Fort Montgomery Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Fort Montgomery Vacation

The rich history and spectacular views are just the start of the things Fort Montgomery has going for it. Enjoy the very best of this fascinating city your way with a personalized Fort Montgomery vacation package. You'll want to take in the sights during your trip to Fort Montgomery. Drop by leading attractions such as United States Military Academy, Bear Mountain State Park and Michie Stadium. Your ideal Fort Montgomery vacation is a few clicks away. Explore airfares, hotels and more on Expedia for a getaway that's tailored just for you.

Top Fort Montgomery Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,587, price is now CA $991 per person
CA $991
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
Hotel was very clean and staff was great. Would definitely stay here again!

Reviewed on Oct 27, 2026

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

3 out of 5
Southeast Yonkers
Save 100% on your flight
Price was CA $5,063, price is now CA $3,151 per person
CA $3,151
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
3/10 (4 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (706 reviews)

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,176, price is now CA $1,383 per person
CA $1,383
per person
Dec 9 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

Ready to book your vacation to Fort Montgomery?

 

Choose your dates

Fort Montgomery Hotel Deals

Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

2.5 out of 5
1106 Route 9 W Fort Montgomery NY
The price is CA $164 per night from Nov 15 to Nov 16
CA $164
CA $194 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (324 reviews)
"Room was clean. Breakfast and fresh brewed coffee was a nice addition. Comfortable bed"

Reviewed on Oct 27, 2026

Holiday Inn Express West Point by IHG
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
The price is CA $277 per night from Oct 28 to Oct 29
CA $277
CA $470 total
Oct 28 - Oct 29
includes taxes & fees
9.8/10 Exceptional! (149 reviews)
"This place is a blessing. We can’t believe we got to stay here. It’s beyond amazing. I’d give it a 12 rating if allowed. Thank you for hosting us."

Reviewed on Oct 6, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Nov 9 to Nov 10
CA $139
CA $159 total
Nov 9 - Nov 10
includes taxes & fees
7.4/10 Good! (1,502 reviews)
"The first room was very run down and dirty. The walls and door were covered with stains and spots, the chairs had stains and spots on them, and the bed still had hair on it. When we asked about possibly getting a different room the lady working that night was very rude. After some back and forth ..."

Reviewed on Oct 27, 2026

West Gate Inn Nyack
See all 752 properties in Fort 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

Stay near popular Fort Montgomery attractions

Fort Montgomery State Historic Site

You can find out about the history of Fort Montgomery with a stop at Fort Montgomery State Historic Site. Discover the mountain views while you're in the area.
See properties

Frequently asked questions

How much does a Fort Montgomery vacation package cost?
You'll find cheap prices from CA $991 on Expedia for your Fort Montgomery break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Fort Montgomery costs.
What are the cheapest months to go to Fort Montgomery?
If you'd like to book a cheap Fort Montgomery vacation package, consider travelling in February, April and December. You'll generally find better prices on hotels and airfares during these months — perfect for a budget-friendly getaway.
How many days is enough for Fort Montgomery?
Usually, a handful of days is enough to check out the main attractions during your Fort Montgomery vacation. However, if you'd like to have time to chill out or take day trips, consider extending your trip.
How to find the best Fort Montgomery package deals?
Finding a cheap Fort Montgomery package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Fort Montgomery package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Fort Montgomery vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can personalize your Fort Montgomery getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Fort Montgomery?
If you've got your Fort Montgomery travel dates finalized, book as early as you can to score some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Fort Montgomery?

  1. Choose your dates: The things you plan to do in Fort Montgomery and your favourite season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to flights and activities. Your accommodations will likely be the biggest expense during your trip to Fort Montgomery.
  3. Work out your trip length: Think about how much time you want to spend exploring Fort Montgomery. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Fort Montgomery vacation package.

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