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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.
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Price was $581, price is now $550 per person
$550
per person
Jan 7 - Jan 10
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 Amend Park and Riverfront Park are located nearby.

Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Price was $1,670, price is now $1,139 per person
$1,139
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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
Price was $1,460, price is now $1,316 per person
$1,316
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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 Western Heritage Center and Skypoint are located nearby.

Western Executive Inn

Western Executive Inn

2.5 out of 5
Price was $699, price is now $632 per person
$632
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip non-stop 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.

Super 8 by Wyndham Billings

Super 8 by Wyndham Billings

2 out of 5
Price was $1,033, price is now $950 per person
$950
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)
Book a stay at this business-friendly motel in Billings. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Amend Park and Copper Creek Casino are located nearby.
The breakfast was all that you need for a good nourishing meal to start your day. Very hygienic I must say. They also had a coin washer and dryer which I think was ideal for my stay. I will recommend this hotel to anyone. I wish they had a branch in Miami because I will always need a place like this in Miami. Reasonable price and very comfortable.

Reviewed on Oct 29, 2026

Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
Price was $615, price is now $570 per person
$570
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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 Copper Creek Casino and Lucky Lil's Casino are located nearby.

Baymont by Wyndham Billings

Baymont by Wyndham Billings

2.5 out of 5
Price was $990, price is now $930 per person
$930
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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 Lucky Lil's Casino and Copper Creek Casino are located nearby.
One beds had spots on the sheets, but was otherwise excellent

Reviewed on Oct 28, 2026

Montana Trailhead Inn

Montana Trailhead Inn

2.5 out of 5
Price was $1,091, price is now $1,048 per person
$1,048
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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 Copper Creek Casino and Amend Park are located nearby.

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 $578, price is now $532 per person
$532
per person
Dec 11 - Dec 15
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Billings (BIL)
Billings Hotel and Convention Center

Billings Hotel and Convention Center

3 out of 5
Southwest Corridor
Price was $947, price is now $629 per person
$629
per person
Dec 11 - Dec 15
found 7 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Billings (BIL)
Kelly Inn Billings Montana

Kelly Inn Billings Montana

2.5 out of 5
Southwest Corridor
Price was $615, price is now $570 per person
$570
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Billings (BIL)
Ledgestone Suites Hotel Billings

Ledgestone Suites Hotel Billings

2.5 out of 5
Southwest Corridor
Price was $581, price is now $550 per person
$550
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Billings (BIL)

Shepherd Vacation Packages 5-7 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 $699, price is now $632 per person
$632
per person
Dec 14 - Dec 20
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 $1,670, price is now $1,139 per person
$1,139
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)
Northern Hotel

Northern Hotel

4 out of 5
Downtown Billings
Price was $1,460, price is now $1,316 per person
$1,316
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Billings (BIL)
Super 8 by Wyndham Billings

Super 8 by Wyndham Billings

2 out of 5
Southwest Corridor
Price was $1,033, price is now $950 per person
$950
per person
Dec 4 - Dec 10
found 1 day 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.

Allegiant Air
Fri, Nov 20 - Tue, Dec 8
LAS
Harry Reid Intl.
BIL
Logan Intl.
$95 Roundtrip, found 4 hours ago
$95
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Fri, Nov 20 from Harry Reid Intl. to Logan Intl., returning Tue, Dec 8, priced at $95 found 4 hours ago
Bargain Flight
Wed, Jan 20 - Tue, Feb 2
SEA
Seattle - Tacoma Intl.
BIL
Logan Intl.
$225 Roundtrip, found 8 hours ago
$225
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Wed, Jan 20 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Feb 2, priced at $225 found 8 hours ago
Alaska Airlines
Thu, Dec 17 - Thu, Dec 24
PDX
Portland Intl.
BIL
Logan Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Thu, Dec 17 from Portland Intl. to Logan Intl., returning Thu, Dec 24, priced at $257 found 2 days ago
Bargain Flight
Wed, Nov 25 - Sat, Dec 5
DFW
Dallas-Fort Worth Intl.
BIL
Logan Intl.
$301 Roundtrip, found 4 hours ago
$301
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Wed, Nov 25 from Dallas-Fort Worth Intl. to Logan Intl., returning Sat, Dec 5, priced at $301 found 4 hours ago