Montgomery vacation rentals

We found 124 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Montgomery that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, including air conditioning and WiFi. Whatever you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Find out more about Montgomery

Why visit Montgomery

  • Outdoor Adventures: Montgomery is perfect for nature lovers, with urban parks, state parks, and nature preserves offering plenty of outdoor activities.
  • Family-Friendly Attractions: The town features numerous activities suitable for families, ensuring a fun experience for all ages.
  • Charming Downtown: Explore unique shops and local dining options in the vibrant downtown area, adding to the local experience.
  • Diverse Accommodations: From cozy cottages to spacious vacation rentals, Montgomery offers varied lodging options for every budget.
  • Welcoming Community: Enjoy the friendly atmosphere and warm hospitality of the locals, enhancing your visit to this charming town.

Popular types of accommodation in Montgomery

If you're exploring vacation rentals in Montgomery, you're in for a treat. Our most popular options include houses, cozy condos, and charming cottages. Whether you're looking for spacious apartment rentals or comfortable homes with ample bedrooms, Montgomery has something to suit every traveler’s needs. Enjoy the comfort and convenience of our diverse selection of accommodations, ensuring a memorable stay in this vibrant city.

  • Houses: The top choice for visitors to Montgomery, these homes offer spacious accommodations ideal for families or groups looking for a homey experience.
  • Condos: A popular option for those seeking modern amenities and a convenient location, condos are perfect for couples or small families.
  • Cottages: These quaint retreats provide a cozy atmosphere, making them a lovely choice for a peaceful getaway.
  • Apartments: Great for solo travelers or couples, apartments offer flexibility and comfort in a home-like setting.
  • Cabins: For nature enthusiasts, cabins provide a rustic escape, surrounded by the beauty of the outdoors.**

Top attractions near Montgomery

Montgomery, New York, is a fantastic destination for families and outdoor enthusiasts alike, offering a blend of entertainment and natural beauty. Visitors can explore urban parks, national state parks, and nature preserves, making it perfect for those seeking cultural experiences and outdoor adventures. Whether you're looking for family-friendly activities or a chance to connect with nature, Montgomery has a variety of attractions that will create lasting memories.

  • Minnewaska State Park: Nestled in the Shawangunk Mountains, this stunning preserve offers breathtaking views, crystal-clear lakes, and miles of hiking trails. It's perfect for outdoor enthusiasts seeking adventure amidst nature's beauty.
  • Dia Beacon: A contemporary art museum set in a former factory, Dia Beacon showcases large-scale installations and works by renowned artists. The tranquil atmosphere fosters a deep appreciation for modern art and culture.
  • Storm King Art Center: This expansive outdoor sculpture park features impressive installations against a picturesque landscape. Visitors can stroll through beautiful gardens while experiencing the harmonious blend of art and nature.

Things to do recommended for couples

For a romantic getaway in Montgomery, indulge in a round of golf at The Golf Club at Mansion Ridge, just 16 miles away. Enjoy the luxurious atmosphere and stunning views, making it the perfect setting for couples to relax and connect amidst nature.

Things to do recommended for families

Families visiting Montgomery, NY, can enjoy a day at the nearby Orange County Fairgrounds, where kids can experience fun rides and games. You can also explore the scenic trails at the Wallkill River National Wildlife Refuge, perfect for hiking and wildlife watching together.

Things to do recommended for groups

Explore the scenic beauty of Montgomery by visiting the scenic Wallkill River Rail Trail, or enjoy a fun-filled day at the Montgomery Village Park with sports fields and picnic areas. Don't miss the local wineries for tastings and group tours that showcase the region's unique flavors.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Montgomery

If you're traveling with a group, family, pets, or planning an extended stay, it's important to set your priorities when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Montgomery with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Fortunately, on Vrbo, you can easily filter for all these options and more.
  • Traveling to Montgomery with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Montgomery: For many families, a trip wouldn’t feel complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Montgomery: If you're searching for vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Montgomery

Montgomery, New York, offers a delightful mix of family-friendly activities and vibrant atmospheres perfect for a memorable vacation. Explore downtown Montgomery for unique shops and local dining, or venture into nearby cities for diverse experiences. Whether seeking budget-friendly options or a touch of luxury, there’s something for everyone. Enjoy the warmth of friendly locals while experiencing the charm and entertainment this lovely region has to offer.

  • Middletown: Located 11 miles from Montgomery, Middletown offers a vibrant city experience perfect for family outings and entertainment. Visitors can enjoy a variety of activities, including shopping at the local mall and exploring the nearby theme park. The city boasts a lively tourist precinct and a charming central square, making it an ideal hub for dining and leisure. With its blend of urban attractions and family-friendly venues, Middletown is a great destination for those looking to experience the excitement of city life.
  • Newburgh: Situated 12 miles from Montgomery, Newburgh is a city that invites families and outdoor enthusiasts alike to explore its natural beauty and urban charm. The waterfront along the Hudson River offers stunning views and recreational opportunities, such as hiking and picnicking. Visitors can also find a variety of educational attractions and shopping centers, making it easy to spend an entire day enjoying the local culture. Highlights include a picturesque lake and a visitor center that showcases the city’s rich history and landmarks.
  • Beacon: Just 14 miles from Montgomery, Beacon is a city that perfectly blends outdoor adventure with family-friendly fun. Nestled between a lake and mountainous terrain, it offers a range of activities, from scenic hiking trails to skiing in the winter. Beacon is also home to a vibrant arts scene, with theaters and galleries showcasing local talent. The city's parks provide ample space for relaxation and exploration, making it an excellent choice for those looking to enjoy nature and culture in a charming setting.

Best time to go to Montgomery

If you're planning a trip to Montgomery, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly SunnyAverageAverage
February28.8°F (-1.8°C)Light RainMostly CloudyAverageSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyAverageSlightly Low
April48.0°F (8.9°C)Light RainMostly SunnyAverageSlightly Low
May58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
June66.9°F (19.4°C)Light RainMostly SunnySlightly HighAverage
July73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
September63.9°F (17.7°C)Light RainMostly SunnySlightly HighAverage
October52.9°F (11.6°C)Light RainMostly SunnySlightly LowAverage
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December32.9°F (0.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming trip? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make informed choices for a fantastic travel experience.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new trips, pick up right where you left off, or organize your travel plans. You can easily access properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The friendly area of Montgomery awaits your stay

The gardens and surrounding scenery provide a peaceful ambiance to your vacation home in Montgomery. This welcoming and trendy city entices travelers with its shopping and restaurants. 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 Montgomery

Do you want to find top things to see and do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Montgomery has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ice Time Sports Complex (6.7 mi / 10.8 km)
  • Brotherhood Winery (7.6 mi / 12.3 km)
  • LEGOLAND® New York (11.2 mi / 18 km)
  • Robibero Winery (13.5 mi / 21.7 km)
  • Benmarl Vineyards and Winery (13.9 mi / 22.4 km)
  • SplashDown Beach (17.2 mi / 27.7 km)

Exploring the natural landscape of Montgomery

Whether you're an active traveler or just want to spend some time taking in the scenery, Montgomery is a great place to spend some time outside. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Orange County Arboretum (3.8 mi / 6.2 km)
  • Algonquin Park (9.3 mi / 14.9 km)
  • Sam's Point Preserve (12 mi / 19.3 km)
  • The Rock Sports Complex (12.8 mi / 20.5 km)
  • Lake Minnewaska Beach (13.8 mi / 22.2 km)
  • Shawangunk Mountains (14 mi / 22.5 km)

How to get to and around Montgomery

The nearest airport is in Stewart Intl. Airport (SWF), located 8 mi (12.9 km) from the city center.

Frequently asked questions

What is the best area to stay in Montgomery, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Montgomery, New York, the area surrounding the historic downtown is an excellent choice. This charming neighborhood offers a delightful mix of small-town character and modern conveniences. Here, you can explore the picturesque streets lined with unique shops, cozy cafes, and local eateries that add to the town's vibrant setting.

A standout attraction in this area is the Montgomery Village Park, where you can enjoy green spaces, walking trails, and playgrounds—superb for a leisurely afternoon. Additionally, the nearby Orange County Farmers Museum provides a fascinating glimpse into the region's agricultural history and hosts various events throughout the year.

There are several vacation rental options within this neighborhood, suiting different preferences and group sizes. Staying in downtown Montgomery allows easy access to these attractions while providing a welcoming and family-friendly environment.
How much does it cost to rent a vacation home in Montgomery?
Prices for vacation rentals in 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 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 Montgomery vacation house rentals?
You can find great discounts on house rentals in 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 Montgomery ski resort rentals?
For skiing near Montgomery, travelers should consider properties in the nearby area of Mountain Creek, located about 30 minutes away. This ski resort offers a variety of winter sports and activities, making it a popular destination for skiing enthusiasts. In the nearby town of Vernon, visitors can find a range of cozy cabins and lodges that cater to different group sizes. Many rentals come equipped with essential amenities, such as full kitchens, fireplaces, and communal spaces for relaxing after a day on the slopes.

Additionally, the surrounding area boasts charming inns and lodges that often feature hot tubs or saunas, providing a great way to unwind. Many accommodations in Vernon are conveniently located near local dining options and shops, enhancing the overall experience for travelers. For those looking to explore the outdoors beyond skiing, nearby hiking trails offer scenic views and opportunities for winter activities like snowshoeing or sledding.
What is the most popular type of vacation rental accomodation in Montgomery?
In Montgomery, vacation houses are the most popular type of rental, with around 11 available throughout the area. These houses typically offer spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing or entertaining. For those seeking a more compact option, several apartments and cabins are also available, providing a cozy atmosphere with essential amenities.
Are there any family house rentals in Montgomery?
In Montgomery, New York, there are several family-friendly house rentals available, making it an inviting destination for those traveling with kids. The area features charming neighborhoods close to local parks and recreational facilities superb for outdoor activities. Many of these homes come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces for children to enjoy.

Visitors can expect amenities like Wi-Fi, air conditioning, and comfortable furnishings to enhance their stay. The nearby scenic spots, such as the beautiful Wallkill River and various hiking trails, offer opportunities for family adventures.
Can I rent a vacation home with a pool or hot tub in Montgomery?
In Montgomery, New York, there are several vacation homes available for rent that feature pools and hot tubs, providing guests with a relaxing retreat. The area offers a mix of charming properties situated in scenic neighborhoods, ideal for families or groups looking to enjoy a getaway. Many of these rentals come equipped with private pools, spacious outdoor areas for lounging, and hot tubs superb for unwinding after a day of exploration. Additionally, amenities such as fully equipped kitchens, barbecue grills, and ample living space enhance the comfort and enjoyment of your stay. Find your rental in Montgomery with a pool or a hot tub.
Can I find long-stay vacation rentals in Montgomery?
A long-stay vacation rental in Montgomery is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Montgomery?
In Montgomery, travelers can find several pet-friendly house rentals that cater to both families and their furry companions. Many of these homes come equipped with spacious yards, allowing pets to roam freely, and some even feature amenities like outdoor seating areas, fire pits, and fully stocked kitchens for convenient meal preparation.

The area is surrounded by beautiful landscapes, making it ideal for outdoor activities with pets. Nearby parks and trails provide ample opportunities for walks and playtime, ensuring both guests and their pets can enjoy the natural beauty of the region.
Are there any remote work vacation rentals in Montgomery?
In Montgomery, New York, there are several remote work-friendly vacation rentals available, with around 14 options to choose from. These properties are well-suited for those looking to balance work and leisure, featuring amenities such as free Wi-Fi, dedicated desk spaces, and comfortable chairs to enhance productivity. Many rentals also offer additional conveniences like printers, ensuring a functional workspace for remote professionals.

The area itself is known for its picturesque landscapes and historical significance, providing a peaceful backdrop for work and relaxation. Nearby attractions include scenic parks and charming local shops, making it easy to take breaks and explore the local culture. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Montgomery vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Montgomery with parking available—perfect for families or travelers 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 Montgomery?
In Montgomery, popular vacation rental amenities include a well-equipped kitchen, which allows guests to prepare their own meals while enjoying the comforts of home. Many rentals also feature a cozy fireplace, great for creating a warm atmosphere during cooler evenings. For those needing to stay productive, a desk is often provided, making it convenient for work or planning activities. Additionally, travelers will appreciate the proximity to golf courses, enhancing the outdoor recreational experience in the area.
When is the best time to visit Montgomery for a vacation rental?
The peak season for vacation rentals in Montgomery typically spans from June to August, with July being the most popular month for travelers. During this vibrant summer period, visitors can enjoy a variety of outdoor activities, including hiking, biking, and exploring the scenic Hudson Valley. The warm temperatures, often ranging from the mid-60s to the low 80s Fahrenheit, create a comfortable environment for sightseeing and enjoying the local parks.

If you're looking for a more tranquil experience, consider visiting in December. This month offers a unique charm as the town embraces the holiday spirit, with festive decorations and local events that provide a cozy atmosphere. While December may be quieter, it's a wonderful time to explore Montgomery's quaint shops and enjoy seasonal festivities.

Ultimately, your choice of when to visit Montgomery for a vacation rental will depend on whether you're drawn to the lively summer scene or the peaceful charm of the winter season.
How early should I book a Montgomery vacation rental?
Book your Montgomery vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Montgomery, New York, United States of America?
In Montgomery, New York, visitors can explore a variety of attractions that highlight the area's history and natural beauty. The historic district features charming streets lined with 19th-century homes and buildings, offering a glimpse into the town's past. The Orange County Farmers Museum is a popular spot where guests can learn about local agricultural history and enjoy seasonal events.

For outdoor enthusiasts, the nearby Wallkill River offers opportunities for kayaking and fishing, while the scenic landscapes of the Shawangunk Mountains provide stunning views and hiking trails. Additionally, the area is home to several parks, including Montgomery Park, which features playgrounds and sports facilities, making it a great spot for families.

Wine lovers can visit local vineyards in the surrounding regions, adding to the appeal of this quaint town.
Can I change or cancel my Montgomery home rental booking on Vrbo?
To find Montgomery vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 Montgomery vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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