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Shepherd Vacation Packages

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Shepherd Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Western Executive Inn

Western Executive Inn

2.5 out of 5
Price was $519, price is now $461 per person
$461
per person
Jan 7 - Jan 10
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) 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

Billings Hotel and Convention Center

3 out of 5
Price was $787, price is now $571 per person
$571
per person
Jan 7 - Jan 10
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) 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.

Northern Hotel

Northern Hotel

4 out of 5
Price was $703, price is now $600 per person
$600
per person
Nov 14 - Nov 17
found 20 hours ago
Roundtrip flight included
Dallas (DFW) 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.

Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $725, price is now $668 per person
$668
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Billings (BIL)
Stay at this lodge in Red Lodge. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Nichols Creek Trailhead and Lake Fork Trail are located nearby.

Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $937, price is now $888 per person
$888
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Billings (BIL)
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 First Interstate Arena at MetraPark and Amend Park are located nearby.

Dude Rancher Lodge

Dude Rancher Lodge

3 out of 5
Price was $794, price is now $759 per person
$759
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Billings (BIL)
Book a stay at this business-friendly motel in Billings. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions First Interstate Arena at MetraPark and Alberta Bair Theater are located nearby.
good location downtown - easy walk to restaurants it's a little dated, but charming clean, comfortable, friendly fridge & microwave helpful big discount for delicious breakfast at attached restaurant

Reviewed on Oct 15, 2026

Hilltop Inn by Riversage

Hilltop Inn by Riversage

3 out of 5
Price was $584, price is now $573 per person
$573
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip 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 helpful staff in our reviews. Popular attractions First Interstate Arena at MetraPark and Dehler Park are located nearby.
Room was clean and breakfast was better than expected-keep in mind this is right next to a hospital so sirens/ flight for life helicopter noise is possible.

Reviewed on Oct 15, 2026

My Place Hotel - Billings, MT

My Place Hotel - Billings, MT

2 out of 5
Price was $886, price is now $883 per person
$883
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.
GREAT!!

Reviewed on Oct 15, 2026

Shepherd Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Western Executive Inn

Western Executive Inn

2.5 out of 5
West End
Price was $519, price is now $461 per person
$461
per person
Jan 7 - Jan 10
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to Billings (BIL)
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $787, price is now $571 per person
$571
per person
Jan 7 - Jan 10
found 1 hour ago
Roundtrip flight included
Los Angeles (LAX) to Billings (BIL)
Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $703, price is now $600 per person
$600
per person
Nov 14 - Nov 17
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Billings (BIL)
Rock Creek Resort

Rock Creek Resort

4 out of 5
Price was $725, price is now $668 per person
$668
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Billings (BIL)

Shepherd Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Southwest Corridor
Price was $937, price is now $888 per person
$888
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Billings (BIL)
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $1,740, price is now $1,224 per person
$1,224
per person
Dec 4 - Dec 10
found 13 hours ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)
Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,769, price is now $1,619 per person
$1,619
per person
Dec 4 - Dec 10
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)
Western Executive Inn

Western Executive Inn

2.5 out of 5
West End
Price was $1,319, price is now $1,252 per person
$1,252
per person
Dec 4 - Dec 10
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Tue, Dec 15 - Wed, Jan 6
SEA
Seattle - Tacoma Intl.
BIL
Logan Intl.
$225 Roundtrip, found 1 day ago
$225
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Dec 15 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, Jan 6, priced at $225 found 1 day ago
Bargain Flight
Tue, Nov 3 - Sat, Nov 14
PDX
Portland Intl.
BIL
Logan Intl.
$265 Roundtrip, found 3 days ago
$265
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Nov 3 from Portland Intl. to Logan Intl., returning Sat, Nov 14, priced at $265 found 3 days ago
Bargain Flight
Sat, Nov 21 - Sat, Dec 5
LAS
Harry Reid Intl.
BIL
Logan Intl.
$284 Roundtrip, found 4 days ago
$284
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Sat, Nov 21 from Harry Reid Intl. to Logan Intl., returning Sat, Dec 5, priced at $284 found 4 days ago
Bargain Flight
Tue, Nov 3 - Wed, Nov 4
PHX
Sky Harbor Intl.
BIL
Logan Intl.
$295 Roundtrip, found 3 days ago
$295
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Nov 3 from Sky Harbor Intl. to Logan Intl., returning Wed, Nov 4, priced at $295 found 3 days ago