Billings Vacation Packages

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  • Better together

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

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Top Billings Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,228, price is now CA $728 per person
CA $728
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,492 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,412, price is now CA $3,709 per person
CA $3,709
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,007 reviews)

Freehand New York

Freehand New York

4 out of 5
Manhattan
Price was CA $2,938, price is now CA $1,736 per person
CA $1,736
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,058 reviews)
Decent hotel but the ac in room wasn’t the best it keeps shutting off and there was an error code i called the desk and told the guy he was gonna send someone up but 30 minutes later i called him bsck and said nevermind I figured out how to get it going also the in room fridge is TINY doesn’t fit much at all!! Tv guide wasn’t accurate either channels were off by a few

Reviewed on Jul 31, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $7,779, price is now CA $4,636 per person
CA $4,636
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (689 reviews)
Beautiful hotel. Great experience.

Reviewed on Jul 30, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $3,325, price is now CA $2,050 per person
CA $2,050
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,623 reviews)
Everybody was super friendly, the room was clean and nice and the balcony is a really great little touch. I would suggest booking a room with a balcony. It’s a very nice feature for coffee in the morning and at night to just sit outside. We will be back!

Reviewed on Aug 1, 2026

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Billings Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 9 to Aug 10
CA $150
CA $174 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Arrived at 4:00 PM and waited 15 minutes to get our reserved room. Room had a slightly musty smell."

Reviewed on Aug 1, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Aug 31 to Sep 1
CA $120
CA $139 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Hotel was very clean and well stocked. Breakfast was served with eggs , bacon , sausage and biscuits and gravy which was more than enough to start the new day. Staff was friendly and helpful so I left a good tip in my room for them. Will stay there again"

Reviewed on Jul 30, 2026

Holiday Inn Express Poughkeepsie by IHG
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 31 to Sep 1
CA $164
CA $192 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Biscuit chaud à l'arrivée, accueil sympathique, endroits très propre, lit confortable"

Reviewed on Aug 1, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
See all 661 properties in Billings
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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Frequently asked questions

How much does a Billings vacation package cost?
You'll find cheap prices from CA $728 on Expedia for your Billings break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Billings costs.
What are the cheapest months to go to Billings?
If you're hoping to book a cheap Billings vacation package, consider visiting in January, February and March. You'll typically find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Billings?
The ideal duration of your Billings vacation depends on what you'd like to do. Typically, a few days to a week will give you time to hit all the major sights and explore some hidden spots along the way.
How to find the best Billings package deals?
Begin your search for a Billings package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Billings package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Billings escape underway.
Is it cheaper to book a Billings vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays separately. Better still, you can tailor your Billings trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Billings?
Enjoy incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Billings getaway.
How to plan a trip to Billings?

  1. Choose when to travel: Check your schedule and get packing. Your preferred time of year and the activities on offer will also help you decide when to vacation in Billings.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to experiences and flights. Your hotel will probably be the biggest expense during your trip to Billings.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Billings. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Billings 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.