
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.


The Crossroads Hotel, Newburgh
per person
Apr. 22 - Apr. 27
found 8 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
per person
Apr. 22 - Apr. 27
found 8 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


Homewood Suites Stewart Airport
per person
Apr. 22 - Apr. 27
found 8 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
Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG
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

Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd, Montgomery, NY
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

The Kartrite Resort & Indoor Waterpark
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
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.
Frequently asked questions
What to do in Montgomery

Taste the Hudson Valley with Gourmet Beacon Food Tour
CA $195
per adult
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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.