Shepherd Vacation Packages

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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.

Top Shepherd Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ledgestone Hotel Billings

Ledgestone Hotel Billings

2.5 out of 5
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
9.4/10 Exceptional! (1,121 reviews)
We failed to notice that there's no breakfast which was our own fault, but our bed had sweaty, slippery, slimy polyester sheets, which was THEIR fault! Towels were great though!

Reviewed on Jul. 13, 2025

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Save 100% on your flight
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8/10 Very Good! (1,138 reviews)
Clean rooms. Nice people. Waterslides are fun!

Reviewed on Jul. 12, 2025

DoubleTree by Hilton Hotel Billings

DoubleTree by Hilton Hotel Billings

4 out of 5
North Park
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8.2/10 Very Good! (1,001 reviews)
Central location plenty of bars and restaurants.

Reviewed on Jun. 28, 2025

SureStay Plus Hotel by Best Western Billings

SureStay Plus Hotel by Best Western Billings

2.5 out of 5
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
8.8/10 Excellent! (1,003 reviews)
Floor plan not laid out well

Reviewed on Jul. 13, 2025

Courtyard BY Marriott Billings

3 out of 5
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Billings (BIL)
10/10 Exceptional! (9 reviews)
Very clean, modern rooms.

Reviewed on Apr. 26, 2025

Ready to book your vacation to Shepherd?

 

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Shepherd Hotel Deals

Super 8 by Wyndham Billings
Super 8 by Wyndham Billings
2 out of 5
5400 Southgate Dr, Billings, MT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 3 to Aug 4
CA $122
CA $137 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,428 reviews)
"Good location and quiet! We will stay here every time!"

Reviewed on Jul. 10, 2025

Super 8 by Wyndham Billings
Quality Inn
Quality Inn
2.5 out of 5
2036 Overland Ave, Billings, MT
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 3 to Aug 4
CA $131
CA $147 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"He was clean, fairly easy to get to the room. Staff was fantastic. No ice bucket in the room"

Reviewed on Jul. 9, 2025

Quality Inn
Kelly Inn Billings Montana
Kelly Inn Billings Montana
2.5 out of 5
5610 South Frontage Road, Billings, MT
Fully refundable
The price is CA $152 per night from Jul 27 to Jul 28
CA $152
CA $170 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,648 reviews)
"Great breakfast"

Reviewed on Jul. 11, 2025

Kelly Inn Billings Montana
See all 262 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Shepherd vacation package cost?
Offering excellent value package deals from CA $796 on Expedia, you'll be pleasantly surprised at how much a vacation to Shepherd costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Shepherd?
To score cheap Shepherd vacation packages, plan your getaway outside of peak periods such as school holidays. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Shepherd?
Typically, a handful of days is enough to go to the major sights during your Shepherd vacation. But if you'd like to have time to relax or take day tours, think about extending your trip.
How to find the best Shepherd package deals?
Start your search for a Shepherd package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Shepherd package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Shepherd escape underway.
Is it cheaper to book a Shepherd vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Shepherd vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Shepherd?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Shepherd trip.
How to plan a trip to Shepherd?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Shepherd.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your hotel will likely be the biggest expense during your trip to Shepherd.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to experience in Shepherd. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Shepherd vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.