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Terry Vacations from $652

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The Latest Terry Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Aug 26 - Aug 28

    The Kempton Hotel + Flight

    Terry
    2 nights
    2.0 star property
    8.6/10 - Excellent (259 reviews)
    "This historical hotel has a lot of charm. It reminds me of staying in a hostel with the shared bathroom. The rooms are small, but very comfortable. The owners are incredibly friendly and have a lot of knowledge about the area."
    Reviewed July 24, 2026
    Roundtrip • Santa Rosa (STS) - Glendive (GDV)
    STS - GDV • 2 stops GDV - STS • 2 stops
    $658
    $652
    per traveler
    found 1 day ago
    The Kempton Hotel
  • Free daily continental breakfast
    Aug 26 - Aug 28

    Glendive Lodge + Flight

    Glendive
    2 nights
    3.0 star property
    8.0/10 - Very Good (533 reviews)
    "Not the best place to stay"
    Reviewed July 23, 2026
    Roundtrip • Santa Rosa (STS) - Glendive (GDV)
    STS - GDV • 2 stops GDV - STS • 2 stops
    $691
    $681
    per traveler
    found 1 day ago
    Glendive Lodge
  • Indoor pool
    Aug 26 - Aug 28

    FairBridge Inn & Suites Glendive + Flight

    Glendive
    2 nights
    3.5 star property
    8.8/10 - Excellent (1,003 reviews)
    Roundtrip • Santa Rosa (STS) - Glendive (GDV)
    STS - GDV • 2 stops GDV - STS • 2 stops
    $709
    $700
    per traveler
    found 1 day ago
    FairBridge Inn & Suites Glendive
  • Exterior
    Aug 26 - Aug 28

    Holiday Inn Express & Suites Glendive by IHG + Flight

    Glendive
    2 nights
    2.5 star property
    9.0/10 - Wonderful (711 reviews)
    "Clean rooms. Has a great breakfast for any kind of person! Price was a little high for being in a smaller town."
    Reviewed July 24, 2026
    Roundtrip • Santa Rosa (STS) - Glendive (GDV)
    STS - GDV • 2 stops GDV - STS • 2 stops
    $812
    $807
    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, (259 reviews)
"Very unique property, we loved it. With that being said, we went in with expectations appropriate to the stay. We were aware of no bathroom in the room and were okay with this. We didn't ever wait to use the restroom or shower. The property is in pretty good shape considering how long its been in operation. The price was great, the bed was clean and comfortable, and the stay was nice. The decor was wonderful, we really enjoyed it. Very kitschy and cute. If you're looking for a different...
$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 $652 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.