Shepherd Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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$161 per night from 1 Sept to 2 Sept
S$161
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,715 reviews)
"Very clean, comfortable and friendly. Pool has a slide! Great breakfast."

Reviewed on 20 Aug, 2025

Kelly Inn Billings Montana
Woodspring Suites Billings

Woodspring Suites Billings

2.5 out of 5
4750 King Ave East, Billings, MT
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 26 Aug to 27 Aug
S$129
26 Aug - 27 Aug
includes taxes & fees
7.8/10 Good! (276 reviews)
"Check-in was smooth and quick. Person that helped us was very friendly and efficient. Some of the common areas needed cleaned. For example, the elevator had a big dust ball or something that I thought was a mouse at first! Room was nice and clean though. Obviously updated fairly recently. Bed was ..."

Reviewed on 18 Aug, 2025

Woodspring Suites Billings
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
8/10 Very Good! (1,258 reviews)
"Great clean rooms good food in the restaurant nice bartenders in the bar swimming pool is amazing kids love it"

Reviewed on 17 Aug, 2025

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Billings Hotel and Convention Center
See all 246 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.