Shepherd Vacations from $487

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 $837, price is now $487 per person
$487
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Billings (BIL)
8/10 Very Good! (1,349 reviews)
Everything was good and alot of improvments. The hotel is getting better.

Reviewed on Dec 17, 2025

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $916, price is now $674 per person
$674
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Billings (BIL)
9.6/10 Exceptional! (1,147 reviews)
We were upgraded to a corner room which was perfect. The entire staff from bellmen, valet, front desk, housekeeping, Bernie’s, and Ten are always exceptional. The hotel is tastefully decorated - perfect stay!

Reviewed on Dec 16, 2025

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
Downtown Billings
Price was $695, price is now $577 per person
$577
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Billings (BIL)
8.2/10 Very Good! (1,002 reviews)
Great hotel, close to everything downtown.

Reviewed on Dec 11, 2025

Country Inn & Suites by Radisson, Billings, MT

Country Inn & Suites by Radisson, Billings, MT

3 out of 5
Price was $651, price is now $557 per person
$557
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Billings (BIL)
8.2/10 Very Good! (1,000 reviews)
Staff said nothing 😍no greeting

Reviewed on Dec 15, 2025

Big Horn Resort, an Ascend Collection Hotel

Big Horn Resort, an Ascend Collection Hotel

2.5 out of 5
Price was $570, price is now $496 per person
$496
per person
Jan 28 - Feb 1
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Billings (BIL)
7.6/10 Good! (1,001 reviews)
Great rooms and arcade!

Reviewed on Dec 9, 2025

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

Shepherd Hotel Deals

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 $75 total per night from Dec 21 to Dec 22
$75 total
Dec 21 - Dec 22
Total with taxes and fees
7.8/10 Good! (1,154 reviews)
rooms clean, breakfast was good, walls a little thin could hear everything--overall good stay and would stay again

Reviewed on Dec 13, 2025

Days Inn by Wyndham Billings
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Dec 28 to Dec 29
$118 total
Dec 28 - Dec 29
Total with taxes and fees
9.6/10 Exceptional! (321 reviews)
Very clean, great breakfast, and enjoy the convenience of having a drink from the bar right there.

Reviewed on Dec 16, 2025

Hyatt Place Billings
Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
$83 nightly
The price is $94 total per night from Jan 4 to Jan 5
$94 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (1,815 reviews)
Room was wonderful

Reviewed on Dec 15, 2025

Kelly Inn Billings Montana
See all 268 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 $487 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.