Shepherd Vacations from $360
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Your Shepherd Vacation
The adventure-filled city of Shepherd is calling. Discover its hot spots and hidden treasures with a Shepherd vacation package that's tailored to you. Every trip to Shepherd should include some sightseeing. Town & Country Lanes and Lounge is a popular place to kick things off. A couple of quick clicks is all it takes to build your dream Shepherd vacation on Expedia.
The Latest Shepherd vacation packages
Price found within the past 48 hours. Click for updated prices.
Western Executive Inn
West End
$360
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
8/10 Very Good! (467 reviews)
I stay there every time I come to Billings and that is several times a year. Price is okay. Room was clean, A/C was great, very good parking, no charge and staff were very good.
Reviewed on Sep 22, 2026
avid Hotels Billings West by IHG
Shiloh
$435
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Portland (PDX) to Billings (BIL)
9.4/10 Exceptional! (509 reviews)
The hotel was extremely clean. Very nice property. HOWEVER…. The guy who checked us in was awful. He did not greet us at all. Barely said a word. Handed us our key with no instructions. He didn’t tell us about breakfast, wifi of check out. Literally nothing. Come on people, you are in customer service.
Reviewed on Sep 21, 2026
Shepherd Hotel Deals
Kelly Inn Billings Montana
5610 South Frontage Road Billings MT
Fully refundable
$103 nightly
$115 total
Oct 7 - Oct 8
Total with taxes and fees
8.8/10 Excellent! (2,080 reviews)
"The room, facility, & grounds were clean, well landscaped, & used beautiful artwork of the area. Staff was extremely friendly & helpful from the front desk to housekeeping to hospitality. The saying “you get what you pay for” does not apply here because although economically priced, you get so much ..."
Reviewed on Sep 23, 2026
Billings Hotel and Convention Center
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
$124 nightly
$137 total
Sep 29 - Sep 30
Total with taxes and fees
8.2/10 Very Good! (1,860 reviews)
"Was great for our evening."
Reviewed on Sep 22, 2026
Western Executive Inn
3121 King Ave W Billings MT
Fully refundableReserve now, pay when you stay
$64 nightly
$73 total
Oct 2 - Oct 3
Total with taxes and fees
8/10 Very Good! (520 reviews)
"I stay there every time I come to Billings and that is several times a year. Price is okay. Room was clean, A/C was great, very good parking, no charge and staff were very good."
Reviewed on Sep 22, 2026
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 Shepherd Vacation Packages
Shepherd Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Logan Intl. Airport (BIL) |
Population | 520 |
Top Sights | Lake Elmo State Park, Town & Country Lanes and Lounge and MetraPark |
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Frequently asked questions
How much does a Shepherd vacation package cost?
You can grab a vacation package to this top destination from $360 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?
Usually, a handful of days is enough to check out the major sights during your Shepherd vacation. However, if you'd like to have more time to chill out or go on day trips, consider extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Shepherd vacation packages?
Your Shepherd break is meant to be an escape from your daily routine, not a source of money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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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.
