With nicknames such as “The Last Best Place” and “Treasure Country,” Montana is an amazing state to visit. The state is packed with history dating back to the Gold Rush and boasts breathtaking natural scenery anywhere you look. Bordering Yellowstone National Park’s northern side and home to Glacier National Park, which passes directly into Canada, Montana is an ideal choice for a romantic weekend getaway for anyone who loves the outdoors. Many of the vacation rentals in Montana are situated just minutes away from outdoor recreation, historic architecture, museums, and much more. The state is also known for its friendly residents and down-home charm. If you’re planning to surprise your special someone with a trip to “Big Sky Country,” consider one of these top eight locations to ensure an amazing weekend.

1. Billings

Billings is one of Montana’s largest cities, making it a good option if you’re looking for a combination of city life with the charm of a small town. Vacation rentals in the area offer lovely views of the sandstone cliffs above the Yellowstone River and Pictograph Cave State Park, and there’s plenty to do and see to keep you entertained during your weekend getaway. Start your adventure with a visit to the Moss Mansion, a 1901 European-style home once owned by Preston Boyd Moss, the developer of the Billings Light and Power Company. Next up, enjoy an afternoon date at Zoo Montana, home to almost 100 animals of 58 separate species. When you’re ready for an intimate meal, pop over to Ciao Mambo for some Italian food and wine, served in an art-filled dining room.

Find vacation rentals in Billings

2. Columbia Falls

Columbia Falls sits surrounded by the lush greenery of the Flathead National Forest, where you can hike the trails, relax by the lake, and even spot a few grizzly bears in the distance. Marantette Park holds live music concerts during the summer months, and Glacier Jeep Rentals makes it easy to explore the terrain of Glacier National Park. For a unique indoor date, visit Montana Vortex and House of Mystery, a unique fun-house style shack filled with optical illusion mirrors and mazes.

Find vacation rentals in Columbia Falls

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!

3. Great Falls

Great Falls is one of Montana’s most popular cities to visit, as it truly has something for everyone. From American history to beautiful works of art, there’s plenty for happy couples to do and see while enjoying the natural scenic beauty of the land. Spend the day at Paris Square Museum and view beautiful works representing the American West, then head to the Lewis and Clark National Historic Trail Interpretive Center for a view of the actual route the explorers took through Giant Springs State Park. For a glimpse of the shortest river in the world, check out the Roe River in the Madison Aquifer. When you’re finished exploring, stop by Mackenzie River Pizza Co. for some of the best pie in town.

Find vacation rentals in Great Falls

4. Helena

Established in 1864 as a gold campsite during the Gold Rush, Helena serves as Montana’s state capital and sits between Yellowstone National Park and Glacier National Park. Helena has plenty to offer for visiting couples, ranging from relaxing yoga at Hot Yoga Helena to pony rides at Sanford Family Farm. For a fun night with a hint of Gold Rush history, visit the Windbag Saloon and Grill, a popular local watering hole housed in a vintage saloon.

Find vacation rentals in Helena

5. Livingston

If you’re looking for a spot with a welcoming small town atmosphere and plenty of outdoor activities, book a vacation rental for the weekend in Livingston. Located on the Yellowstone River north of Yellowstone Park, Livingston is rich in history and offers gorgeous natural scenery at every turn. The Livingston Depot was built in 1902 as a railway depot and features exhibits of the town’s railway system, while the Yellowstone Gateway Museum houses artifacts from Yellowstone National Park. For a fun date, visit Fancy’s Sips and Sapphires, where guests enjoy tasty beverages while panning for authentic sapphires.

Find vacation rentals in Livingston

6. Whitefish

Whitefish is located near the northern Rocky Mountains just minutes from the Whitefish Mountain Ski Resort. This gateway to Glacier National Park is the perfect choice for a winter or summer weekend getaway. Hit the slopes at the resort, or go mountain biking on Whitefish Trail if you’re visiting during the warmer months. If you’re up for some couples relaxation, visit the Spa at Whitefish Lake and indulge in a massage for two or a soothing mud bath. For a warm and cozy intimate dinner, make a reservation at Whitefish Lake Restaurant, where the decor resembles a log cabin.

Find vacation rentals in Whitefish

7. Three Forks

Three Forks sits at the forks of the Madison, Jefferson, and Gallatin rivers, with a rich history and gorgeous views of Yellowstone and Glacier National parks in the distance. Three Forks is also home to Sacagawea Park, a memorial park honoring the interpreter and guide for the Lewis and Clark expedition and her time spent in the town. For some more local history, spend a day at the Headwaters Heritage Museum and check out the railroad artifacts, fur trading exhibits, Native American art, and Lewis and Clark memorabilia. If you’re an adventurous couple, Skydive Three Forks offers tandem skydiving excursions for all skill levels. When you’re ready for a quiet, romantic meal after all that excitement, head over to Main Street and visit the Three Forks Cafe.

Find vacation rentals near Three Forks

8. Red Lodge

Choosing a vacation rental in Red Lodge puts you at the gateway to Yellowstone National Park via the Beartooth Highway, making this quaint town a great choice if you want to spend an afternoon in nature. If you’re visiting Red Lodge during the winter months, Red Lodge Mountain resort offers plenty of white powder for skiing and snowboarding. Beartooth Wagon and Sleigh Rides host fun horse-drawn sleigh and carriage rides year-round perfect for couples. For a hearty steak after a day of recreation, stop by Carbon County Steakhouse for a great meal and some cowboy-themed ambiance, then enjoy a beautiful Montana sunset from your vacation rental.

Find vacation rentals in Red Lodge


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