Shepherd Vacations from $330

Book a Hotel + Flight or Car together to unlock savings

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.
Quality Inn

Quality Inn

2.5 out of 5
Price was $402, price is now $330 per person
$330
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
8.4/10 Very Good! (1,000 reviews)
Rooms were clean. Pool area was clean and comfortable

Reviewed on Dec 12, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
Price was $712, price is now $434 per person
$434
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
8/10 Very Good! (1,349 reviews)
Check in was super quick and easy. Setting up parking and airport shuttle was easy. I will definitely use this hotel and services again!

Reviewed on Dec 24, 2025

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Save 100% on your flight
Price was $651, price is now $466 per person
$466
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
9.6/10 Exceptional! (1,159 reviews)
The staff was friendly and some remembered me from previous stays. They also upgraded my room so that was above and beyond. Clean room and facilities as usual.

Reviewed on Dec 22, 2025

Country Inn & Suites by Radisson, Billings, MT

Country Inn & Suites by Radisson, Billings, MT

3 out of 5
Price was $523, price is now $401 per person
$401
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
8.2/10 Very Good! (1,000 reviews)
Staff said nothing 😍no greeting

Reviewed on Dec 15, 2025

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
Downtown Billings
Price was $550, price is now $444 per person
$444
per person
Jan 29 - Feb 2
found 7 hours ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
8.2/10 Very Good! (1,002 reviews)
Very kind and helpful young man at the front desk. Thank you so much!

Reviewed on Dec 23, 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
$66 nightly
The price is $76 total per night from Dec 28 to Dec 29
$76 total
Dec 28 - Dec 29
Total with taxes and fees
7.8/10 Good! (1,160 reviews)
Clean room, comfortable bed. Great place to stop when passing through.

Reviewed on Dec 20, 2025

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
$59 nightly
The price is $67 total per night from Dec 29 to Dec 30
$67 total
Dec 29 - Dec 30
Total with taxes and fees
6/10 (1,006 reviews)
Fast checkin

Reviewed on Dec 18, 2025

Howard Johnson by Wyndham Billings
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
$110 nightly
The price is $122 total per night from Jan 4 to Jan 5
$122 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.6/10 Exceptional! (326 reviews)
Very nice new hotel on the West End. Staff is kind. You can get a glass of wine or a beer and they have a small food menu. We’ve stayed here a couple times and enjoy it.

Reviewed on Dec 19, 2025

Hyatt Place Billings
See all 273 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 $330 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.