Montgomery Vacations from $220

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Your Montgomery Vacation

The vibrant city of Montgomery is calling. Discover its highlights and hidden gems with a Montgomery vacation package that's customized to you. A trip to Montgomery is a terrific opportunity to sightsee. Be sure to visit big-name attractions such as Angry Orchard, Thomas Bull Memorial Park and Orange County Arboretum. Whoever you're going away with and whether your budget is big or small, your dream Montgomery vacation is just a few clicks away with Expedia.

The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Newburgh Stewart Airport
Buttermilk Falls Inn
The Crossroads Hotel, Newburgh
Beekman Arms Hotel
Sleep Inn & Suites Middletown - Goshen
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Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
2105 Route 208 Montgomery NY
Fully refundable
$82 nightly
The price is $93 total per night from Feb 1 to Feb 2
$93 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (817 reviews)
Very clean and generously sized room. Staff was very courteous and helpful

Reviewed on Jan 21, 2026

Holiday Inn Express & Suites Montgomery by IHG
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
207 Montgomery Rd Montgomery NY
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from Feb 22 to Feb 23
$77 total
Feb 22 - Feb 23
Total with taxes and fees
6.2/10 (1,000 reviews)
Nice place

Reviewed on Nov 18, 2025

Super 8 by Wyndham Montgomery Maybrook
Borland House Inn

Borland House Inn

3 out of 5
130 Clinton Street Montgomery NY
$102 nightly
The price is $116 total per night from Jan 26 to Jan 27
$116 total
Jan 26 - Jan 27
Total with taxes and fees
9.2/10 Wonderful! (147 reviews)
Breakfast was hot and tasty. Staff were all pleasant and accommodating.

Reviewed on Jan 19, 2026

Borland House Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Montgomery Vacation Packages

Things to do in and around Montgomery

Montgomery, New York, is perfect for family-friendly vacations, offering a variety of outdoor adventures and entertainment options. Visitors can enjoy exciting activities like walking trails, relaxing beach vacations, and shopping at local centers. With its blend of fun and education, Montgomery ensures an enjoyable experience for everyone, making it an ideal destination for those seeking adventure and leisure alike.

Shopping

For a delightful shopping experience in Montgomery, visit the Galleria at Crystal Run, just 9 miles away, where you can find a variety of stores and family-friendly activities. If you're up for a drive, check out the Woodbury Common Premium Outlets, located 16 miles away, offering extensive shopping options.

Recreation

Experience the excitement at Ice Time Sports Complex, where you can skate or play hockey in a lively atmosphere. For a cultural escape, head to Paramount Theatre for captivating performances. Enjoy a round of golf surrounded by nature's beauty at West Point Golf Course, perfect for outdoor enthusiasts.

Adventure

Experience the thrill of motor racing at Orange County Fair Speedway, located 10 miles from Montgomery. For family fun, visit Castle Fun Center, an exciting arcade adventure zone 12 miles away. Stay local and enjoy the adventure vibes at the Orange County Tennis Center right in Montgomery.

Nightlife

Experience the vibrant nightlife in Montgomery with a visit to the cozy Montgomery Café for a laid-back vibe. For a livelier scene, check out The Carriage House, where you can enjoy live music and great cocktails. End your night at the local brewery for a taste of craft beer.

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

Find the best attractions near Montgomery

Montgomery, New York, is a charming destination perfect for families and outdoor enthusiasts. With its urban parks, national and state parks, and nature preserves, visitors can enjoy a variety of outdoor activities and cultural experiences. Don't miss the Montgomery Museum for a glimpse into local history. Whether you're seeking adventure or entertainment, Montgomery offers something for everyone to enjoy during their vacation.

  • Dia Beacon: Located 13 miles from Montgomery, Dia Beacon is an impressive contemporary art museum set in a former Nabisco box factory. Its expansive galleries showcase thought-provoking installations and works from renowned artists, all within a unique industrial space that enhances the cultural vibe of the experience.
  • Algonquin Park: Just 9 miles away, Algonquin Park is a beautiful urban park perfect for families. With its lush greenery, playgrounds, and walking trails, it offers a relaxing escape in the city, making it ideal for outdoor activities and quality family time.
  • Orange County Fairgrounds: Located 10 miles from Montgomery, the Orange County Fairgrounds hosts various events throughout the year. With its lively atmosphere, outdoor activities, and family-friendly attractions, it promises fun and excitement for visitors of all ages.

Best time to go to Montgomery

The best time to visit Montgomery is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly SunnyAverageSlightly Low
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 SunnyAverageAverage
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 LowSlightly High
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December32.9°F (0.5°C)Light RainMostly CloudySlightly LowAverage

Tips to save on your trip to Montgomery

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Montgomery.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Montgomery Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
4,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brotherhood Winery, Angry Orchard and Castle Fun Center

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Frequently asked questions

How much does a Montgomery vacation package cost?
You can grab a vacation package to this popular destination from $220 on Expedia. But how much your vacation to Montgomery costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Montgomery?
If you're hoping to score a cheap Montgomery vacation package, consider planning a trip in January, August and December. You're likely to find lower rates on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Montgomery?
The ideal length for your Montgomery vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to visit all the top sights and explore some hidden gems along the way.
How to find the best Montgomery package deals?
Begin your search for a Montgomery package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Montgomery package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Montgomery escape off to a flying start.
Is it cheaper to book a Montgomery vacation as a package?
You can enjoy significant savings on your Montgomery retreat by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Montgomery?
If you're considering a spontaneous Montgomery adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Montgomery vacation packages?
Your Montgomery trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.