
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.

Western Executive Inn
West End
Price was CA $1,660, price is now CA $1,429 per person
CA $1,429
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Billings (BIL)
8.2/10 Very Good! (228 reviews)
The front desk man was welcoming. I had called directly to ask about adding a pet as Expedia website didn’t give me the option. He said no worries he would add it when we arrived. Excellent price compared to other hotels. Not fancy and no elevator but the room was clean, quiet, comfortable bed, sheets and towels were clean and very adequate. The carpeting was worn. More importantly everything worked well in room, shower was great. Little freezer space kept our gel pack frozen and refrigerator was cold.
Nice location to walk our dog. Lots of restaurants close by.
Reviewed on May 18, 2026

Billings Hotel and Convention Center
Southwest Corridor
Price was CA $2,381, price is now CA $1,489 per person
CA $1,489
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Billings (BIL)
8.2/10 Very Good! (1,558 reviews)
Clean room, Tv/Internet service is not great because it is a brick building that was built in the 1970’s so service cuts in and out.
Reviewed on May 17, 2026

Northern Hotel
Downtown Billings
Price was CA $2,159, price is now CA $1,750 per person
CA $1,750
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Billings (BIL)
9.6/10 Exceptional! (1,222 reviews)
The staff were really friendly and helpful. They went out of their way to accommodate guests.
The view from the top floor was fabulous. You could see all of the trees in Billings with buildings poking through. Clouds made great designs as they floated over the city. Overall very tranquil.
Reviewed on May 17, 2026

avid Hotels Billings West by IHG
Shiloh
Price was CA $1,798, price is now CA $1,595 per person
CA $1,595
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Billings (BIL)
9.4/10 Exceptional! (366 reviews)
The breakfast prep lady had breakfast set up early! The biscuits were fantastic. The whole hotel - the room, the pool & spa, the exercise room - pristine! Bed & pillows were exceptional.
Reviewed on May 18, 2026

Ledgestone Suites Hotel Billings
Southwest Corridor
Price was CA $1,680, price is now CA $1,530 per person
CA $1,530
per person
Jun 20 - Jun 26
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Billings (BIL)
9.4/10 Exceptional! (1,482 reviews)
The Ledgestone is one of my favorite places to stay. It's affordable and close by to important areas when my daughter is in town competing. Our last trip however had some sort of broken bed situation. I'm not sure what was going on. It didn't feel sturdy. Every time we get back from competition it's usually about 11 PM and there's no one at the front desk. When I had a moment during checkout, I let the manager on duty know about the condition of the bed and that we had slept on the futon the entire weekend. She assured me we would receive some sort of credit and gave me her card and let me know to contact her if I had any questions. They were still figuring out the new computer system and she wasn't sure how to process that transaction. I contacted the email on the card as I am usually at work and don't have many moments to step away and make a phone call during business hours. I have not heard back.
Reviewed on May 16, 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 $163 per night from May 19 to May 20
CA $163
CA $189 total
May 19 - May 20
includes taxes & fees
8.2/10 Very Good! (1,574 reviews)
"Pool was great fun."
Reviewed on May 18, 2026

Dude Rancher Lodge
415 N 29th St Billings MT
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from May 19 to May 20
CA $119
CA $134 total
May 19 - May 20
includes taxes & fees
8.6/10 Excellent! (1,160 reviews)
"Dated and a bit noisy but shower was great. Staff was very friendly and helpful"
Reviewed on May 18, 2026

Kelly Inn Billings Montana
5610 South Frontage Road Billings MT
Fully refundable
The price is CA $139 per night from May 24 to May 25
CA $139
CA $156 total
May 24 - May 25
includes taxes & fees
8.8/10 Excellent! (1,867 reviews)
"Rooms were nice and a lot of space"
Reviewed on May 17, 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.







