Shepherd Vacations from $736

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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.
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $1,140, price is now $736 per person
$736
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Billings (BIL)
8.2/10 Very Good! (1,558 reviews)
Clean room, Tv/Internet service is not great because it is a brick building that was built in the 1970’s so service cuts in and out.

Reviewed on May 17, 2026

Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,034, price is now $858 per person
$858
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Billings (BIL)
9.6/10 Exceptional! (1,222 reviews)
The staff were really friendly and helpful. They went out of their way to accommodate guests. The view from the top floor was fabulous. You could see all of the trees in Billings with buildings poking through. Clouds made great designs as they floated over the city. Overall very tranquil.

Reviewed on May 17, 2026

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $1,350, price is now $1,122 per person
$1,122
per person
Jul 14 - Jul 19
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
9.8/10 Exceptional! (81 reviews)
The room was very clean. The staff exceptionally nice and kind.

Reviewed on May 19, 2026

Beartooth Hideaway Inn and Cabins

Beartooth Hideaway Inn and Cabins

2.5 out of 5
Price was $926, price is now $795 per person
$795
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9/10 Wonderful! (1,022 reviews)
This was a beautiful place. With a pool and hot tub. The room is clean and nice and the staff is so welcoming.

Reviewed on May 14, 2026

Hotel Expedition

Hotel Expedition

3.5 out of 5
Price was $1,061, price is now $911 per person
$911
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Billings (BIL)
9.2/10 Wonderful! (445 reviews)
The property was very nice. Room was nice. But there was no sink in the bathroom and the room was advertised as having a tub in the bathroom which it did not. Otherwise the room was very nice

Reviewed on May 11, 2026

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Shepherd Hotel Deals

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
$144 nightly
The price is $159 total per night from Jun 2 to Jun 3
$159 total
Jun 2 - Jun 3
Total with taxes and fees
8.2/10 Very Good! (1,577 reviews)
"Pool was great fun."

Reviewed on May 18, 2026

Billings Hotel and Convention Center
Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
415 N 29th St Billings MT
$96 nightly
The price is $108 total per night from May 25 to May 26
$108 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,161 reviews)
"Always great place to rest. Staff very nice and welcoming rooms are cozy clean dinner good hot food"

Reviewed on May 19, 2026

Dude Rancher Lodge
Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
$100 nightly
The price is $112 total per night from May 25 to May 26
$112 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (1,871 reviews)
"Upon checking in, I discovered that pets were allowed in all rooms and on all floors and I am allergic to most pet danders. I have found in the past that most hotels have rooms assigned specifically for pets. They do not. I canceled the check-in and forfeited my entire payment."

Reviewed on May 20, 2026

Kelly Inn Billings Montana
See all 275 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 $736 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.