Search Deals onRoundup Vacation Packages
Roundup Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Riversage Billings Inn
Price was $535, price is now $500 per person
$500
per person
Oct 23 - Oct 25
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.
Billings Hotel and Convention Center
Price was $1,254, price is now $818 per person
$818
per person
Oct 15 - Oct 19
found 1 day 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.
Northern Hotel
Price was $906, price is now $747 per person
$747
per person
Nov 6 - Nov 10
found 3 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.
No microwave available! Even an area in the lobby to have one would be helpful.
Reviewed on Sep 3, 2026
Western Executive Inn
Price was $621, price is now $546 per person
$546
per person
Nov 6 - Nov 10
found 3 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Place was nice, staff helpful, located close to everything you’d need
Reviewed on Sep 6, 2026
Super 8 by Wyndham Billings
Price was $816, price is now $722 per person
$722
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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 First Interstate Arena at MetraPark and Amend Park are located nearby.
Beartooth Hideaway Inn and Cabins
Price was $721, price is now $655 per person
$655
per person
Oct 22 - Oct 26
found 1 hour ago
Roundtrip flight included
Chicago (ORD) to Billings (BIL)
Stay at this hotel in Red Lodge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lake Fork Trail and Montana Candy Emporium are located nearby.
Average st best. Whole town is overpriced for what you get.
Reviewed on Sep 6, 2026
Locomotive Inn
Price was $785, price is now $741 per person
$741
per person
Oct 15 - Oct 19
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Nice place next to interstate close to food n gambling
Reviewed on Sep 6, 2026
Montana Trailhead Inn
Price was $721, price is now $688 per person
$688
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Roundup Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Roundup 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.
Wed, Oct 7 - Mon, Oct 12
AZA
Phoenix - Mesa Gateway
BIL
Logan Intl.
$272 Roundtrip, just found
$272
Roundtrip
just found
Tue, Oct 27 - Tue, Nov 3
DEN
Denver Intl.
BIL
Logan Intl.
$303 Roundtrip, just found
$303
Roundtrip
just found
Tue, Oct 13 - Tue, Oct 20
PHX
Sky Harbor Intl.
BIL
Logan Intl.
$366 Roundtrip, just found
$366
Roundtrip
just found
Tue, Oct 6 - Tue, Oct 13
DFW
Dallas-Fort Worth Intl.
BIL
Logan Intl.
$392 Roundtrip, found 4 hours ago
$392
Roundtrip
found 4 hours ago
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