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A grassy field with scattered rocks and distant mountains under a cloudy sky.

Circle Vacations from $1,082

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The Latest Circle Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sep 2 - Sep 7

    The Kempton Hotel + Flight

    Terry
    5 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 • Houston (IAH) - Glendive (GDV)
    IAH - GDV • 2 stops GDV - IAH • 2 stops
    $1,129
    $1,082
    per traveler
    found 4 hours ago
    The Kempton Hotel
  • Daily cooked-to-order breakfast for a fee
    Sep 2 - Sep 7

    Baymont by Wyndham Glendive + Flight

    Glendive
    5 nights
    2.5 star property
    8.4/10 - Very Good (799 reviews)
    "Great stay, especially since they were short staffed. Manager was great, helpful with dinner recommendations. Would stay here again."
    Reviewed July 20, 2026
    Roundtrip • Houston (IAH) - Glendive (GDV)
    IAH - GDV • 2 stops GDV - IAH • 2 stops
    $1,233
    $1,145
    per traveler
    found 4 hours ago
    Baymont by Wyndham Glendive
  • Indoor pool
    Sep 2 - Sep 7

    FairBridge Inn & Suites Glendive + Flight

    Glendive
    5 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 • Houston (IAH) - Glendive (GDV)
    IAH - GDV • 2 stops GDV - IAH • 2 stops
    $1,237
    $1,190
    per traveler
    found 4 hours ago
    FairBridge Inn & Suites Glendive
  • Exterior
    Sep 2 - Sep 7

    Holiday Inn Express & Suites Glendive by IHG + Flight

    Glendive
    5 nights
    2.5 star property
    9.0/10 - Wonderful (710 reviews)
    "Helpful staff"
    Reviewed July 20, 2026
    Roundtrip • Houston (IAH) - Glendive (GDV)
    IAH - GDV • 2 stops GDV - IAH • 2 stops
    $1,355
    $1,316
    per traveler
    found 4 hours ago
    Holiday Inn Express & Suites Glendive by IHG
  • Free daily continental breakfast
    Sep 2 - Sep 7

    Glendive Lodge + Flight

    Glendive
    5 nights
    3.0 star property
    8.0/10 - Very Good (533 reviews)
    Roundtrip • Houston (IAH) - Glendive (GDV)
    IAH - GDV • 2 stops GDV - IAH • 2 stops
    $1,149
    $1,117
    per traveler
    found 4 hours ago
    Glendive Lodge

Circle Hotel Deals

House (4 Bedrooms) | Interior

Charming 'corral Creek Ranch House' in Circle

Charming 'corral Creek Ranch House' in Circle
3.0 star property
12.4 mi from Circle
10.0 out of 10, Exceptional, (1 review)
"It was a cozy house out of town quite. I got kick out of the small cat the welcome us to the house. Be careful the cat liks to seek in lol. "
$261 nightly
The price is $281
Jul 23 - Jul 24
Total with taxes and fees
Charming 'corral Creek Ranch House' in Circle
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 Circle

Frequently Asked Questions

How much does a Circle vacation package cost?

Offering great value package deals from $1,082 on Expedia, you'll be thrilled with how little a vacation to Circle costs! Expedia's packages make travel planning easier and save you more.

What are the cheapest months to go to Circle?

You can usually find lower rates and greater availability in November, December and January. Explore our cheap Circle vacation packages and you could score some great off-season deals.

How many days is enough for Circle?

The ideal duration for your Circle vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to go to all the major sights and explore some hidden treasures along the way.

How to find the best Circle package deals?

Begin your search for a Circle package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Circle package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Circle escape off to a flying start.

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

Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Circle vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Circle?

Score amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Circle escape.

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

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