Shepherd Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Shepherd

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Fully refundable
The price is S$162 per night from 23 Aug to 24 Aug
S$162
23 Aug - 24 Aug
includes taxes & fees
8.8/10 Excellent! (1,943 reviews)
"Room was clean. King beds were very roomy. Breakfast was ok."

Reviewed on 23 Jul, 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
The price is S$177 per night from 5 Aug to 6 Aug
S$177
5 Aug - 6 Aug
includes taxes & fees
8.2/10 Very good! (1,681 reviews)
"This property is older, but offers many amenities. The airport shuttle is a highlight as many other properties in this area don’t offer shuttle service. Our room was easy to find, clean, quiet and spacious. The coffee shop was conveniently located in the restaurant. The fitness center was basic, ..."

Reviewed on 23 Jul, 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
The price is S$151 per night from 25 Jul to 26 Jul
S$151
25 Jul - 26 Jul
includes taxes & fees
Dude Rancher Lodge
See all 270 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.

Frequently asked questions

How much does a Shepherd holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday 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 holiday 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?
With a well-planned itinerary, you can easily hit the main Shepherd attractions in a few days. But if you'd like to discover hidden spots or go on day tours, consider booking your Shepherd holiday for longer.
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 holiday package well in advance.
Is it cheaper to book a Shepherd holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can customise 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 holiday package to Shepherd?
If you've got your Shepherd holiday 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.
How to plan a trip to Shepherd?

  1. Choose your dates: What you plan to do in Shepherd and your favourite season can help you decide when to travel.
  2. Set a budget: Consider costs like transportation, flights and meals when working out how much to save for your trip to Shepherd. Then, choose a property that matches your budget, whether that's a wallet-friendly stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the sights and activities you want 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 personalised Shepherd holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.