Book Exclusive Shepherd Vacation Packages

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Shepherd flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Price was CA $1,638, price is now CA $970 per person
CA $970
per person
Feb 13 - Feb 18
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
Stay at this hotel in Billings. Enjoy free WiFi, free parking, and a casino. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Copper Creek Casino and Lucky Lil's Casino are located nearby.
Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was CA $1,464, price is now CA $1,138 per person
CA $1,138
per person
Feb 13 - Feb 18
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
Book a stay at this business-friendly hotel in Billings. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions Skypoint and Western Heritage Center are located nearby.
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
Price was CA $1,142, price is now CA $1,142 per person
CA $1,142
per person
Feb 13 - Feb 18
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Billings (BIL)
Stay at this hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Casino Mardi Gras West and Dotty's Casino are located nearby.

Top Shepherd hotels deals

Days Inn by Wyndham Billings

Days Inn by Wyndham Billings

2 out of 5
843 Parkway Ln Billings MT
Free cancellation
Reserve now, pay when you stay
The price is CA $90 per night
CA $90
CA $103 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this business-friendly hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Copper Creek Casino and Amend Park are located nearby.
Breakfast included
Pet-friendly
Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
5610 South Frontage Road Billings MT
Free cancellation
The price is CA $116 per night
CA $116
CA $131 total
Dec 14 - Dec 15
includes taxes & fees
Stay at this hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Copper Creek Casino and Lucky Lil's Casino are located nearby.
Pool
Hot tub
Hyatt Place Billings

Hyatt Place Billings

3 out of 5
705 Henry Chapple Street Billings MT
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
CA $169 total
Dec 25 - Dec 26
includes taxes & fees
Stay at this hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Casino Mardi Gras West and Dotty's Casino are located nearby.
Pool
Breakfast included
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
4863 King Ave E Billings MT
Free cancellation
Reserve now, pay when you stay
The price is CA $121 per night
CA $121
CA $137 total
Jan 12 - Jan 13, 2026
includes taxes & fees
Book a stay at this business-friendly hotel in Billings. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Amend Park and Riverfront Park are located nearby.
Pet-friendly
Parking included
Hilltop Inn by Riversage

Hilltop Inn by Riversage

3 out of 5
1116 North 28th St. Billings MT
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dehler Park and Pioneer Park are located nearby.
Breakfast included
Pet-friendly
Montana Trailhead Inn

Montana Trailhead Inn

2.5 out of 5
5500 Midland Rd Billings MT
Free cancellation
Reserve now, pay when you stay
Get rates
Book a stay at this business-friendly hotel in Billings. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Copper Creek Casino and Amend Park are located nearby.
Breakfast included
Pet-friendly
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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.

Shepherd Vacations

Are you ready for your next vacation? Make sure you don't miss out on any fun in Shepherd by learning a few facts about it before you take off.

This town is located 14 miles (23 kilometers) to the northeast of Billings, and 1,650 miles (2,655 kilometers) to the west of Washington, the national capital.

This area of Montana is home to about 500 residents.

Places to visit in Shepherd

Go take a look at the events calendar at MetraPark for a variety of lively shows. Book your ticket soon to make sure you get a great seat! Want more ideas? Eager to alleviate the stress of your busy, modern life? Enjoy the fresh air as you embark on an adventure through Lake Elmo State Park. And there's still more going on in the surrounding area. With its flashing lights and bleeping machines, Town & Country Lanes and Lounge is a lively and colorful place to visit. Have a game of pinball or just enjoy watching the kids try and choose which game to play first!

Where do you fly into for Shepherd?

Slip on your headphones and enjoy the in-flight entertainment. Before you know it, you'll be touching down at Logan International Airport (BIL). It's about 14 miles (23 kilometers) from central Shepherd.

Frequently asked questions

How much are vacation packages to Shepherd?
Travelocity provides flight and hotel vacation packages starting as low as CA $970. With these kinds of bargains, you'll be saying hello to Shepherd in a flash.
Where can I get the best vacation package deals for Shepherd?
You'll discover an excellent range of Shepherd package deals on Travelocity. With 400 partner airlines and 1,000,000 worldwide properties, piecing together the perfect getaway will be a breeze.
Why should I purchase my Shepherd vacation package via Travelocity?
By booking your flights, hotel, car rental and activities altogether, you'll save time and money. All our bookings come with a dedicated team of experts available 24/7, and you'll know that you'll always score the best deal possible with our Price Match Guarantee. So, what's stopping you? Book that dream vacation today and start packing!
Will I save money on my Shepherd car rental if I book it with hotels and flights?
Sure can. And our Shepherd vacation packages are the perfect way to do it. With just a few clicks you can save money as well as time by booking everything in one place. Pick up the keys to your rental car and do your vacation your way. Searching for things to do? Throw some tours or experiences into your package and save on those too.
Which airport is best for Shepherd?
Logan Intl. Airport (BIL) is 23 kilometers southwest of downtown Shepherd.
Where should I stay when visiting Shepherd?
Many travelers hit the hay at the See the stars from this cozy guest cabin 30 minutes from Billings.. It's sure to be a great base for your Shepherd escape.

Photos of local treasures

Browse Shepherd vacation photos for more inspiration