Shepherd Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Billings Hotel and Convention Center
Price was CA $2,466, price is now CA $1,130 per person
CA $1,130
per person
Jun 13 - Jun 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
8.2/10 Very Good! (1,506 reviews)
Didn’t eat breakfast but the parking was good
Reviewed on Apr 24, 2026
Northern Hotel
Downtown Billings
Price was CA $1,995, price is now CA $1,439 per person
CA $1,439
per person
Jun 13 - Jun 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
9.6/10 Exceptional! (1,206 reviews)
Very nice room although street noise was a little loud but no big deal. Easy, friendly check-in and then had dinner at TEN. Honestly, one of the best martinis and delicious carne asada tacos.
Reviewed on Apr 26, 2026
Home2 Suites by Hilton Billings
Downtown Billings
Price was CA $1,828, price is now CA $1,425 per person
CA $1,425
per person
Jun 13 - Jun 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
9.4/10 Exceptional! (624 reviews)
Did not like the yogurt machine.
Reviewed on Apr 20, 2026
Hilton Garden Inn Billings
Price was CA $1,669, price is now CA $1,346 per person
CA $1,346
per person
Jun 13 - Jun 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
9/10 Wonderful! (893 reviews)
This hotel was wonderful. Staff was incredibly friendly and welcoming, the pool and spa area was very clean and well stocked with towels. We enjoyed our stay. Will definitely book here again next time we need to be in Billings.
Reviewed on Apr 20, 2026
Country Inn & Suites by Radisson, Billings, MT
Price was CA $1,577, price is now CA $1,291 per person
CA $1,291
per person
Jun 13 - Jun 20
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Billings (BIL)
8.4/10 Very Good! (1,002 reviews)
the room was very clean and the staff was amazing. ac worked perfect too
Reviewed on Apr 23, 2026
Shepherd Hotel Deals
Billings Hotel and Convention Center
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Apr 27 to Apr 28
CA $162
CA $188 total
Apr 27 - Apr 28
includes taxes & fees
Kelly Inn Billings Montana
5610 South Frontage Road Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from May 3 to May 4
CA $140
CA $157 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,853 reviews)
I was upset when the hotel front desk was not nice to others.
Reviewed on Apr 23, 2026
Dude Rancher Lodge
415 N 29th St Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Apr 27 to Apr 28
CA $122
CA $137 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (1,135 reviews)
Absolutely the best deal in Billings. Cheap and quaint.
Reviewed on Apr 25, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
