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.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
5.4/10 (1,006 reviews)
It was cheaper than others. So my wife booked it online . Heard later from locals a little sketchy safety wise. My room was fine. Breakfast was granola bars and coffee. Hardly a brea fast. Would I stay again ? I would check into others.

Reviewed on Jul. 3, 2025

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
per person
Sep 4 - Sep 8
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
8.2/10 Very Good! (654 reviews)
Does the trick, no more no less. Average.

Reviewed on Jul. 14, 2025

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
5.2/10 (1,001 reviews)
I like my trip is very good

Reviewed on Oct. 25, 2024

Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
5.8/10 (1,008 reviews)
Beds were very comfortable. Staff was nice and helpful. Quiet place. Could offer more for breakfast.

Reviewed on Jul. 8, 2025

Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Newburgh (SWF)
6.4/10 (1,002 reviews)
Great front desk presentation by the team.

Reviewed on Jul. 7, 2025

Ready to book your vacation to Montgomery?

 

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Montgomery Hotel Deals

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 $125 per night from Jul 27 to Jul 28
CA $125
CA $141 total
Jul 27 - Jul 28
includes taxes & fees
6.4/10 (1,005 reviews)
"Great front desk presentation by the team."

Reviewed on Jul. 7, 2025

Super 8 by Wyndham Montgomery Maybrook
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 $130 per night from Aug 10 to Aug 11
CA $130
CA $152 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (733 reviews)
Great beds
"The bed was very comfortable and there were tons of options on TV. The staff was friendly and the location only steps away from a Dunkin', which was great because my only complaint about my stay was the food. Very few options, the pancake maker was broken, and almost no fruit. The tea and coffee ..."

Reviewed on Jul. 10, 2025

Holiday Inn Express & Suites Montgomery by IHG
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 $235 per night from Aug 4 to Aug 5
CA $235
CA $353 total
Aug 4 - Aug 5
includes taxes & fees
8/10 Very Good! (1,554 reviews)
"Excellent"

Reviewed on Jul. 11, 2025

The Kartrite Resort & Indoor Waterpark
See all 1,221 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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What to do in Montgomery

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $181
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

CA $184
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
See all activities in Montgomery

Frequently asked questions

How much does a Montgomery vacation package cost?
Offering excellent value package deals from CA $686 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.