Shepherd Vacations from $670

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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.
Montana Trailhead Inn

Montana Trailhead Inn

2.5 out of 5
Price was $764, price is now $670 per person
$670
per person
Jun 18 - Jun 23
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Billings (BIL)
8/10 Very Good! (1,326 reviews)
Room was 75° when we arrived. Ac did nothing. Slept with the window open. In the morning closed the window and the room shot up to 74° again. Breakfast was very lacking. Eggs were gone, sausage was almost gone. Other guests said the coffee was gone as well. No one in the breakfast area. Room was very dated. Bathroom fan didn't work. Will not stay again

Reviewed on Mar 23, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
Price was $1,338, price is now $696 per person
$696
per person
Jun 18 - Jun 23
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Billings (BIL)
8.2/10 Very Good! (1,472 reviews)
Clean basic room. Good secure extended parking and shuttle to and from airport. Perfect for what I needed!

Reviewed on Mar 27, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,056, price is now $793 per person
$793
per person
Jun 18 - Jun 23
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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 $831, price is now $705 per person
$705
per person
Jun 18 - Jun 23
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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

Riversage Billings Inn

Riversage Billings Inn

3 out of 5
Downtown Billings
Price was $880, price is now $780 per person
$780
per person
Jun 18 - Jun 23
found 15 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Billings (BIL)
9.2/10 Wonderful! (1,014 reviews)
Breakfast was fresh and heater worked great

Reviewed on Mar 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! (1,855 reviews)
Who is a nice room nothing special nothing out of place

Reviewed on Mar 27, 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! (1,476 reviews)
Clean basic room. Good secure extended parking and shuttle to and from airport. Perfect for what I needed!

Reviewed on Mar 27, 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
$116 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
Total with taxes and fees
9.6/10 Exceptional! (409 reviews)
Very clean welcoming hotel, bright, friendly staff, modern, comfortable beds. Everything is easily accessible. 10/10 will stay again & recommend.

Reviewed on Mar 26, 2026

Hyatt Place Billings
See all 280 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 $670 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.