Montgomery Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Price was CA $613, price is now CA $540 per person
CA $540
per person
Apr 27 - Apr 30
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (712 reviews)
Older room with chemical cleaning solution smell
Reviewed on Mar 24, 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $854, price is now CA $787 per person
CA $787
per person
May 9 - May 12
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (985 reviews)
Best hotel in town. Clean clean smoke free hotel
Reviewed on Feb 27, 2026
The Lagrange Inn & Extended Stay
Price was CA $795, price is now CA $733 per person
CA $733
per person
May 8 - May 11
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Newburgh (SWF)
9.4/10 Exceptional! (13 reviews)
The room was freezing cold for about a half hour when we got there but the heater worked well and eventually it warmed up. Room was large and clean. Parking was right in front of room. Wish the room had a full length mirror. People travel when they have an event to go to and we like to see how we look. The bathroom mirror sort of tilts down for a bit of an outfit check but a full length would have been great. Bed was comfortable and bedding was really nice! Guy who runs the place was very nice! Easy check in with digital code and no need for a front desk visit. We would stay again if in the area.
Reviewed on Jan 8, 2026
Montgomery Hotel Deals
Holiday Inn Express & Suites Montgomery by IHG
2105 Route 208 Montgomery NY
Fully refundable
The price is CA $141 per night from Apr 6 to Apr 7
CA $141
CA $159 total
Apr 6 - Apr 7
includes taxes & fees
8.8/10 Excellent! (837 reviews)
The bed was upside down. We realized it the next day it felt super hard.
Reviewed on Mar 24, 2026
Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd Montgomery NY
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Apr 1 to Apr 2
CA $108
CA $122 total
Apr 1 - Apr 2
includes taxes & fees
Borland House Inn
130 Clinton Street Montgomery NY
The price is CA $141 per night from Mar 30 to Mar 31
CA $141
CA $164 total
Mar 30 - Mar 31
includes taxes & fees
9.2/10 Wonderful! (157 reviews)
What a wonderful experience staying at the Borland House is! With the quaint, homey feeling of the whole house, to the kindness of the staff. Your stay will absolutely be lovely. Ample towels are provided for the private, spacious bathroom. Very comfortable bedding and well appointed decorations ...
Reviewed on Mar 22, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
