Shepherd Vacations from $537

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
Price was $1,026, price is now $537 per person
$537
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Billings (BIL)
8/10 Very Good! (1,349 reviews)
A $100 separate card actually charge for incidentals in a place that the room is not worth a $100 and it takes 3-7 says to get your money returned to you after checkout.

Reviewed on Jan 12, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $906, price is now $659 per person
$659
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Billings (BIL)
9.6/10 Exceptional! (1,147 reviews)
Just a pleasant experience

Reviewed on Jan 9, 2026

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
Downtown Billings
Price was $770, price is now $615 per person
$615
per person
Feb 22 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Billings (BIL)
8.2/10 Very Good! (1,002 reviews)
The Hotel room exceeded my expectations. The staff was friendly and attentive. Breakfast could’ve had a few more options but tasted great

Reviewed on Jan 5, 2026

Sleep Inn Billings

Sleep Inn Billings

2.5 out of 5
Price was $718, price is now $595 per person
$595
per person
Feb 18 - Feb 22
found 15 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Billings (BIL)
7.2/10 Good! (1,000 reviews)
I decided to stay several more days and the supervisor during the morning shift was extremely helpful when I booked additional nights. He set the standards for a manager as I noticed him work with his subordinates, in addition to actually cleaning the breakfast buffet area and breaking it down quite impressive! Sgt David McGee U.S Army Infantry Ret/ DV

Reviewed on Jan 10, 2026

Quality Inn

Quality Inn

2.5 out of 5
Price was $689, price is now $578 per person
$578
per person
Feb 18 - Feb 22
found 15 hours ago
Roundtrip non-stop flight included
Spokane (GEG) to Billings (BIL)
8.4/10 Very Good! (1,000 reviews)
The lady upfront during the day was very nice, it was a good stay few things stood out but overall it was a very recommended stay

Reviewed on Jan 9, 2026

Don't see what you're looking for?
See all available trips from Columbus to Shepherd
View all trips

Shepherd Hotel Deals

Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $117 total per night from Jan 30 to Jan 31
$117 total
Jan 30 - Jan 31
Total with taxes and fees
9.6/10 Exceptional! (355 reviews)
Room was spotless and so was the pool.

Reviewed on Jan 14, 2026

Hyatt Place Billings
Days Inn by Wyndham Billings

Days Inn by Wyndham Billings

2 out of 5
843 Parkway Ln Billings MT
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $74 total per night from Jan 17 to Jan 18
$74 total
Jan 17 - Jan 18
Total with taxes and fees
7.8/10 Good! (1,182 reviews)
Clean rooms! Friendly staff.

Reviewed on Jan 13, 2026

Days Inn by Wyndham Billings
Howard Johnson by Wyndham Billings

Howard Johnson by Wyndham Billings

2 out of 5
1345 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $70 total per night from Jan 25 to Jan 26
$70 total
Jan 25 - Jan 26
Total with taxes and fees
6/10 (1,000 reviews)
Good value for the price. Rooms were spacious and clean. Bathrooms could use new grouting to spruce them up. Pool and hot tub (1 was out of order) were nice. The extra charge of $5 to use the water slide was I unexpected! Staff was friendly & accommodating.

Reviewed on Jan 14, 2026

Howard Johnson by Wyndham Billings
See all 272 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.

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Shepherd vacation package cost?
You can grab a vacation package to this top destination from $537 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.

Explore a world of travel with Expedia

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