Montgomery Vacation Packages

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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.

Top Montgomery Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
May 7 - May 13
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Newburgh (SWF)
8.2/10 Very Good! (611 reviews)
Everything great.. except pool area could use upgrade.

Reviewed on Mar. 10, 2025

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Apr. 22 - Apr. 27
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
7.8/10 Good! (374 reviews)
Property you can tell had been partially renovated but it was little things like a hole in the wall from old thermostat and 2 holds in what used to be a bifold door. Maintenance of the property would go a long way. This was a last minute booking so it’s possible that the room was all that was available. Otherwise our stay was fine and reasonable

Reviewed on Feb. 18, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Apr. 22 - Apr. 27
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
8.4/10 Very Good! (1,005 reviews)
My one complaint - the pillows are terrible. Lumpy and too small. Everything else was terrific.

Reviewed on Mar. 13, 2025

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport

2.5 out of 5
per person
Apr. 22 - Apr. 27
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
9.2/10 Wonderful! (853 reviews)
Excellent place to stay. Very clean, nice rooms and great service.

Reviewed on Mar. 15, 2025

Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
per person
Apr. 22 - Apr. 27
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Newburgh (SWF)
9.2/10 Wonderful! (979 reviews)
I loved the roominess and layout of the room. I loved the handicap accessible. Everything was clean and attractive. Staff was wonderful. Breakfast was nice. Thanks!

Reviewed on Feb. 23, 2025

Ready to book your vacation to Montgomery?

 

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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
The price is CA $138 per night from Mar. 23 to Mar. 24
CA $138
CA $161 total
includes taxes & fees
Mar 23 - Mar 24
8.6/10 Excellent! (690 reviews)
"Customer service"

Reviewed on Feb. 17, 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
The price is CA $96 per night from Mar. 30 to Mar. 31
CA $96
CA $109 total
includes taxes & fees
Mar 30 - Mar 31
6.4/10 (1,004 reviews)
"Awesome staff, very welcoming. The woman at the front desk gave me a plastic fork so I could eat my dinner when I arrived. They were also very helpful when I had a last minute itinerary change. Little noisy due to the truck stop being next door but I know that’s out of their control."

Reviewed on Mar. 11, 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
The price is CA $281 per night from Mar. 20 to Mar. 21
CA $281
CA $409 total
includes taxes & fees
Mar 20 - Mar 21
7.8/10 Good! (1,293 reviews)
"Great"

Reviewed on Mar. 14, 2025

The Kartrite Resort & Indoor Waterpark
See all 1,170 properties in Montgomery
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Montgomery vacation package cost?
You can grab a vacation package to this popular destination from CA $1,051 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?
January, February and March are the best times to search for cheap Montgomery vacation packages. Choosing to travel in less busy periods means you can typically find better prices on flights and accommodations.
How many days is enough for Montgomery?
With a well-planned itinerary, you can easily visit the top Montgomery attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, consider booking your Montgomery vacation for longer.
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.
How to plan a trip to Montgomery?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to vacation in Montgomery.
  2. Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Montgomery.
  3. Decide how long to go for: Now that you’re up to speed on Montgomery, you can figure out the ideal length of your vacation. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you’ve settled on your travel dates and duration, book the right Montgomery vacation package for you.

What to do in Montgomery

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $192
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

CA $195
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
See all activities in Montgomery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.