Montgomery Vacations from $378
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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.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport
Price was $484, price is now $378 per person
$378
per person
Dec 2 - Dec 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
5.4/10 (1,016 reviews)
Yes room was clean . Staff Friendly and courteous. Price was right !
Reviewed on Oct 29, 2025
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Save 100% on your flight
Price was $702, price is now $562 per person
$562
per person
Dec 2 - Dec 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
9.4/10 Exceptional! (857 reviews)
great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !
Reviewed on Nov 1, 2025
Super 8 by Wyndham Middletown
Price was $516, price is now $437 per person
$437
per person
Dec 2 - Dec 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
6.2/10 (1,004 reviews)
Everyone was polite, the rooms shower almost didn’t work, the toilet didn’t work, I had to open tank cover to repair for each flush. The keycard worked occasionally on outside doors. Overall we had a nice time.
Reviewed on Oct 27, 2025
Super 8 by Wyndham Montgomery Maybrook
Price was $485, price is now $411 per person
$411
per person
Dec 2 - Dec 9
found 21 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
6.4/10 (1,005 reviews)
The room had dirt accumulated in some corners. There was a used tissue behind the desk. The chemical cleaner that was used had a terrible smell that lasted even though we opened the window. This oder traveled with our clothes after checking out.
Reviewed on Oct 13, 2025
What to do in Montgomery
Taste the Hudson Valley with Gourmet Beacon Food Tour
$135
per adult
Montgomery Hotel Deals
Holiday Inn Express & Suites Montgomery by IHG
2105 Route 208, Montgomery, NY
Fully refundable
$107 nightly
The price is $125 total per night from Nov 23 to Nov 24
$125 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (777 reviews)
Overall good
Reviewed on Oct 25, 2025
Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd, Montgomery, NY
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Nov 27 to Nov 28
$85 total
Nov 27 - Nov 28
Total with taxes and fees
6.2/10 (1,013 reviews)
The room was ok, the carpet did not look very clean, overall, we were able to sleep without any problems.
Reviewed on Oct 23, 2025
Borland House Inn
130 Clinton Street, Montgomery, NY
$114 nightly
The price is $129 total per night from Nov 3 to Nov 4
$129 total
Nov 3 - Nov 4
Total with taxes and fees
9/10 Wonderful! (137 reviews)
We had a great stay at the Bordland House Inn. The Bluebird room was great with nice historical touches that added interest to the room. It was comfy and very relaxing.
Reviewed on Oct 19, 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.
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.