Search Deals onShepherd Vacation Packages
Shepherd Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Western Executive Inn
Price was $787, price is now $692 per person
$692
per person
Dec 12 - Dec 18
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
Stay at this hotel in Billings. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Magic Diamond Casino and Onyx Casino are located nearby.
Billings Hotel and Convention Center
Price was $1,308, price is now $856 per person
$856
per person
Dec 12 - Dec 18
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 First Interstate Arena at MetraPark and Copper Creek Casino are located nearby.
Beautiful hotel. Great food and nice casino.
Reviewed on Oct 9, 2026
Northern Hotel
Price was $1,261, price is now $975 per person
$975
per person
Dec 12 - Dec 18
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Billings (BIL)
Book a stay at this luxury hotel in Billings. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the bar in our reviews. Popular attractions First Interstate Arena at MetraPark and Western Heritage Center are located nearby.
Locomotive Inn
Price was $1,105, price is now $1,021 per person
$1,021
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Billings (BIL)
Stay at this motel in Laurel. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Black Chip Casino and Montana Lil's Casino are located nearby.
avid Hotels Billings West by IHG
Price was $1,102, price is now $1,034 per person
$1,034
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Billings (BIL)
Book a stay at this business-friendly hotel in Billings. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Reef Indoor Water Park and ZooMontana are located nearby.
Clean. Great breakfast
Reviewed on Oct 8, 2026
Montana Trailhead Inn
Price was $1,122, price is now $1,061 per person
$1,061
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Billings (BIL)
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 First Interstate Arena at MetraPark and Copper Creek Casino are located nearby.
My Place Hotel - Billings, MT
Price was $1,106, price is now $1,048 per person
$1,048
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Billings (BIL)
Book a stay at this business-friendly hotel in Billings. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions First Interstate Arena at MetraPark and Amend Park are located nearby.
Kelly Inn Billings Montana
Price was $1,135, price is now $1,078 per person
$1,078
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Billings (BIL)
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 First Interstate Arena at MetraPark and Copper Creek Casino are located nearby.
Shepherd Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Shepherd Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Dec 15 - Wed, Jan 6
SEA
Seattle - Tacoma Intl.
BIL
Logan Intl.
$225 Roundtrip, found 1 hour ago
$225
Roundtrip
found 1 hour ago
Tue, Nov 3 - Sat, Nov 14
PDX
Portland Intl.
BIL
Logan Intl.
$251 Roundtrip, found 4 days ago
$251
Roundtrip
found 4 days ago
Sat, Nov 21 - Sat, Dec 5
LAS
Harry Reid Intl.
BIL
Logan Intl.
$284 Roundtrip, just found
$284
Roundtrip
just found
Fri, Oct 30 - Wed, Nov 4
BNA
Nashville Intl.
BIL
Logan Intl.
$290 Roundtrip, found 2 days ago
$290
Roundtrip
found 2 days ago
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