Outlook Vacations from $728

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The Latest Outlook vacation packages

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

The Watford

3 out of 5
Price was $936, price is now $728 per person
$728
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Williston (XWA)
9/10 Wonderful! (515 reviews)
Excellent value! Clean well appointed. Two washers and dryers on each floor but one set was out of order on the second floor. Modest included breakfast. Staff Shay was very friendly and helpful and I’d definitely stay again.

Reviewed on Jul 16, 2026

Bakken Airport XWA Hotel & Studios

Bakken Airport XWA Hotel & Studios

3.5 out of 5
Price was $979, price is now $775 per person
$775
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Williston (XWA)
8.8/10 Excellent! (1,005 reviews)
Very disappointed with property. Very run down. Carpets old and worn, etc. Was expecting a much different experience because of reviews.

Reviewed on Jul 15, 2026

Inn at Hunters Run

Inn at Hunters Run

2.5 out of 5
Price was $1,019, price is now $813 per person
$813
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Williston (XWA)
8.8/10 Excellent! (253 reviews)
Close to North Unit of Theodore Roosevelt National Park but a bit far from the South if you are planning to visit both . Nice to have a kitchen while visiting. Staff members were helpful.

Reviewed on Jul 16, 2026

Fairbridge Inn & Suites Williston Near Airport

Fairbridge Inn & Suites Williston Near Airport

2.5 out of 5
Price was $924, price is now $740 per person
$740
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Williston (XWA)
7.6/10 Good! (668 reviews)
Pool needs some work

Reviewed on Jul 9, 2026

MainStay Suites Watford City - Event Center

MainStay Suites Watford City - Event Center

2.5 out of 5
Price was $952, price is now $768 per person
$768
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Williston (XWA)
8.8/10 Excellent! (134 reviews)
Clean room Good parking Awesome front staff Comfy Cozy Huge room Everyone had space

Reviewed on Jul 4, 2026

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Outlook Hotel Deals

Our cozy, 2 bedroom home offers a blend of comfort and charm!

Our cozy, 2 bedroom home offers a blend of comfort and charm!

Plentywood MT
9.4/10 Exceptional! (11 reviews)
"We had a wonderful stay, perfect for our family. Thanks"

Reviewed on Jun 29, 2026

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Our cozy, 2 bedroom home offers a blend of comfort and charm!
Clean, comfortable cabin. Sleeps 4

Clean, comfortable cabin. Sleeps 4

Plentywood MT
9.8/10 Exceptional! (27 reviews)
"Great little cabin. Our kids loved sleeping in the loft. It’s a well thought out space, especially for a family traveling. Had one small issue which the host resolved right away. Host couldn’t have been better."

Reviewed on Jul 13, 2026

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Clean, comfortable cabin. Sleeps 4
Cedar cabin. Fully equipped. Sleeps 3 comfortably.

Cedar cabin. Fully equipped. Sleeps 3 comfortably.

Plentywood MT
9.6/10 Exceptional! (26 reviews)
"Awesome stay! It was perfect for my work trip! Defiantly would stay here again if i was i town! Thank you!"

Reviewed on Jun 4, 2026

Get rates
Cedar cabin. Fully equipped. Sleeps 3 comfortably.
See all 4 properties in Outlook
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 Outlook Vacation Packages

Outlook Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does an Outlook vacation package cost?
Offering great value package deals from $728 on Expedia, you'll be pleasantly surprised at how much a vacation to Outlook costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Outlook?
If you're hoping to score a cheap Outlook vacation package, consider visiting in November, December and January. You're likely to find lower prices on hotels and airfares during these months — ideal for travelers wishing to save money.
How many days is enough for Outlook?
Generally, a handful of days is enough to see the major sights during your Outlook vacation. However, if you prefer to have some time to rest or take day tours, consider extending your trip.
How to find the best Outlook package deals?
Start your search for an Outlook package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Outlook package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Outlook adventure off to a flying start.
Is it cheaper to book an Outlook vacation as a package?
You can enjoy significant savings on your Outlook retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Outlook?
If you have your Outlook travel dates confirmed, book as soon as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Outlook vacation packages?
If you're anything 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've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Outlook trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.