Shepherd Vacations from $656
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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.
Billings Hotel and Convention Center
Southwest Corridor
$656
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
8.2/10 Very Good! (1,814 reviews)
Would never stay at this hotel again. Terrible condition, holes in the wall, rooms stink! Looks like nothing has been touched in 40 years. On top of that they expect you to pay for breakfast. Gross outdated property.
Reviewed on Aug 30, 2026
Rock Creek Resort
$822
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.6/10 Exceptional! (174 reviews)
This place is fabulous. The view of Rock Creek from our balcony was lovely. Food was great. You will get a great MT mountain feel when staying here.Red Lodge is a nice little town to experience.
Reviewed on Aug 30, 2026
My Place Hotel - Billings, MT
Southwest Corridor
$988
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Wichita Falls (SPS) to Billings (BIL)
8.8/10 Excellent! (1,028 reviews)
It would have been helpful when we checked in for them to let us know that paper plates, etc. were available. We didn't know that the room with a full kitchenette had zero dishes. Otherwise this was nice, clean and comfortable.
Reviewed on Aug 30, 2026
Shepherd Hotel Deals
Kelly Inn Billings Montana
5610 South Frontage Road Billings MT
Fully refundable
$102 nightly
$114 total
Sep 20 - Sep 21
Total with taxes and fees
Billings Hotel and Convention Center
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
$124 nightly
$137 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,811 reviews)
"Would never stay at this hotel again. Terrible condition, holes in the wall, rooms stink! Looks like nothing has been touched in 40 years. On top of that they expect you to pay for breakfast. Gross outdated property."
Reviewed on Aug 30, 2026
Northern Hotel
19 North Broadway Billings MT
$178 nightly
$196 total
Sep 6 - Sep 7
Total with taxes and fees
9.6/10 Exceptional! (1,280 reviews)
"It's always so nice staying at The Northern - the staff are always smiling and kind, and very professional. The rooms are very clean, and they have everything you'll need. I love Bernie's Diner for breakfast - such a great spot in downtown Billings!"
Reviewed on Aug 31, 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 $656 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.
