitable for pets, providing stunning views of the Hudson River and the surrounding landscape. Additionally, the nearby Bear Mountain State Park is another excellent destination for outdoor adventures with pets, featuring picnic areas, walking paths, and open spaces for dogs to enjoy.
Are there any remote work holiday rentals in Fort Montgomery?
In Fort Montgomery, New York, there are several remote work holiday rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated office spaces, desks, and comfortable chairs, ensuring a productive environment for remote workers. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Fort Montgomery holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Fort Montgomery 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 Fort Montgomery?
In Fort Montgomery, popular rental amenities include kitchenettes equipped with essential appliances such as microwaves and coffee makers, allowing guests to prepare simple meals and enjoy the convenience of dining in. Many rentals also feature blenders, superb for those who enjoy smoothies or other blended beverages. These amenities cater well to travellers looking for a comfortable and self-sufficient stay while exploring the historic and scenic surroundings of the area.
When is the best time to visit Fort Montgomery for a holiday rental?
April is the most popular month to visit Fort Montgomery, as it marks the beginning of the peak season that lasts through to June. During these months, the weather becomes pleasantly mild, with temperatures typically ranging from 10 to 20 degrees Celsius, providing ideal conditions for outdoor activities and sightseeing. Visitors can enjoy exploring the majestic Hudson Highlands and the historic sites within the area, all while taking in the stunning natural beauty that surrounds them.

As spring unfolds, the region comes alive with vibrant blooms, making it a superb time for hiking and leisurely strolls along scenic trails. The comfortable temperatures encourage visitors to immerse themselves in the rich history of Fort Montgomery, including its namesake fort and nearby attractions, such as the West Point Military Academy.

For those looking for a more budget-friendly option, consider visiting in December. While this month may be quieter, it offers its own unique charm, with festive holiday decorations and the chance to experience a serene atmosphere. Winter walks can be particularly peaceful, allowing for reflection amidst the beauty of the season.
How early should I book a Fort Montgomery holiday rental?
Book your Fort Montgomery 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.
Can I change or cancel my Fort Montgomery home rental booking on Vrbo?
To find Fort Montgomery 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 Fort Montgomery 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.

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