When you plan a winter bachelor party in Montana, you can look forward to hanging out with the guys while skiing the slopes in Big Sky, or soaking up the nightlife and breweries in Bigfork. During the warmer seasons, hike through Yellowstone National Park or another scenic wilderness area. Make way to Flathead Lake where you can fish and boat, or venture to the Rocky Mountains to rock climb, ski, or snowboard. Book a stay at one of numerous Montana vacation rentals for your upcoming bachelor party. Plan your celebration with these Montana cities and towns at the top of your list.

1. Big Sky

Head out with your buddies to enjoy the thrills of skiing or snowboarding down the Rocky Mountains. Big Sky is a popular vacation destination for winter activities, but it is also ideal for groups wanting to challenge themselves while mountain biking on the trails at Big Sky Resort. Head out to see the wildlife in Yellowstone National Park or host a fishing challenge near the hot springs or geysers. Nightlife in Big Sky gives you a chance to kick back and relax with your crew while rocking out to the live music at Scissorbills Saloon or while playing shuffleboard and pool at Choppers Grub and Pub.

Find vacation rentals in Big Sky

2. Livingston

Show off your hiking, running, or cycling skills when choosing Livingston as your bachelor party vacation destination with the guys. With access to Yellowstone National Park, you can spend a weekend trout fishing in the Yellowstone River, or take a guided tour with Montana Fly Fishing Guides. Head out on the water with a boat tour hosted by Rubber Ducky River Rentals before heading out for a few beers to celebrate your impending nuptials at Murray Bar. The Whiskey Creek Saloon and Liquor is a hotspot for bachelor party celebrations, or you can hang in a rustic cabin vacation rental to host a poker game with your buddies.

Find vacation rentals in Livingston

3. Whitefish

Sit back with your groomsmen when renting a vacation rental in one of the most scenic cities in the state. Whitefish features some of the best slopes to ski or snowboard when stopping in at the Whitefish Mountain Resort. If you are traveling with an athletic group, try your hand at rock climbing with Rock Climb Montana. Get in 18 holes at the Whitefish Lake Golf Club, and then participate in some bar games with some brews at the Palace Bar. Casey’s offers a woodsy, rustic environment for a night on the town with the guys, while the Great Northern Bar and Grill offers multiple TV sets to catch the big game.

Find vacation rentals in Whitefish

Find the perfect Montana vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Billings

A bachelor party week or weekend in Billings gives you a chance to reap the happy hour benefits at the Red Door Lounge, and live music at the Loft Dance Club to get the party started. When you want to explore the scenic area, head to the Ski Station to rent your snowboards before challenging your crew to a ride down the slopes. RimRocks is a great place to drop in your fishing lines while Pictograph Cave State Park gives you a chance to hike or jog during the mornings.

Find vacation rentals in Billings

5. Big Timber

Get crazy with your groomsmen when touring the Crazy Mountain Museum and exploring the Absaroka-Beartooth wilderness area near vacation rentals in Big Timber. Host an active day hiking at Natural Bridge State Park before toasting to your nuptials at the Thirsty Turtle Tavern and Grill. The Two Rivers Gallery is a great spot to get a group photo before hitting the nightlife scene in the city. Big Timber is home to the Timber Bar and Grill where you can grab some beers and enjoy some bar bites before heading back to your vacation rental with a mountain view to continue the celebration.

Find vacation rentals in Big Timber

6. Fort Benton

Fort Benton offers just the right environment for a group of guys wanting to habitat a rustic vacation rental and outdoor activities. Run or jog along the Fort Benton bridge in the morning, and then head out to see the mountains and geological formations at White Cliffs. Practice your swings when golfing 18 holes at the Signal Point Golf Club, and then relax for a bit at the clubhouse. If nightlife is what you’re looking for, the Palace Bar and the Pour House Saloon deliver with happy hour specials and tasty bar food.

Find vacation rentals near Fort Benton

7. Bigfork

Make Bigfork your vacation destination for your bachelor party and sample the local brews at the Flathead Lake Brewing Co. Pubhouse with your closest friends. The mountain city of Bigfork features an abundance of nature-driven attractions for the athletic types, such as boating on the Swan River or fishing in Flathead Lake. Head out to Glacier National Park for a hike, and then golf the afternoon away at the Eagle Bend Golf Club. The Garden Bar is the perfect spot for a nightcap before heading back to your vacation rental.

Find vacation rentals in Bigfork

Ready to go? Check out these amazing Montana vacation rentals on Tripping.com.