Montgomery Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, 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.
Newburgh Inn

Newburgh Inn

2 out of 5
per person
Feb. 7 - Feb. 9
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Newburgh (SWF)
5/10 (79 reviews)
There was confusion upon arrival where I was no where to be found in the system, however, the friendly hotel concierge made it work by reaching out to another hotel facility to ensure we no longer had to wait for the room I already paid for. The shower was nice, someone was already previously logged into Netflix (also nice) and we had everything we needed for the short night stay (easy to extend checkout by calling on personal phone due to no landline present).

Reviewed on Dec. 24, 2024

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Mar. 12 - Mar. 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Newburgh (SWF)
7.8/10 Good! (351 reviews)
Somewwhat shabby--broken blinds in the hallway, but generally clean. It would be nice to have a cup or mug, instead of foam disposables for coffee. Excellent value.

Reviewed on Jan. 5, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Mar. 14 - Mar. 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Newburgh (SWF)
8.4/10 Very Good! (1,002 reviews)
It was a pleasant stay. Staff was very nice and helpful.

Reviewed on Dec. 27, 2024

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
Mar. 28 - Apr. 1
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
5.4/10 (1,004 reviews)
Small room with only one lamp, no lights either side of the bed. I went to the lobby and requested another lamp. It was never delivered.

Reviewed on Oct. 30, 2024

Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Mar. 28 - Apr. 1
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Newburgh (SWF)
6.2/10 (1,002 reviews)
Only had a jail juice a tiny muffin and a small bag of goldfish in a btrown paper bag as breakfast

Reviewed on Dec. 6, 2024

Ready to book your vacation to Montgomery?

 

Choose your dates

Montgomery Hotel Deals

Holiday Inn Express & Suites Montgomery, an IHG Hotel
Holiday Inn Express & Suites Montgomery, an IHG Hotel
2.5 out of 5
2105 Route 208, Montgomery, NY
Fully refundable
The price is CA $118 per night from Feb. 2 to Feb. 3
CA $118
CA $138 total
includes taxes & fees
Feb 2 - Feb 3
8.6/10 Excellent! (671 reviews)
Average
"Pancake machine did not work for breakfast, other then that, all was ok."

Reviewed on Jan. 3, 2025

Holiday Inn Express & Suites Montgomery, an IHG Hotel
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 $98 per night from Jan. 20 to Jan. 21
CA $98
CA $110 total
includes taxes & fees
Jan 20 - Jan 21
6.2/10 (1,002 reviews)
A Nice Super 8
"Although this was not my first time at a Super 8, it was my first time at this particular Super 8. The staff were super friendly and the level of customer service I received was truly excellent. Although there was an offer of complimentary breakfast, I think I slept through the fixings, but there ..."

Reviewed on Dec. 12, 2024

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
The price is CA $269 per night from Jan. 9 to Jan. 10
CA $269
CA $396 total
includes taxes & fees
Jan 9 - Jan 10
7.8/10 Good! (1,168 reviews)
"Leah at the ice-cream station, i dint think she likes her job."

Reviewed on Jan. 5, 2025

The Kartrite Resort & Indoor Waterpark
See all 1,179 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

Family Vacations

Frequently asked questions

How much does a Montgomery vacation package cost?
You can grab a vacation package to this popular destination from CA $484 on Expedia. But how much your vacation to Montgomery costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Montgomery?
January, February and March are the best times to search for cheap Montgomery vacation packages. Choosing to travel in less busy periods means you can typically find better prices on flights and accommodations.
How many days is enough for Montgomery?
With a well-planned itinerary, you can easily visit the top Montgomery attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, consider booking your Montgomery vacation for longer.
How to find the best Montgomery package deals?
Begin your search for a Montgomery package deal by entering your preferred travel dates and destination under our “Packages” tab. Then add some filters, like “Property type” and “Popular locations,” to tailor the results to your exact style. You can also sort by “Package discount” and browse offers that come with big savings. If you don’t find the ideal Montgomery package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Montgomery escape off to a flying start.
Is it cheaper to book a Montgomery vacation as a package?
You can enjoy significant savings on your Montgomery retreat by booking a customized vacation package. Click on the “Package” heading, then select your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Montgomery?
If you’re considering a spontaneous Montgomery adventure, check out our last-minute deals that can be booked up to a week before you take off. Don’t want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Montgomery?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to vacation in Montgomery.
  2. Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that could crop up during your trip to Montgomery.
  3. Decide how long to go for: Now that you’re up to speed on Montgomery, you can figure out the ideal length of your vacation. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: Once you’ve settled on your travel dates and duration, book the right Montgomery vacation package for you.

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