Shepherd Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Shepherd Vacation Packages

Shepherd Hotel Deals

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road, Billings, MT
Fully refundable
The price is ₩158,016 per night from Sep 1 to Sep 2
₩158,016
₩176,232 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,726 reviews)
Thank you!
"Great staff! Amazing stay!"

Reviewed on Aug 23, 2025

Kelly Inn Billings Montana
Woodspring Suites Billings

Woodspring Suites Billings

2.5 out of 5
4750 King Ave East, Billings, MT
Fully refundableReserve now, pay when you stay
The price is ₩110,090 per night from Sep 8 to Sep 9
₩110,090
₩124,472 total
Sep 8 - Sep 9
includes taxes & fees
7.8/10 Good! (285 reviews)
"Aside from having to wait for someone to come to the counter for quite some time to check in, the rest of my day was comfortable and met expectations."

Reviewed on Aug 23, 2025

Woodspring Suites Billings
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
1223 Mullowney Ln, Billings, MT
Fully refundableReserve now, pay when you stay
The price is ₩160,424 per night from Sep 20 to Sep 21
₩160,424
₩185,800 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very Good! (1,188 reviews)
"Great place to stay for the night. I saved 135.00 on expedia."

Reviewed on Aug 26, 2025

Billings Hotel and Convention Center
See all 246 properties in Shepherd
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.

Frequently asked questions

How much does a Shepherd vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation to Shepherd costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Shepherd?
If you're looking to score a cheap Shepherd vacation package, consider planning a trip in January, October and December. You'll typically find better prices on hotels and flights during these months — ideal for a budget-friendly break.
How many days is enough for Shepherd?
With a well-planned itinerary, you can easily hit the main Shepherd attractions in a few days. But if you'd like to discover hidden spots or go on day tours, consider booking your Shepherd vacation for longer.
How to find the best Shepherd package deals?
Use Expedia's filters to find some of the best Shepherd package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Shepherd package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Shepherd vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can customize your Shepherd getaway to fit your exact needs. Choose 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 Shepherd?
If you've got your Shepherd vacation dates finalized, book early to grab some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Shepherd?

  1. Choose your dates: What you plan to do in Shepherd and your favorite season can help you decide when to travel.
  2. Set a budget: Consider costs like transportation, flights and meals when working out how much to save for your trip to Shepherd. Then, choose a property that matches your budget, whether that's a wallet-friendly stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the sights and activities you want to experience in Shepherd. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Shepherd vacation package.

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