Want beautiful beaches and New England charm? Head to Connecticut, Maine or Massachusetts. Dreaming of the desert? We’d suggest Arizona. But if your idea of a perfect getaway entails peace, quiet, diverse scenery, rugged adventures and plenty of room to roam, it’s got to be Montana. Where else can you pack the Rocky Mountains, the Great Plains, Glacier National Park, Yellowstone National Park and Flathead Lake into one trip? The answer is literally nowhere. Besides the vast swathes of untouched wilderness, the fourth-largest U.S. state also has many world-class ski areas and historic Gold Rush-era communities. Sure, Montana technically earned the moniker the Treasure State because of its rich mineral reserves, but, from where we’re sitting, that name could have easily been bestowed by some traveler who spent a few weeks hiking, horseback riding and eating home-cooked food in one of the many charming small towns in Big Sky Country.
The 13 Most Charming Small Towns in Montana
1. Whitefish, Montana
If you’re only familiar with one vacation destination in Montana, it’s undoubtedly Whitefish—and there’s a reason for that. Not only is it the ultimate basecamp for exploring Glacier National Park, but also among the best ski towns in the U.S. and an incredible place to spend a Christmas vacation. In the winter, travelers flock to Whitefish Mountain Resort for skiing and snowboarding. And it’s always a good time to go fly-fishing. Check out accommodation options in Whitefish, Montana.
Rental to check out: Hidden Moose Cabin (8 guests): $355/night
2. West Yellowstone, Montana
Yellowstone National Park has many entry points, however, West Yellowstone gets top billing for proximity—which is ideal when you’re trying to put every precious moment toward geysers, forested trails, rivers, canyons and spotting elk. This southern Montana town also offers restaurants, shops, galleries and the Grizzly & Wolf Discovery Center, a not-for-profit wildlife park where visitors can see (you guessed it) bears and wolves. Check out accommodation options in West Yellowstone, Montana.
Rental to check out: Montana Cabin (4 guests): $275/night
3. Choteau, Montana
Forests, plains, peaks and ranches surround Choteau (pronounced shoh-toh), an agrarian town located approximately 20 miles east of the Rocky Mountains. Whether you choose to go hiking and peep wildlife in Glacier National Park, drive the Going-to-the-Sun Road or watch a rodeo, there’s never a dull (or anything short of scenic) moment in the county seat of Teton County. Check out accommodation options in Choteau, Montana.
Rental to check out: Remodeled Cottage (5 guests): $89/night
4. Libby, Montana
The best part about Libby? Most people would likely say the beautiful scenery. Majestic mountains and the Kootenai River don’t just bank this town in the northwest corner of Montana points for being pretty but also make it a fantastic springboard for rugged outdoor adventures, from hiking backcountry trails in Kootenai National Forest to trout and sturgeon fishing. Check out accommodation options in Libby, Montana.
Rental to check out: Riverside Cabin (6 guests): $208/night
5. Big Sky, Montana
Avid skiers are no doubt already chummy with Big Sky Resort. For everyone else, let us introduce you to Big Sky, a year-round mountain community in the Rockies that’s beloved for its slopeside activities and accommodations. Not much of a piste person? When the weather warms up (even just a few degrees), Gallatin National Forest is great for hiking, camping and wildlife watching. You can also go kayaking, whitewater rafting and fly-fishing on the Gallatin River. Check out accommodation options in Big Sky, Montana.
Rental to check out: Alpenglow Retreat (9 guests): $307/night
6. Livingston, Montana
The northern gateway to Yellowstone National Park, Livingston is a picturesque mountain town that counts many A-listers as frequent visitors and even part-time residents. It must be all that fresh alpine air, breathtaking views of Livingston Peak, preserved 19th-century buildings and outdoor recreation that lures the likes of John Mayer and Jeff Bridges. Check out accommodation options in Livingston, Montana.
Rental to check out: Modern Bungalow (6 guests): $216/night
7. Polson, Montana
Perched on the southern end of Flathead Lake, the largest freshwater lake west of the Mississippi, Polson provides ample opportunities for boating, paddle boarding and fishing. Even if you don’t catch anything, you won’t go hungry thanks to a handful of tasty restaurants in town. Summertime visitors should save room for juicy locally grown cherries. Check out accommodation options in Polson, Montana.
Rental to check out: Lakefront Oasis (6 guests): $200/night
8. Anaconda, Montana
A high-altitude playground for adventure, Anaconda is in prime position for travelers who want access to the surrounding mountains. When you need a break from all the peaks, cliffs and rock formations (that could happen, right?), downtown beckons with its historic Western facades and 585-foot brick tower that provides a glimpse into the town’s rich copper smelting past. Check out accommodation options in Anaconda, Montana.
Rental to check out: Newly Remodeled Nye's Place (4 guests): $78/night
9. Hamilton, Montana
Looking for a convenient pit stop—that’s also a destination in its own right—on Highway 93? Consider Hamilton. Gear up to do some hiking (Trapper Peak is one of the most popular trails in the state), walk around downtown, take in some of the historic sights, get a good meal and catch some zzzs at a log cabin or solar-powered house before hitting the road again. Check out accommodation options in Hamilton, Montana.
Rental to check out: The Lookout Tower (5 guests): $345/night
10. Phillipsburg, Montana
Philipsburg basically marks the halfway point between Yellowstone and Glacier National Parks. That’s far from the only reason to pull over at this former 19th-century mining town. Sapphires helped put this place on the map. Today, visitors can pan for brilliant blue stones at local gem shops. We’d also recommend hitting the hiking trails and grabbing a beer at Philipsburg Brewing Co. Check out accommodation options in Phillipsburg, Montana.
Rental to check out: The Douglas Creek Cottage (5 guests): $126/night
11. Big Timber, Montana
Backed by the Crazy Mountains, Big Timber is a great example of a town that really lets nature shine. It should come as no surprise that outdoor adventure abounds. Fly fishing probably just edges out hiking as the most popular pastime (though, the many trekkers who tackle Big Timber Creek Falls each season might dispute that fact). Oh, and don’t leave without visiting the Crazy Mountain Museum. Check out accommodation options in Big Timber, Montana.
Rental to check out: Bunkhouse With Horse Corrals (5 guests): $150/night
12. Stevensville, Montana
Another worthwhile stop along Highway 93? Stevensville in Bitterroot Valley. Established by Jesuit missionaries in 1841, it’s recognized as the first permanent non-indigenous settlement in Montana. Of course, you should check out the historic stuff like St. Mary's Mission and the Stevensville Museum. But, fair warning, it’s sort of hard to focus on anything other than the amazing mountain views. Check out accommodation options in Stevensville, Montana.
Rental to check out: Three-Bedroom Bungalow (6 guests): $206/night
13. Fort Benton, Montana
Benton dates back to 1846 (that’s 43 years before Montana even became a state). Its advantageous location along the Missouri River made it important for westward expansion. So, obviously, it’s brimming with history—which visitors can see firsthand thanks to the preserved old buildings, statues and museum exhibits. Of course, there’s also outdoor action in the form of hiking and canoeing. It is still Big Sky Country after all. Check out accommodation options in Fort Benton, Montana.
Hotel to check out: Grand Union Hotel (2 guests): $155/night
