Circle Vacations from $469

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The Latest Circle vacation packages

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

The Kempton Hotel

2 out of 5
Price was $504, price is now $469 per person
$469
per person
Aug 21 - Aug 25
just found
Roundtrip non-stop flight included
Chicago (CHI) to Glendive (GDV)
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 on Jun 6, 2026

Baymont by Wyndham Glendive

Baymont by Wyndham Glendive

2.5 out of 5
Price was $1,010, price is now $855 per person
$855
per person
Sep 20 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Glendive (GDV)
8.4/10 Very Good! (790 reviews)
Great stay

Reviewed on Jul 7, 2026

FairBridge Inn & Suites Glendive

FairBridge Inn & Suites Glendive

3.5 out of 5
Price was $656, price is now $569 per person
$569
per person
Aug 21 - Aug 25
just found
Roundtrip non-stop flight included
Chicago (CHI) to Glendive (GDV)
8.8/10 Excellent! (1,005 reviews)
Perfect for a place to stay when traveling. Clean rooms and friendly staff.

Reviewed on Jul 9, 2026

SureStay by Best Western Glendive Yellowstone River

SureStay by Best Western Glendive Yellowstone River

3 out of 5
Price was $900, price is now $794 per person
$794
per person
Sep 20 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Glendive (GDV)
8.4/10 Very Good! (552 reviews)
Property was clean and convenient but nothing special stood out. Staff was friendly but desk staff were required to perform.other.tasks.andnthusnwerw not readily available. Breakfast was simple but sufficient.

Reviewed on Jul 7, 2026

Glendive Lodge

Glendive Lodge

3 out of 5
Price was $730, price is now $668 per person
$668
per person
Aug 14 - Aug 17
found 24 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Glendive (GDV)
8/10 Very Good! (513 reviews)
We just needed a place to sleep on our road trip, and this fit the bill. Nothing fancy. I was not impressed by the AC though. It was SO LOUD! I finally turned it off after an hour and a half of it roaring without stopping. Also, our room was right next to the mechanic's shop, so we got woken up by him drilling into things at 6am. Not my favorite.

Reviewed on Jul 9, 2026

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Circle Hotel Deals

Rustic 2-bedroom house in fabulous Circle, MT.

Rustic 2-bedroom house in fabulous Circle, MT.

Circle MT
$198 nightly
The price is $213 total per night from Jul 11 to Jul 12
$213 total
Jul 11 - Jul 12
Total with taxes and fees
9.4/10 Exceptional! (13 reviews)
"Everything as stated. Thank you! Had a great stay!"

Reviewed on Jul 3, 2026

Rustic 2-bedroom house in fabulous Circle, MT.
Centrally located in Circle, MT with 3 comfortable bedrooms!

Centrally located in Circle, MT with 3 comfortable bedrooms!

Circle MT
$227 nightly
The price is $245 total per night from Jul 13 to Jul 14
$245 total
Jul 13 - Jul 14
Total with taxes and fees
10/10 Exceptional! (8 reviews)
"Perfect place for our one-night stay."

Reviewed on Jul 6, 2026

Centrally located in Circle, MT with 3 comfortable bedrooms!
Charming 'Corral Creek Ranch House' in Circle

Charming 'Corral Creek Ranch House' in Circle

Circle MT
$264 nightly
The price is $285 total per night from Jul 11 to Jul 12
$285 total
Jul 11 - Jul 12
Total with taxes and fees
6/10 (2 reviews)
"Perfect location for our needs."

Reviewed on Nov 15, 2025

Charming 'Corral Creek Ranch House' in Circle
See all 20 properties 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.

Find the Best Circle Vacation Packages

Circle Essential Information

Language
English
Currency
U.S dollars
Population
610
Max Temp Winter
25ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Circle vacation package cost?
Offering great value package deals from $469 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.

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