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.
Billings Hotel and Convention Center
Price was CA $1,670, price is now CA $876 per person
CA $876
per person
Mar 17 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8/10 Very Good! (1,349 reviews)
Very friendly staff. We will definitely stay there again!
Reviewed on Jan 27, 2026
Northern Hotel
Downtown Billings
Price was CA $1,434, price is now CA $1,079 per person
CA $1,079
per person
Mar 17 - Mar 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.6/10 Exceptional! (1,147 reviews)
I love The Northern! Great location, service, and food. My favorite place to stay in Billings 🌟
Reviewed on Feb 4, 2026
Shepherd Hotel Deals
Kelly Inn Billings Montana
5610 South Frontage Road Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Feb 8 to Feb 9
CA $121
CA $137 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (1,856 reviews)
Friendly staff and a clean room. Really enjoyed having an exterior door to the room.
Reviewed on Feb 2, 2026
Hyatt Place Billings
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Feb 15 to Feb 16
CA $143
CA $160 total
Feb 15 - Feb 16
includes taxes & fees
9.4/10 Exceptional! (374 reviews)
The hotel and room were clean and comfortable. We enjoyed the pool and the breakfast was delicious. The only drawback was the extremely loud road noise which woke us up all night.
Reviewed on Feb 2, 2026
Billings Hotel and Convention Center
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
8/10 Very Good! (1,433 reviews)
Good place to be
Reviewed on Feb 2, 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.
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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.
