Shepherd Vacations from $504

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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.
Western Executive Inn

Western Executive Inn

2.5 out of 5
West End
Price was $602, price is now $504 per person
$504
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
8/10 Very Good! (324 reviews)
We thought it was closed when we pulled up - big delivery of boxes in the checkin area no one present man cleaning the floor checked us in - carpet old and dirty

Reviewed on Jul 14, 2026

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Save 100% on your flight
Price was $1,080, price is now $631 per person
$631
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
8.2/10 Very Good! (1,640 reviews)
great place

Reviewed on Jul 15, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,016, price is now $786 per person
$786
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
9.6/10 Exceptional! (1,221 reviews)

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $1,383, price is now $1,152 per person
$1,152
per person
Sep 19 - Sep 26
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
9.8/10 Exceptional! (107 reviews)
Great.

Reviewed on Jul 16, 2026

My Place Hotel - Billings, MT

My Place Hotel - Billings, MT

2 out of 5
Southwest Corridor
Price was $782, price is now $671 per person
$671
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
8.8/10 Excellent! (990 reviews)
Big room with kitchen, place was outdated but clean and spacious

Reviewed on Jul 12, 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
$118 nightly
The price is $131 total per night from Jul 19 to Jul 20
$131 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,925 reviews)
"Rooms are a good size and clean."

Reviewed on Jul 16, 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 22 to Jul 23
$137 total
Jul 22 - Jul 23
Total with taxes and fees
8.2/10 Very Good! (1,662 reviews)
"great place"

Reviewed on Jul 15, 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
$112 nightly
The price is $125 total per night from Jul 19 to Jul 20
$125 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (1,267 reviews)
"Honestly a great place in downtown Billings. Quiet, safe and affordable. Do wish the bathrooms were updated as the toilets are small and low. But will stay again."

Reviewed on Jul 15, 2026

Dude Rancher Lodge
See all 276 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 $504 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.