Shepherd Vacations from $576

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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.
Days Inn by Wyndham Billings

Days Inn by Wyndham Billings

2 out of 5
Southwest Corridor
Price was $659, price is now $576 per person
$576
per person
Sep 9 - Sep 13
found 24 hours ago
Roundtrip flight included
Minneapolis (MSP) to Billings (BIL)
8.2/10 Very Good! (1,312 reviews)
Easy check in & check out. Room was clean. Breakfast was satisfactory.

Reviewed on Jun 24, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $834, price is now $584 per person
$584
per person
Jul 24 - Jul 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
8.2/10 Very Good! (1,626 reviews)
The pool and slides are unmatched when compared to other hotels. For kids it's like a hotel and water park in one. It was a hit with our kids, ages 7, 9, 11.

Reviewed on Jun 24, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $924, price is now $779 per person
$779
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Billings (BIL)
9.6/10 Exceptional! (1,244 reviews)
Clean, quiet, updated and convenient. We really enjoyed our stay at the Northern hotel.

Reviewed on Jun 14, 2026

Best Western Plus Kelly Inn & Suites

Best Western Plus Kelly Inn & Suites

2.5 out of 5
Southwest Corridor
Price was $878, price is now $793 per person
$793
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Billings (BIL)
9.2/10 Wonderful! (1,006 reviews)
Room was spacious and very clean. No carpet!!! Great pool/hot tub. Friendly staff. Highly recommended.

Reviewed on Jun 24, 2026

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
Southwest Corridor
Price was $791, price is now $722 per person
$722
per person
Aug 27 - Aug 30
found 20 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Billings (BIL)
8.8/10 Excellent! (1,911 reviews)
Room was clean and nice, bathroom could have been a little more cleaner, but still ok.

Reviewed on Jun 22, 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
$112 nightly
The price is $125 total per night from Jul 13 to Jul 14
$125 total
Jul 13 - Jul 14
Total with taxes and fees
8.8/10 Excellent! (1,889 reviews)
"Had the two king bed room...really appreciated this feature. The beds weren't comfortable for my spouse and I but my kids thought they were great. I think beds are a very personalized choice (therefore no points deducted for this) and I needed something a little softer but I will say it wasn't rock ..."

Reviewed on Jun 24, 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
$124 nightly
The price is $137 total per night from Jul 1 to Jul 2
$137 total
Jul 1 - Jul 2
Total with taxes and fees
8.2/10 Very Good! (1,623 reviews)
"The pool and slides are unmatched when compared to other hotels. For kids it's like a hotel and water park in one. It was a hit with our kids, ages 7, 9, 11."

Reviewed on Jun 24, 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
$106 nightly
The price is $119 total per night from Jun 28 to Jun 29
$119 total
Jun 28 - Jun 29
Total with taxes and fees
8.6/10 Excellent! (1,213 reviews)
"Wonderful, friendly staff, clean room, perfect for the night before flight!"

Reviewed on Jun 24, 2026

Dude Rancher Lodge
See all 274 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 $576 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.