Montgomery Vacations from $208
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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 $242, price is now $208 per person
$208
per person
Dec 6 - Dec 8
found 16 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Newburgh (SWF)
5.4/10 (1,005 reviews)
Clean rooms & beds, friendly staff, easy parking
Reviewed on Oct 13, 2025
Sleep Inn & Suites Middletown - Goshen
Price was $765, price is now $592 per person
$592
per person
Nov 25 - Nov 30
found 6 hours ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.4/10 Very Good! (1,010 reviews)
Sink was broken, air conditioning keeps stopping and restarting and it was terrible
Reviewed on Oct 12, 2025
Candlewood Suites Middletown Goshen by IHG
Price was $880, price is now $755 per person
$755
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Houston (HOU) to Newburgh (SWF)
8.4/10 Very Good! (23 reviews)
you could see/feel it was a newly opened hotel
king suite was roomy/comfortable
convenience store, gas and coffee in same area
Reviewed on Aug 25, 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
$95 nightly
The price is $111 total per night from Nov 2 to Nov 3
$111 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (767 reviews)
"We really like the hotel and area very safe"
Reviewed on Sep 14, 2025
Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd, Montgomery, NY
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Nov 3 to Nov 4
$87 total
Nov 3 - Nov 4
Total with taxes and fees
6.2/10 (1,004 reviews)
"Staff Registration person excellent. Aged property-Some furniture needs replacement. Clean bed and bathroom. Typical Super 8 property. Close to I 84. EZ off and on."
Reviewed on Sep 28, 2025
The Kartrite Resort & Indoor Waterpark
555 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
$209 nightly
The price is $236 total per night from Oct 19 to Oct 20
$236 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,746 reviews)
"Sofa on the Room was a bit dusty, but overall was a good hotel and family friendly."
Reviewed on Oct 7, 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.
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.
