Montgomery Vacations from $291

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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
Sleep Inn & Suites Middletown - Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Courtyard by Marriott Newburgh Stewart Airport
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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What to do in Montgomery

Montgomery Hotel Deals

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
$89 nightly
The price is $101 total per night from Jul 6 to Jul 7
$101 total
Jul 6 - Jul 7
Total includes taxes and fees
6.4/10 (1,005 reviews)
"The staff were wonderful and friendly. Breakfast was better than anticipated. Floors in the room were sticky, and there were cups, but no coffee pot. Overall good for the price."

Reviewed on Jun 23, 2025

Super 8 by Wyndham Montgomery Maybrook
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 Aug 3 to Aug 4
$129 total
Aug 3 - Aug 4
Total includes taxes and fees
8.6/10 Excellent! (728 reviews)
"Nice, quiet, and clean"

Reviewed on Jun 8, 2025

Holiday Inn Express & Suites Montgomery by IHG
The Kartrite Resort & Indoor Waterpark
The Kartrite Resort & Indoor Waterpark
4 out of 5
555 Resorts World Drive, Monticello, NY
$258 nightly
The price is $291 total per night from Jul 23 to Jul 24
$291 total
Jul 23 - Jul 24
Total includes taxes and fees
8/10 Very Good! (1,532 reviews)
"Wanted more dining options at site itself, not enough dining options outside of property. Nothing is available after 11 onsite or off. Other than that during the day pretty decent"

Reviewed on Jul 1, 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.

Find the Best Montgomery Vacation Packages

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 $291 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.