Shepherd Vacations from $453

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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

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
Price was $824, price is now $453 per person
$453
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
8.2/10 Very Good! (1,483 reviews)
Casino covered drinks

Reviewed on Apr 9, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $805, price is now $586 per person
$586
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Billings (BIL)
9.6/10 Exceptional! (1,197 reviews)
Valet is very much appreciated! Rooms are clean, quiet! Staff very nice and helpful. Would be nice to have clearer information on room rates. Would stay again.

Reviewed on Apr 8, 2026

Big Horn Resort, an Ascend Collection Hotel

Big Horn Resort, an Ascend Collection Hotel

2.5 out of 5
Price was $673, price is now $570 per person
$570
per person
May 21 - May 25
found 13 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Billings (BIL)
7.4/10 Good! (1,002 reviews)
There was plenty do for the kids to keep them entertain them without devices.

Reviewed on Apr 5, 2026

Country Inn & Suites by Radisson, Billings, MT

Country Inn & Suites by Radisson, Billings, MT

3 out of 5
Price was $865, price is now $743 per person
$743
per person
Jun 21 - Jun 26
found 15 hours ago
Roundtrip flight included
Salt Lake City (SLC) to Billings (BIL)
8.4/10 Very Good! (1,002 reviews)
Nice rooms Nice people, Beds are soft, pillows were soft. Everything was nice and clean. But, request a room on the back side of the hotel. The road noise is loud on the front. We will be staying here again. Super convenient to the airport!

Reviewed on Apr 9, 2026

Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $610, price is now $528 per person
$528
per person
May 21 - May 25
found 13 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Billings (BIL)
9.4/10 Exceptional! (1,440 reviews)
Great place. Very clean

Reviewed on Apr 8, 2026

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Shepherd Hotel Deals

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
$92 nightly
The price is $103 total per night from Apr 12 to Apr 13
$103 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (1,847 reviews)
Very welcoming front desk staff. I asked about parking our car which was towing a trailer and he pointed us in the right direction. No issues at all. The room was clean and comfortable.

Reviewed on Apr 7, 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 Apr 12 to Apr 13
$163 total
Apr 12 - Apr 13
Total with taxes and fees
8.2/10 Very Good! (1,499 reviews)
Casino covered drinks

Reviewed on Apr 9, 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
$86 nightly
The price is $97 total per night from Apr 11 to Apr 12
$97 total
Apr 11 - Apr 12
Total with taxes and fees
8.6/10 Excellent! (1,126 reviews)
Disappointing. Room very very small. Expensive. Advertisement overrated what you were getting. Will not consider next time when traveling to Billings

Reviewed on Apr 5, 2026

Dude Rancher Lodge
See all 286 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

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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 $453 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.