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Terry Vacations from $481

Book a Hotel + Flight or Car together to unlock savings

The Latest Terry Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 20 - Aug 24

    The Kempton Hotel + Flight

    Terry
    4 nights
    2.0 star property
    8.6/10 - Excellent (256 reviews)
    "The place is haunted and a train comes by every hour or so blowing its horn (My cousin Vinny) all night long. Impossible to sleep. No refund offered. Left after 3 hours. Went 35 minutes to the road to stay"
    Reviewed June 6, 2026
    Roundtrip • Chicago (CHI) - Glendive (GDV)
    ORD - XWA • 1 stop XWA - ORD • 1 stop
    $530
    $481
    per traveler
    found 1 day ago
    The Kempton Hotel
  • Indoor pool
    Aug 20 - Aug 24

    FairBridge Inn & Suites Glendive + Flight

    Glendive
    4 nights
    3.5 star property
    8.8/10 - Excellent (1,007 reviews)
    "Truthfully we didnt stay here becauae the room we were given was on the 2nd floor with no elevator.i asked for 1st floor. My husband is a disabled veteran and would have had difficulty getting up and down stairs, especially after a recent fall resulting in stitches and a CT scan. Desk clerk said she was unable to switch us. The property looks worn and tired as well. We went across the street to Holiday Inn and forfeited our payment."
    Reviewed July 19, 2026
    Roundtrip • Chicago (CHI) - Glendive (GDV)
    ORD - XWA • 1 stop XWA - ORD • 1 stop
    $640
    $599
    per traveler
    found 1 day ago
    FairBridge Inn & Suites Glendive
  • Free daily continental breakfast
    Aug 20 - Aug 24

    Glendive Lodge + Flight

    Glendive
    4 nights
    3.0 star property
    8.0/10 - Very Good (533 reviews)
    Roundtrip • Chicago (CHI) - Glendive (GDV)
    ORD - XWA • 1 stop XWA - ORD • 1 stop
    $588
    $550
    per traveler
    found 1 day ago
    Glendive Lodge
  • Free daily continental breakfast
    Aug 20 - Aug 24

    Spark by Hilton Glendive + Flight

    Glendive
    4 nights
    3.0 star property
    8.8/10 - Excellent (173 reviews)
    Roundtrip • Chicago (CHI) - Glendive (GDV)
    ORD - XWA • 1 stop XWA - ORD • 1 stop
    $558
    $534
    per traveler
    found 1 day ago
    Spark by Hilton Glendive
  • Exterior
    Aug 20 - Aug 24

    Holiday Inn Express & Suites Glendive by IHG + Flight

    Glendive
    4 nights
    2.5 star property
    9.0/10 - Wonderful (710 reviews)
    "Helpful staff"
    Reviewed July 20, 2026
    Roundtrip • Chicago (CHI) - Glendive (GDV)
    ORD - XWA • 1 stop XWA - ORD • 1 stop
    $732
    $708
    per traveler
    found 1 day ago
    Holiday Inn Express & Suites Glendive by IHG

Terry Hotel Deals

Lobby

The Kempton Hotel

The Kempton Hotel
2.0 star property
< 0.1 mi from Terry
8.6 out of 10, Excellent, (256 reviews)
"The place is haunted and a train comes by every hour or so blowing its horn (My cousin Vinny) all night long. Impossible to sleep. No refund offered. Left after 3 hours. Went 35 minutes to the road to stay"
$65 nightly
The price is $70
Aug 3 - Aug 4
Total with taxes and fees
The Kempton Hotel
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.
See all properties in Terry

Frequently Asked Questions

How much does a Terry vacation package cost?

You'll find cheap prices from $481 on Expedia for your Terry escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Terry costs.

What are the cheapest months to go to Terry?

You can typically find lower prices and better availability in April, May and December. Take a look at our cheap Terry vacation packages and you could land some great off-season deals.

How many days is enough for Terry?

With a well-planned schedule, you can easily hit the top Terry attractions in a few days. But if you prefer to discover hidden gems or take day trips, consider booking your Terry vacation for longer.

How to find the best Terry package deals?

Begin your search for a Terry package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Terry package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Terry adventure off to a flying start.

Is it cheaper to book a Terry vacation as a package?

An Expedia vacation package could land you significant savings when compared to booking hotels and flights separately. Better still, you can personalize your Terry getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

When to book a vacation package to Terry?

If you've got your Terry vacation dates finalized, book as early as you can to bag some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.

Does Expedia offer Book Now, Pay Later Terry vacation packages?

If you're like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Terry trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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