Shepherd Vacations from $630

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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.
Country Inn & Suites by Radisson, Billings, MT

Country Inn & Suites by Radisson, Billings, MT

3 out of 5
Price was $691, price is now $630 per person
$630
per person
May 15 - May 18
found 2 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Billings (BIL)
8.4/10 Very Good! (1,006 reviews)
The staff is very nice. It is right off of a main road so there is significant road noise. The property could use some better maintenance. There was some paint chippage and paint splatter on the floor in the bathroom. Also could be a little cleaner, there was stains on the curtains. All together not a horrible stay, it gets the job done but definitely not the nicest stay.

Reviewed on Mar 9, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
Price was $1,447, price is now $827 per person
$827
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Billings (BIL)
8.2/10 Very Good! (1,472 reviews)
Beds are not very comfortable, pool area is a bit small. Pretty average stay experience

Reviewed on Mar 23, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,111, price is now $903 per person
$903
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Billings (BIL)
9.6/10 Exceptional! (1,197 reviews)
I can’t think of anything else. It was very comfortble

Reviewed on Mar 15, 2026

Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $884, price is now $795 per person
$795
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Billings (BIL)
9.4/10 Exceptional! (1,435 reviews)
We loved our stay! Clean, quiet room. Starbucks right next door. Stocked kitchenette was a nice feature. We’ll come again!

Reviewed on Mar 23, 2026

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $1,996, price is now $1,838 per person
$1,838
per person
Jun 11 - Jun 14
found 12 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Billings (BIL)
9.6/10 Exceptional! (66 reviews)
Very elegant, clean and beautiful. We were sorry there was no food or bar service in the off season. But the setting, pool, saunas and hikes made up for that. Plan your food ahead or book when they are serving.

Reviewed on Feb 26, 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
$86 nightly
The price is $97 total per night from Apr 12 to Apr 13
$97 total
Apr 12 - Apr 13
Total with taxes and fees
8.8/10 Excellent! (1,851 reviews)
Breakfast was just ok. Pool with slide is a great hit with the kids. Hot tub was very nice

Reviewed on Mar 23, 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 1 to Apr 2
$163 total
Apr 1 - Apr 2
Total with taxes and fees
8.2/10 Very Good! (1,474 reviews)
Beds are not very comfortable, pool area is a bit small. Pretty average stay experience

Reviewed on Mar 23, 2026

Billings Hotel and Convention Center
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Apr 5 to Apr 6
$124 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (407 reviews)
Lovely. Perfecto. Beautiful.

Reviewed on Mar 23, 2026

Hyatt Place Billings
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

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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 $630 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.