Get the most out of your Montana vacation by skiing at 2 of the best resorts and splitting your stay between 2 Stay Montana vacation rentals!
Skiing is a big part of winter recreating in Montana. It is the perfect way to get outside and see the spectacular Montana mountains! Split your stay at Big Sky Resort and Whitefish Mountain Resort for the ultimate winter ski vacation! This is the perfect opportunity to road trip across Montana and see the sights and Stay Montana offers a variety of lodging options in Big Sky and Whitefish.
Big Sky Resort – Big Sky Resort is known as the “Biggest Skiing in North America” with over 5,850 skiable acres! In addition to the fabulous skiing at the resort, Big Sky also has a wonderful Town Center with fantastic restaurants, shopping, a movie theater and more! Plus, don’t miss out on all the other fun winter activities including Nordic skiing, snowshoeing, snowmobiling, sledding and much more! Find the vacation rental of your dreams to call home while on vacation!
Find the Big Sky vacation rental of your dreams to call home while on vacation! – Big Sky Ski Vacation Rentals
Whitefish Mountain Resort – Whitefish Mountain Resort was recently ranked #3 Resort in the West by Ski Magazine Readers! With 3,000 skiable acres and 14 lifts, the resort offers terrain for everyone. The views of “Big Mountain” as the locals call it, are absolutely stunning as you enter Whitefish. Bring your ski gear and hit the slopes!
The town of Whitefish has a lot to offer in the winter months. Enjoy ice fishing, snowshoeing, snowmobiling, fat tire biking, shopping, and dining at local restaurants!
What’s the best way to get from Big Sky Resort to Whitefish Mountain Resort?
There are many sights to see along this scenic drive so make sure you take your time and enjoy! If you are doing a round trip, we recommend taking the Seeley Lake route one way and the Eastside of Flathead Lake route the other way. The landscape is breathtaking and will not disappoint! Make sure to check road conditions before you head out.
Whitefish Mountain Resort was ranked #6 on the list while Big Sky Resort was ranked #28! How cool is that?!
Big Sky is known as the “Biggest Skiing in North America” with over 5,850 skiable acres while Whitefish Mountain Resort has right around 3,000 skiable acres. Both resorts are the ski enthusiasts’ dream! Plus, both Big Sky and Whitefish are fun resort towns with lots of things going on for you to enjoy in the evening or if you’re looking for activities beyond skiing.
To gear you up, we’ve put together a list of must-haves for you to pack on your ski trip to Montana! We’ve listed everything you’ll need on your trip and a few extras that you may not have thought of! Remember to check the weather report before traveling to Montana as temperatures and ski conditions can vary.
Ski & Snowboard Clothing
- Thermal Base Layer – Top & Bottom
- Fleece Mid-Layer
- Waterproof Ski Jacket
- Waterproof Ski Pants
- Multiple Accessories – Hats, Waterproof Mittens or Gloves, Ski Masks, Socks
Ski & Snowboard Gear
- Skis or Snowboard with Bindings
- Ski Boots or Snowboard Boots
- Ski Poles
If you do not have the appropriate ski gear, we partner with Ski Butlers in Big Sky to bring you the best ski equipment delivered right to you!
Non-Ski/Snowboard Clothing – “Mountain Casual”
- Warm Winter Jacket
- Winter Boots (Waterproof boots are recommended)
- Jeans (Insulated jeans help keep the chill at bay, but regular jeans will do just fine)
- Sweaters or Fleeces
- Multiple Pairs of Warm Socks
- Warm Sleepwear (Flannel is a great choice!)
- Swim Suit! If your rental has a hot tub!
- Lip Balm with SPF
- Shaving Supplies
Electronics & Misc.
- Lift Tickets/Passes
- Wallet with ID
- Cell Phone
- Charging Cords for All Devices
- Prescriptions/Vitamins/Other Wellness
- Water Bottle(s)
- Toe & Hand Warmers
Looking for a place to stay? Check out these ski-in/ski-out properties!
Fall Activities & Weather!
Fall in Montana is simply magical. From leaves changing colors, to fall festivals, to spending time outdoors, there’s something for everyone to enjoy this autumn!
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Flathead Valley (Whitefish & Bigfork)
Great Northwest Oktoberfest – 2 GREAT WEEKENDS! September 28–30 & October 5-7. Enjoy delicious German food, drinks, music and dancing, crazy contests, food trucks, artists, crafters and so much more! Stay Montana is proud to be one of this year’s premier sponsors of Oktoberfest in Whitefish! All of our Stay Montana guests that are attending Oktoberfest will be offered free entrance tickets!
Get a pumpkin spice latte and stroll Downtown Whitefish – Downtown Whitefish is particularly charming in the fall as the colors change and the air becomes crisp. It’s the perfect time to explore, shop, dine and enjoy a pumpkin spice drink!
Visit the Conrad Mansion The Conrad Mansion is in Downtown Kalispell and was built in 1895. It gives us a glimpse into the life of early pioneers in Montana! This home is magnificently well maintained and makes you feel like a person from the past as you tour!
Visit Glacier National Park – GNP is a hidden fall gem. Tourist traffic tends to decline in the fall making it the perfect relaxing, nature getaway! The leaves in the park change colors and make for a very magical experience! Bike the Going-to-the-Sun Road, hike one of the many trails (we like the Apgar Lookout Trail), take a boat tour on Lake McDonald, and so much more!
Play a round of golf – Golf at Whitefish Lake Golf Club through October!
Make your way through a corn maze – Fritz Corn Maze is a Kalispell staple for fall activities! Tour the maze, haunted barn and even catch a drive-in movie!
Pick your own pumpkins at a pumpkin patch – Sweet Pickin’s Pumpkin Patch in Kalispell. Not only are there pumpkins, Sweet Pickin’s offers giant jumping pillows, a petting zoo, an apple cannon, kettle corn and more fun fall activities!
Need a place to stay? Check out our Flathead Valley properties!
Bozeman & Big Sky
Visit Yellowstone National Park – Yellowstone is a beautiful fall destination as tourists thin out and the foliage changes colors. Go wildlife watching, take a hike, go for a bike ride, or do some fall fishing!
Haunted Peaks Halloween Festival (Big Sky Town Center, End of October) – Enjoy live music, the Dia De Los Muertos celebration, a costume block party, a horror film festival, Yappy Hour costume party for people and their pets, a haunted run to the pub, Pumpkin King & Queen carving competition, and many more festive, fall activities!
Visit Rocky Creek Farm in Bozeman and pick your own pumpkins! Take your little ones to pick our their own pumpkins and enjoy fall activities! Plus, they offer fall festival farm visits where you can reserve a time to bring your family.
Bozeman Maze (October) – The maze is an autumn staple in Bozeman. Enjoy the 5000 bale maze, concessions, powerjump bungee trampoline, hay rides, pumpkins, and much more with the whole family!
Catch a Bobcat home football game – You wouldn’t get the full Bozeman experience if you didn’t attend a Bobcat football game! Enjoy not only the game itself, but tailgating before the game and celebrations around town when they win!
Take a hike and enjoy the fall colors! – Ousel Falls Trailhead in Big Sky is one of our favorites!
Fall Weather in Montana
The weather in Montana tends to be more mild in the Fall months. September is a bit of a transitional month where it has warmer, sunny days in the 60s and 70s and cooler nights in the 30s and 40s.
October feels the most like fall with temps in the 50s and 60s during the day with lots of sun as the leaves change colors. The evenings really start to cool off and make for great sweater weather!
November is definitely more chilly as we start to see some snow in higher elevation areas, but don’t pack your fall sweaters too soon, there are still some warmer days here and there!
Check out our local team’s favorite picks for summer in Montana!
Montana summers are legendary! In the winter, parts of Montana can get a lot of snow but in the summer Montana turns into an outdoorist’s dream playground. Did you know it stays light past 9pm or even 10pm in some Montana locations during summer?!
We’ve put together a list of our favorite summer activities by area for you and your family and friends to enjoy on your vacation to Montana!
- Book a Montana Whitewater Rafting trip
- Go on a flyfishing adventure
- Enjoy horseback riding
- Check out the Big Sky Farmer’s Market
- Hike to the gorgeous Ousel Falls
- Golf at the Big Sky Resort Golf Course
- Eat at Bunker Deck & Grill
- Take a scenic lift ride
- Enjoy numerous basecamp activities
- Mountain biking
- Take a guided hiking tour
- Embrace your inner Hawkeye and try out archery
- Play a round of mini golf
- Search for Creature X experience
- Book a park tour
- Mountain Biking
- Drive through Firehole Canyon Drive for spectacular views of lava flows and a fun place to swim!
- Visit Old Faithful and the Upper Geyser Basin
- Hiking – There are numerous trails, find the best one for you!
- Visit the Grizzly and Wolf Discovery Center
- Check out the town of West Yellowstone for touristy attractions and a bite to eat
- Big Sky Country State Fair – Starts around July 20th
- Wander through Bogert Farmer’s Market
- Check out Music on Main – Free every Thursday evening in Downtown Bozeman
- Go on a river tubing trip on the Madison River
- Visit the Museum of the Rockies
- Bozeman and Big Sky are neighboring cities, check out the above section for more summer favorites!
- Boat or swim on Flathead Lake or Whitefish Lake
- Visit Whitefish Mountain Resort for their summer offerings, including ziplining, mountain biking, and scenic chair lift rides
- Hiking – check out the Whitefish Legacy Trail System or hike up Whitefish Mountain Resort and take the chairlift or gondola down
- Spring Biking in Glacier National Park
- Hot Spring Tours – There are lots of Hot Springs around Montana!
- Golfing – Golf season starts around May and runs through October (weather permitting)
- Have a brew at the Bonsai Brewing Project in Whitefish or Flathead Lake Brewing Company in Bigfork
- Biking on the Going to the Sun Road
- Visit the beautiful Lake McDonald – it’s a little chilly, but worth it to dip your toes in!
- Hiking on numerous trails – Our favorite: Avalanche Lake Trail at Lake McDonald
- Check out the West Glacier Village for shops and dining!
- Play a round of mini golf at the Golfing to the Sun mini golf course
- Go on a Glacier Zipline Canopy Tour
What our guests are saying about us!
At Stay Montana we value guest feedback and pride ourselves on excellent customer service. We hope that every guest that stays at one of our properties has a fantastic time enjoying the wonders of Montana while staying in the comfort of a Stay Montana vacation home. We are a local, family & emoployee-owned company that is always striving to improve. We love hearing what our guests have to say about their stay so we can keep getting better! And we REALLY love getting raving reviews like the one below!
“We had the best time at this place. Our only negative is that we didn’t have more time to stay longer and use the property to its full potential. Our stay was in early June and the scenery was breathtaking. The house was very clean and had everything we needed.” – Austin, a Stay Montana Guest
We’re delighted Austin had such a wonderful stay and we hope he can stay longer next time! Austin stayed at Le Ciel in Gallatin Gateway, between Bozeman and Big Sky. Le Ciel is a beautiful 2 bedroom, 2 bathroom home with breathtaking , 360° views and Gallatin river access. You’ll see why Montana has been named “Big Sky Country” in this home, the skies are massive and go on for days!
Top 5 Ski-In/Ski-Out Properties in Whitefish! ⛷
Whitefish is a year-round destination, but it seems to come alive in the winter and really is the ski enthusiast’s dream! It is home to Whitefish Mountain Resort that sits atop what is affectionately known by locals as “Big Mountain” with 3,000 skiable acres and 14 lifts. The Resort was even recently named #3 Resort in the West by Ski Magazine readers.
Get your lift tickets ahead of time to ensure the best rates possible!
If you plan to spend all day/everyday on the slopes, a ski-in/ski-out home can turn your ski adventure into the trip of a lifetime! Hit the slopes right from your backdoor or watch the skiers go by while you have a cocktail in your downtime!
In the evenings, make sure to check out the town of Whitefish for some local flavor. There lots of local shops, restaurants, breweries, and much more to enjoy while you’re on vacation. Whitefish even offers a FREE snow bus that will shuttle you around town and up to the mountain. No need to rent a car!
Make sure to pack your ski gear and check out our top 5 Whitefish Ski-In/Ski-Out properties and plan your winter getaway!
Bozeman, MT is a magical place in the winter. There are so many fun activities to enjoy with loved-ones. We’ve put together a list of our top 5 favorite winter activities that we love to do in Bozeman!
1. Skiing/Snowboarding: This one is a no-brainer. There are two fantastic ski areas in immediate proximity to Bozeman and the greater Gallatin Valley. Bridger Bowl is a local favorite for ski days and has 2,000 acres of terrain, 8 chair lifts, 2,500 vertical feet, 3 lodges. Big Sky Resort is 45 minutes – 1 hour from Bozeman and is definitely worth the drive. With 5,850 acres of terrain to explore, Big Sky Resort is known as “The Biggest Skiing in America”.
2. Hot Springs: Escape the cold and take a dip in the natural hot springs that surround Bozeman. Bozeman Hot Springs has 12 different pools to enjoy just 15 minutes outside of the city. This is the perfect place to relax and warm-up after a fun-filled day of skiing.
3. Cross-Country Skiing/Nordic Skiing: The Bozeman community is recognized as a top cross-country ski destination! There are 3 main Nordic ski areas:
- Crosscut Mountain Sports Center near Bozeman.
- Lone Mountain Ranch near Big Sky. Named Cross Country Skier magazine’s #1 Nordic ski destination in North America with 85 km of trails through wooded trails and mountainous terrain.
- Rendezvous Ski Trails near West Yellowstone.
5. Stroll Downtown: Downtown Bozeman has the most beautiful holiday decorations. It’s a dream to stroll downtown with a coffee or hot cocoa in hand and admire the beautiful Christmas lights. Stop in any of the boutiques and local shops to warm up and support a local business!
6. Ice Skating: Take the kids or go on a fun date-night with your partner to the ice skating rink! There are 3 public ice skating rinks in Bozeman. Southside Park, Beall Park and Anderson Pavillion at Bogert Park are open starting around Christmastime.
Check out our Bozeman and Gallatin Gateway vacation rentals and start planning your winter vacation!
Our Stay Montana leadership team had the awesome opportunity to have a team building leadership retreat and attend the Vacation Rental Management Association (VRMA) conference in Vegas this year. They were able to bond as a team as well as learn from top industry professionals in the vacation rental world.
The team had their leadership retreat from Friday-Monday and they had a blast! They were able to have meetings poolside (dreamy), some amazing team bonding dinners at fantastic restaurants and even got to attend an America’s Got Talent show!
The Vacation Rental Management Association (VRMA) conference that followed the leadership retreat was a success! Being in Vegas live with other professionals who are so passionate about the vacation rental industry was a highlight of the trip. Our team was able to meet folks we’ve only previously spoken to over phone/email in-person and that time was so valuable for building relationships & learning from other professionals.
2022 Great Northwest Oktoberfest was a success!
Stay Montana attended and sponsored 2022’s Great Northwest Oktoberfest in Whitefish, MT for 2 weekends! We met so many nice folks and had so much fun getting to know locals and out-of-towners who made the trip to attend the fest! The food was delicious, the authentic German drinks were flowing, the music was catchy, and the weather was beautiful (for the most part)!
Huge thanks to our Bozeman team for making the trip to help out on the first weekend! We couldn’t have done it without you!
We can’t wait to see you all next year!
Stay Montana is excited to announce that we’re finalists in the 2022 Gallatin’s Greatest in the following categories:
⭐️Best Employee Recognition Program
⭐️Most Innovative Workplace
⭐️Best New Business
We are especially excited to be recognized in these categories as we pride ourselves on team building and having a company culture that empowers our employees. Additionally, we are always looking for new technology and software to innovate our day-to-day processes for our valued team, guests and owners.
Thank you to the Bozeman and surrounding communities for your support and for voting for Stay Montana! We appreciate you! We are proud and thankful for this recognition.
Who is Stay Montana?
We are a local, family & employee-owned boutique vacation rental company specializing in making Montana memories. We strive to provide the best customer service possible and continually exceed guest & owner expectations. We even provide our family recipe, Ella Cookies, at check-in. Our guests & owners love them!
Come visit! We’d love to welcome you to Montana! Check out our Bozeman Vacation Rentals.
Looking for a property management company in the Bozeman area? We’d love to partner with you! Please visit our Property Management page to learn more and contact us!