Montgomery Vacations from $212

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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.
The Crossroads Hotel, Newburgh
YO1 Longevity & Health Resorts, Catskills
Resorts World Catskills Casino
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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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
$111 nightly
The price is $129 total per night from Sep 15 to Sep 16
$129 total
Sep 15 - Sep 16
Total includes taxes and fees
8.6/10 Excellent! (753 reviews)
"Quite pricey for a Holiday Inn in the suburbs. We saved almost $100 booking through Expedia."

Reviewed on Aug 12, 2025

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
$80 nightly
The price is $90 total per night from Aug 20 to Aug 21
$90 total
Aug 20 - Aug 21
Total includes taxes and fees
6.2/10 (1,001 reviews)
"Well done all around. Good value"

Reviewed on Aug 8, 2025

Super 8 by Wyndham Montgomery Maybrook
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
555 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
$216 nightly
The price is $244 total per night from Sep 7 to Sep 8
$244 total
Sep 7 - Sep 8
Total includes taxes and fees
8/10 Very Good! (1,639 reviews)
"limited and expensive food options"

Reviewed on Aug 12, 2025

The Kartrite Resort & Indoor Waterpark
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.

Things to do in and around Montgomery

Montgomery, New York, offers a perfect blend of family-friendly fun and outdoor adventures. Visitors can explore various activities such as walking trails and resort amenities, as well as enjoy shopping at local centers and malls. With its focus on entertainment and outdoor experiences, Montgomery is an ideal destination for a memorable beach vacation or an exciting adventure with loved ones.

Shopping

For a great shopping experience in Montgomery, visit the Galleria at Crystal Run, just 9 miles away, offering entertainment and family vibes. If you're up for a drive, check out Soons Orchards at 12 miles for local goods or Woodbury Common Premium Outlets at 16 miles for outlet shopping.

Recreation

At Ice Time Sports Complex, engage in invigorating ice skating or hockey activities that embrace the energetic sports atmosphere. Thomas Bull Memorial Park offers serene walking trails and picnic areas, perfect for relaxation and rejuvenation amidst nature. For a cultural experience, visit Paramount Theatre for entertaining performances in a charming setting.

Adventure

Experience thrilling motor racing at Orange County Fair Speedway, located 10 miles from Montgomery, where adrenaline and speed meet excitement. Visit Castle Fun Center, 12 miles away, for fun-filled arcade adventures perfect for families. Engage in high-energy paintball battles at Paintball Sports, located 13 miles from Montgomery.

Nightlife

Montgomery offers a charming nightlife with cozy bars and local eateries. Enjoy live music at The Orange County Distillery, or unwind with craft cocktails at The Montgomery Tavern. For a laid-back evening, grab a bite at a nearby diner or explore seasonal events that showcase local talent.

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

Find the best attractions in and around Montgomery

Montgomery, New York, is perfect for families and outdoor enthusiasts, offering a variety of attractions such as urban parks, state parks, and nature reserves. Visitors can enjoy cultural experiences and outdoor activities while exploring local points of interest. Don't miss the chance to visit the Montgomery Museum for a deeper insight into the area's history and culture. Make your trip memorable by embracing the family-friendly and entertainment-focused atmosphere Montgomery has to offer.

  • Orange County Arboretum: Experience the beauty of nature at the Orange County Arboretum, a serene outdoor space perfect for families. Stroll through various themed gardens, enjoy seasonal blooms, and participate in educational programs that connect visitors with the environment.
  • Orange County Farmers Museum: Located 3 miles away, the Orange County Farmers Museum offers a glimpse into the region's agricultural history. Explore exhibits featuring local artifacts and engage with the vibrant culture of farming that has shaped the community.
  • Dia Beacon: About 13 miles from Montgomery, Dia Beacon is a contemporary art museum set in a former factory. Immerse yourself in large-scale installations and thought-provoking exhibitions that push the boundaries of modern art.

Best time to go to Montgomery

The best time to visit Montgomery is dependant 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 RainMostlyAverageSlightly Low
March36.3°F (2.4°C)Light RainMostlyAverageSlightly 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 RainMostlySlightly 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.

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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 $212 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.