
Montgomery Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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.

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Price was CA $1,101, price is now CA $908 per person
CA $908
per person
Sep 26 - Oct 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
9.4/10 Exceptional! (789 reviews)
We were stranded in Middletown, NY for 3 days due to a tire issue (waiting on special order tire from Sams Club) and it couldn't have been at a better hotel. Was a very pleasant stay.
Reviewed on Aug. 20, 2025

YO1 Longevity & Health Resorts, Catskills
Price was CA $1,921, price is now CA $1,229 per person
CA $1,229
per person
Sep 26 - Oct 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8/10 Very Good! (469 reviews)
Will definitely be back and want to give a special shout out to Brandon. She was super helpful and very pleasant. Most importantly, my wife loved it and wants to go back…
Reviewed on Aug. 17, 2025

Courtyard by Marriott Newburgh Stewart Airport
Price was CA $1,356, price is now CA $1,002 per person
CA $1,002
per person
Sep 26 - Oct 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.2/10 Very Good! (676 reviews)
The room and outdoor area was great The pool looks like it could use some updating. Had some friends visit and hung out in the garden area which was very nice as well. Fresh fruit and lemon water available daily in lobby.
Reviewed on Aug. 15, 2025

Resorts World Catskills Casino
Price was CA $1,301, price is now CA $969 per person
CA $969
per person
Sep 26 - Oct 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
8.6/10 Excellent! (1,011 reviews)
Nice resort. Few other things to do besides the casino.
Reviewed on Aug. 22, 2025
Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG
2105 Route 208, Montgomery, NY
Fully refundable
The price is CA $146 per night from Sep 21 to Sep 22
CA $146
CA $170 total
Sep 21 - Sep 22
includes taxes & fees
8.6/10 Excellent! (753 reviews)
"Quite pricey for a Holiday Inn in the suburbs. We saved almost $100 booking through Expedia."
Reviewed on Aug. 12, 2025

Super 8 by Wyndham Montgomery Maybrook
207 Montgomery Rd, Montgomery, NY
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Sep 7 to Sep 8
CA $111
CA $125 total
Sep 7 - Sep 8
includes taxes & fees
6.2/10 (1,001 reviews)
"Well done all around. Good value"
Reviewed on Aug. 8, 2025

The Kartrite Resort & Indoor Waterpark
555 Resorts World Drive, Monticello, NY
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Sep 7 to Sep 8
CA $211
CA $327 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,655 reviews)
"It was fun my kids loved it"
Reviewed on Aug. 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.
What to do in Montgomery

BEST LEGOLAND New York 1-Day Tour from New York
CA $251
per adult
Frequently asked questions
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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.