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 $1,711, price is now CA $1,094 per person
CA $1,094
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8.2/10 Very Good! (1,472 reviews)
Sockets where falling out of wall and lamp on side table.
Reviewed on Mar 29, 2026
Northern Hotel
Downtown Billings
Price was CA $1,734, price is now CA $1,389 per person
CA $1,389
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.6/10 Exceptional! (1,197 reviews)
I can’t think of anything else. It was very comfortble
Reviewed on Mar 15, 2026
Ledgestone Suites Hotel Billings
Price was CA $1,332, price is now CA $1,192 per person
CA $1,192
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.4/10 Exceptional! (1,435 reviews)
We loved our stay! Clean, quiet room. Starbucks right next door. Stocked kitchenette was a nice feature. We’ll come again!
Reviewed on Mar 23, 2026
Kelly Inn Billings Montana
Price was CA $1,293, price is now CA $1,205 per person
CA $1,205
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
8.6/10 Excellent! (1,877 reviews)
Breakfast was good, but steam trays were empty or nearly empty and the server was slow to fill and not really friendly. Trays were filled after a while, however, and we were able to fill our plates with alternate options in the meantime.
Reviewed on Mar 30, 2026
Riversage Billings Inn
Downtown Billings
Price was CA $1,315, price is now CA $1,227 per person
CA $1,227
per person
May 18 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
9.2/10 Wonderful! (1,014 reviews)
Breakfast was fresh and heater worked great
Reviewed on Mar 26, 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 $124 per night from Apr 14 to Apr 15
CA $124
CA $139 total
Apr 14 - Apr 15
includes taxes & fees
8.8/10 Excellent! (1,853 reviews)
No fresh fruit, no waffles, 2 machines out of order. Coffee meh. Toilets are low
Reviewed on Mar 30, 2026
Billings Hotel and Convention Center
1223 Mullowney Ln Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Apr 12 to Apr 13
CA $165
CA $191 total
Apr 12 - Apr 13
includes taxes & fees
8.2/10 Very Good! (1,482 reviews)
No contennial breakfast afte needing a 100$ inncidental that I couldn't pre pay for and had been blind sided by when in a tight spot. Do not recommend if in need for an emergency. Oh and the room service tried to enter without a notice. Good thing I had the door latch on.
Reviewed on Mar 30, 2026
Hyatt Place Billings
705 Henry Chapple Street Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Apr 19 to Apr 20
CA $175
CA $195 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (415 reviews)
All the staff were excellent and extremely helpful. They were always friendly in wanting to make our stay exceptional and memorable. We plan to stay there again during our next trip to Billings.
Reviewed on Mar 31, 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.
