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.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
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

YO1 Longevity & Health Resorts, Catskills

4 out of 5
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

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
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

Resorts World Catskills Casino

4.5 out of 5
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

Epic Architectural Masterpiece w Views hot tub

Epic Architectural Masterpiece w Views hot tub

2 out of 5
Price was CA $4,032, price is now CA $3,366 per person
CA $3,366
per person
Sep 26 - Oct 1
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
No reviews

Ready to book your vacation to Montgomery?

 

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Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

2.5 out of 5
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

Holiday Inn Express & Suites Montgomery by IHG
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
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

Super 8 by Wyndham Montgomery Maybrook
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
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

The Kartrite Resort & Indoor Waterpark
See all 1,211 properties in Montgomery
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.
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What to do in Montgomery

BEST LEGOLAND New York 1-Day Tour from New York

BEST LEGOLAND New York 1-Day Tour from New York

CA $251
per adult
BEST LEGOLAND New York 1-Day Tour from New York
See all activities in Montgomery

Frequently asked questions

How much does a Montgomery vacation package cost?
Offering excellent value package deals from CA $908 on Expedia, you'll be surprised at how little a vacation to Montgomery costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Montgomery?
If you're hoping to score a cheap Montgomery vacation package, consider travelling in January, February and March. You'll usually find lower rates on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Montgomery?
When planning your Montgomery vacation, a few days will be enough to see the top spots. Be sure to check out Orange County Farmers Museum — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some tours from Montgomery.
How to find the best Montgomery package deals?
Finding a cheap Montgomery package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Montgomery package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Montgomery vacation as a package?
You can enjoy significant savings on your Montgomery escape by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Montgomery?
If you're planning an impromptu Montgomery trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Montgomery?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Montgomery.
  2. Budget wisely: In addition to the price of your accommodations, you'll need to consider other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Montgomery.
  3. Decide your trip length: Consider how long you want to spend discovering Montgomery. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Montgomery vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.