Shepherd Vacations from $652

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.
Western Executive Inn

Western Executive Inn

3 out of 5
West End
Price was $767, price is now $652 per person
$652
per person
Jun 25 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Billings (BIL)
8.2/10 Very Good! (228 reviews)
Like da young lady on front very helpful and made me feel at home.

Reviewed on May 7, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $1,042, price is now $711 per person
$711
per person
Jun 25 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Billings (BIL)
8.2/10 Very Good! (1,539 reviews)
Clean and friendly staff. Price is reasonable as well. The food at their lounge is great.

Reviewed on May 7, 2026

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $1,992, price is now $1,678 per person
$1,678
per person
Jun 18 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Richmond (RIC) to Billings (BIL)
9.6/10 Exceptional! (80 reviews)
Had an amazing stay! Staff was super friendly and helpful and the rooms were amazing!

Reviewed on Apr 29, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $893, price is now $753 per person
$753
per person
Jun 25 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Billings (BIL)
9.6/10 Exceptional! (1,211 reviews)
No refrigerator, microwave or coffee maker in room which is inconvenient for an extended stay. Restaurant on site for drinkable coffee but free lobby coffee was not worth drinking. Overall a good location and quiet room.

Reviewed on May 4, 2026

My Place Hotel - Billings, MT

My Place Hotel - Billings, MT

2 out of 5
Southwest Corridor
Price was $756, price is now $652 per person
$652
per person
Jun 25 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Billings (BIL)
8.6/10 Excellent! (901 reviews)
Great facility clean room

Reviewed on May 9, 2026

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

Shepherd Hotel Deals

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
$96 nightly
The price is $108 total per night from May 25 to May 26
$108 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,870 reviews)
Clean room. It was peaceful and quiet. The bed in my room was super comfortable. I'll visit again for sure.

Reviewed on May 9, 2026

Kelly Inn Billings Montana
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $163 total per night from May 11 to May 12
$163 total
May 11 - May 12
Total with taxes and fees
8.2/10 Very Good! (1,553 reviews)
I have mixed feelings. The beds were comfortable, however the floors hadn’t been vacuumed. There was a lot of dried rice, and coffee straws all over the floor. The coffee straws blended in with the carpet but could have been found with a vacuum. Major cracks in the ceiling. Buggers on the walls next ...

Reviewed on May 10, 2026

Billings Hotel and Convention Center
Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
415 N 29th St Billings MT
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $108 total per night from May 12 to May 13
$108 total
May 12 - May 13
Total with taxes and fees
8.6/10 Excellent! (1,151 reviews)
I like the rustic atmosphere and the staff is always kind and helpful.

Reviewed on May 9, 2026

Dude Rancher Lodge
See all 277 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 $652 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.