Shepherd Vacations from $557

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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.
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $591, price is now $557 per person
$557
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.4/10 Exceptional! (1,313 reviews)
A good place to stay

Reviewed on Nov 7, 2025

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $797, price is now $664 per person
$664
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.6/10 Exceptional! (1,120 reviews)
Stayed their several times and.its always a great stay.

Reviewed on Nov 5, 2025

Candlewood Suites Billings West by IHG

Candlewood Suites Billings West by IHG

2.5 out of 5
Price was $882, price is now $827 per person
$827
per person
Dec 30 - Jan 4
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.8/10 Exceptional! (16 reviews)
The building is relatively new. The roof was very comfortable and have a small kitchenette, which was perfect for me. Definitely have to check out their other building when I get to Omaha or St. Louis.

Reviewed on Oct 28, 2025

avid Hotels Billings West by IHG

avid Hotels Billings West by IHG

2.5 out of 5
Price was $865, price is now $812 per person
$812
per person
Dec 30 - Jan 4
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.4/10 Exceptional! (269 reviews)
Room was spotless. Staff was courteous.

Reviewed on Nov 2, 2025

Holiday Inn Express & Suites Billings by IHG

Holiday Inn Express & Suites Billings by IHG

2.5 out of 5
Price was $855, price is now $804 per person
$804
per person
Dec 30 - Jan 4
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.2/10 Wonderful! (513 reviews)
The room was clean and the staff was very pleasant!

Reviewed on Nov 8, 2025

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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
$102 nightly
The price is $114 total per night from Nov 23 to Nov 24
$114 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,783 reviews)
The room was really nice. The bed was really comfortable. Check in was quick but professional. The property itself could use some updating, but overall a nice place.

Reviewed on Nov 4, 2025

Kelly Inn Billings Montana
Woodspring Suites Billings

Woodspring Suites Billings

2.5 out of 5
4750 King Ave East, Billings, MT
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $73 total per night from Dec 7 to Dec 8
$73 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (402 reviews)
The room was awesome. Very nice and clean

Reviewed on Nov 5, 2025

Woodspring Suites Billings
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street, Billings, MT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $131 total per night from Dec 4 to Dec 5
$131 total
Dec 4 - Dec 5
Total with taxes and fees
9.6/10 Exceptional! (290 reviews)
Wonderfully clean and the pool and hot tub area is fantastic!

Reviewed on Nov 4, 2025

Hyatt Place Billings
See all 256 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 $557 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.