Montgomery vacation rentals

We found 123 vacation rentals — enter your dates for availability

Discover a selection of 12 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.

Vacation rentals with weekly discounts - Montgomery

Showing deals for:Apr 17 - Apr 24

Image gallery for Modern, Artsy, & Lofty Log Home

Living area
9.8 out of 10, Exceptional, (123 reviews)
Exceptional
(123 reviews)

Modern, Artsy, & Lofty Log Home

wallkill

22% off
Price is $1,043
$7,302 for 7 nights
All fees included
Modern, Artsy, & Lofty Log Home

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Montgomery

Why visit Montgomery

  • Family-friendly atmosphere: Montgomery offers a welcoming environment perfect for family vacations, with plenty of activities for all ages.
  • Outdoor adventures: Explore numerous parks and preserves, providing ample opportunities for hiking, picnicking, and enjoying nature.
  • Charming accommodations: Choose from a variety of vacation rentals, including cozy cottages and private homes, to enhance your stay.
  • Rich local culture: Experience the vibrant community and historic charm of Montgomery, showcasing its unique heritage.
  • Friendly locals: Enjoy the warm hospitality of Montgomery's residents, making your visit even more memorable.

Popular types of accommodation in Montgomery

Planning a getaway to Montgomery? You're in luck. Our vacation rentals offer a variety of options to suit your needs. Choose from charming houses, cozy condos, and inviting cottages. Whether you're looking for spacious house rentals or serene Montgomery cabins, you'll find the perfect place to unwind and explore. Enjoy transparency, savings, and reassurance as you embark on your Montgomery adventure.

  • Houses: The top choice for visitors in Montgomery, these spacious homes offer a homey atmosphere ideal for families or groups.
  • Condos: A popular option for travelers seeking modern amenities and a communal feel, condos are perfect for a comfortable stay.
  • Cottages: These charming, quaint retreats provide a cozy setting for a relaxing getaway amidst nature.
  • Apartments: Convenient and versatile, apartments offer a great blend of comfort and accessibility for solo travelers or couples.
  • Cabins: These rustic hideaways appeal to those looking for an adventurous escape surrounded by the beauty of the outdoors.**

Top attractions in and around Montgomery

Montgomery, New York, is an ideal vacation spot for families and outdoor enthusiasts alike. With a variety of attractions, including urban parks, state parks, and preserves, visitors can enjoy a blend of culture and nature. Whether you're seeking family fun or outdoor adventures, Montgomery offers a range of experiences that cater to all types of travelers. Get ready to explore the beauty and charm of this delightful destination.

  • Orange County Arboretum: Nestled in Montgomery, this beautiful arboretum features diverse plant species, walking paths, and family-friendly spaces. It's perfect for a leisurely stroll, picnicking, or enjoying nature with loved ones.
  • Orange County Farmers Museum: Located 3 miles away, this museum showcases the rich agricultural history of the region. With engaging exhibits and cultural artifacts, visitors can immerse themselves in local heritage and farming traditions.
  • Dia Beacon: About 13 miles from Montgomery, this contemporary art museum is situated along the Hudson River, featuring large-scale installations and thought-provoking exhibitions from renowned artists, making it a must-visit for art enthusiasts.

Things to do recommended for couples

For a romantic getaway in Montgomery, explore Brotherhood Winery, just 8 miles away, for delightful wine and entertainment. Indulge in relaxation at Jenkinstown Day Spa, 13 miles away. For a touch of luxury, enjoy a round at The Golf Club at Mansion Ridge, located 16 miles from town.

Things to do recommended for families

Families visiting Montgomery, NY, can enjoy exciting activities at Ice Time Sports Complex for sports enthusiasts, relax at Thomas Bull Memorial Park, and have fun at SplashDown Beach, a thrilling waterpark perfect for adventure and family bonding.

Things to do recommended for groups

In Montgomery, groups can savor craft cider at Angry Orchard, enjoy shopping at Woodbury Common Premium Outlets, or experience thrilling races at Orange County Fair Speedway. Each location offers a unique vibe, perfect for creating unforgettable memories together.

*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

When traveling with a group, family, or pets, or if you're planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Montgomery with a group: Think about how many bedrooms you’ll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Montgomery with young kids: Traveling with little ones can be a bit tricky. It's important to prioritize their comfort and safety, as well as access to suitable amenities like a private swimming 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, a family vacation wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Montgomery: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can quickly locate 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 criteria as well.

Where to stay near Montgomery

Montgomery, New York, is an ideal destination for family-friendly vacations, offering a charming blend of historic homes and cozy cottages. Explore the vibrant atmosphere of Montgomery County, where you can find great vacation homes in a perfect location. Enjoy the warmth of friendly locals and indulge in both budget and luxury experiences. Whether you're seeking outdoor adventures or entertainment, Montgomery promises a memorable getaway for everyone.

  • Middletown: Middletown is a vibrant city located 11 miles from Montgomery, offering a delightful blend of family-friendly activities and entertainment. This bustling area is known for its diverse shopping centers and malls, making it an ideal spot for those looking to indulge in retail therapy. Visitors can also enjoy local attractions such as a theme park and scenic lakes, providing a perfect mix of fun and relaxation. Whether you're seeking thrilling rides or a peaceful day by the water, Middletown promises an engaging experience for all.
  • Newburgh: Situated 12 miles from Montgomery, Newburgh is a charming city that captivates visitors with its rich history and outdoor activities. Known for its family-oriented atmosphere, Newburgh features various shopping options and educational venues. The city's proximity to a beautiful lake enhances its appeal, offering opportunities for boating and fishing. Additionally, history buffs will appreciate exploring the local historic sites and visitor centers, making Newburgh a well-rounded destination for both adventure seekers and culture enthusiasts.
  • Beacon: Beacon, located 14 miles from Montgomery, is a picturesque city renowned for its outdoor adventures and family-friendly atmosphere. With a backdrop of stunning mountains and parks, this destination invites visitors to partake in various outdoor activities, including hiking and skiing at local ski fields. The vibrant theater scene adds to the cultural richness of Beacon, making it an exciting place to explore. Whether you’re enjoying a day on the slopes or a relaxing afternoon in the park, Beacon offers endless opportunities for adventure and connection with nature.

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 aiming to save on your upcoming journey? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, if you’re able to book a longer stay, you often unlock significant savings. To discover the ideal 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 find the best options for your needs.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its benefits. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily access properties you've saved or booked in the sections for 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)
  • Goshen Historic Track (9.7 mi / 15.6 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)

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:

  • Algonquin Park (9.3 mi / 14.9 km)
  • Storm King Art Center (11.6 mi / 18.7 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 when booking a vacation rental?
When planning a vacation rental in Montgomery, New York, the historic downtown area is an excellent choice. This charming neighborhood is rich in history and features a variety of well-preserved buildings that reflect its past. Staying here puts you within walking distance of delightful shops, cozy cafes, and a selection of restaurants, making it easy to immerse yourself in the local culture.

Another fantastic option is the area surrounding the Wallkill River. This picturesque location offers beautiful views and opportunities for outdoor activities, such as hiking and fishing. The nearby Wallkill River National Wildlife Refuge is a highlight, providing a serene escape into nature where you can enjoy birdwatching and scenic trails.

Additionally, properties in both these areas tend to be in high demand, offering a range of options from quaint cottages to more spacious homes, making it a popular choice for visitors.
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 areas for renting a beach house in Montgomery?
For renting a beach house in Montgomery, New York, travelers should explore the nearby areas around the Hudson River and local lakes. The scenic waterfront along the Hudson offers charming vacation rentals with beautiful river views and direct access to water activities such as kayaking and fishing. Many properties in this region feature amenities like private docks, outdoor decks, and spacious living areas ideal for family gatherings.

Additionally, the area around Wawayanda State Park, which is a short drive from Montgomery, presents opportunities for lakeside rentals. Expect properties that include amenities such as fire pits, picnic areas, and access to hiking trails in the park, enhancing the outdoor experience. This picturesque park is great for those who enjoy nature and want to combine lake activities with hiking adventures.

Moreover, the historic village of Montgomery itself has a quaint atmosphere, with nearby shops and dining options. Rentals here often include modern conveniences like fully equipped kitchens, air conditioning, and Wi-Fi, ensuring a comfortable stay while exploring the local attractions.
Where are the best Montgomery ski resort rentals?
For ski resort rentals near Montgomery, New York, travelers should consider the nearby areas around the popular ski destination of Mount Peter in Warwick, which is approximately a 30-minute drive away. In Warwick, visitors can find cozy lodges and cabins that cater to winter sports enthusiasts, many of which come equipped with amenities like fireplaces, ski storage, and outdoor hot tubs for post-ski relaxation.

Additionally, the charming town of New Paltz, located about 40 minutes from Montgomery, offers a variety of rental options, including rustic cabins and modern apartments. These properties often feature full kitchens and comfortable living spaces, great for families or groups planning to spend time on the nearby slopes at Mohonk Mountain House or Hunter Mountain, which is a bit further afield.
What is the most popular type of vacation rental accomodation in Montgomery?
In Montgomery, vacation houses are the most popular type of accommodation, with about 10 available in the area. These homes typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or larger groups looking for a comfortable and private stay. Additionally, there are several apartments and cabins, which provide alternative options for travelers. Apartments offer a more compact living space, often including kitchen facilities and cozy living areas, while cabins tend to focus on a rustic experience, often set in more secluded areas for those wanting to connect with nature.
Are there any family house rentals in Montgomery?
In Montgomery, New York, there are several family-friendly house rentals available, making it an excellent choice for families looking to explore the Hudson Valley. The area features spacious properties, often with multiple bedrooms and expansive yards for children to enjoy outdoor activities. Many homes come equipped with full kitchens, allowing families to prepare meals together and enjoy quality time.

Visitors can also find convenient amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. The locale is close to various attractions, including the scenic Walkway Over the Hudson and the charming shops and eateries in the nearby town of New Paltz.
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. This charming area, located in the beautiful Hudson Valley, provides a peaceful setting for relaxation. Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas superb for family gatherings or quiet evenings. Inside, travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes additional features like game rooms or fire pits.
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, New York, there are several pet-friendly house rentals available, making it a great choice for travelers with furry companions. The area offers a mix of charming homes that often feature amenities such as spacious backyards, modern kitchens, and cozy living areas, great for families or groups. Many of these rentals are situated in quiet neighborhoods, providing a peaceful retreat while still being close to local attractions.

For outdoor enthusiasts, Montgomery is near parks and nature areas where pets are welcome, allowing for enjoyable walks and exploration. The nearby Wallkill River offers opportunities for hiking and scenic views, making it a pleasant area for both pets and their owners.
Are there any remote work vacation rentals in Montgomery?
In Montgomery, New York, there are several remote work vacation rentals available, with about 14 options to choose from. This quaint town offers a mix of historic charm and natural beauty, making it a great location for those looking to balance work and leisure. Many of the rentals are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated workspace with desks and chairs, and comfortable environments conducive to productivity.

Travelers can enjoy the picturesque surroundings, with nearby attractions like the Montgomery Park and the Wallkill River, which provide opportunities for outdoor activities during breaks. The local area also boasts quaint shops and dining options, enhancing the overall experience. 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 rental amenities include WiFi, which allows guests to stay connected during their stay. Many vacation rentals feature fully equipped kitchens, ideal for those who prefer to cook their own meals, along with coffee and tea makers for a morning boost. Cozy fireplaces are also common, providing warmth and ambiance during cooler months. Additionally, several rentals boast kitchen islands, offering extra space for meal preparation and socializing.
When is the best time to visit Montgomery for a vacation rental?
The best time to visit Montgomery for a vacation rental is during the summer months, particularly July, when the town comes alive with vibrant activities and events. This peak travel season, spanning from June to August, offers warm temperatures ranging from the mid-70s to low 90s Fahrenheit, great for outdoor exploration and enjoying local festivals.

During this lively period, travelers can indulge in a variety of attractions, from scenic walks along the Hudson River to local farmers' markets brimming with fresh produce. Montgomery's charming atmosphere is enhanced by summer events that highlight the area's rich history and community spirit, making it an ideal destination for travelers.

If you're seeking a more budget-friendly experience, October presents an excellent opportunity to visit while avoiding the summer crowds. This month is great for enjoying the beautiful fall foliage, with the trees showcasing a stunning palette of oranges, reds, and yellows. It's a wonderful time for leisurely strolls and scenic drives, allowing you to appreciate the tranquil beauty of the region.

Ultimately, whether you wish to embrace the bustling summer vibe or savor the peaceful charm of autumn, Montgomery offers delightful experiences year-round.
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?
In Montgomery, New York, visitors can experience firsthand a blend of history and nature. The historic district features charming 19th-century architecture and is home to the Montgomery Village Hall and the nearby Montgomery Cemetery, which is rich in local history. For those interested in outdoor activities, the nearby Wallkill River allows for kayaking and fishing, with scenic views along its banks. The area also offers access to the picturesque Montgomery Park, superb for leisurely strolls or picnics.
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.

More Vacation Ideas