Planning a getaway with a group of friends, a family reunion, or a multi-generational ski trip? Big Sky, Montana offers the perfect mix of natural beauty, adventure, and luxury; and when you’re traveling with a crowd, space and comfort matter.
At Wilson Peak Properties, we have a number of premium Big Sky vacation rentals designed for larger groups. Our holiday rentals in Big Sky offer spacious layouts with high-capacity homes offering 4 to 7+ bedrooms, expansive living areas, and upscale amenities, you’ll find everything you need to gather, relax, and make lasting memories in the mountains.
Why Book a Large Vacation Rental in Big Sky?
Whether it’s a holiday gathering or a week-long ski trip, our holiday rentals in Big Sky provide the space and comfort groups need. Hotels and standard condos rarely offer enough space or privacy. That’s where large vacation rentals shine.
Big Sky group rentals from Wilson Peak Properties feature:
- Spacious open-concept living and dining areas
- Gourmet kitchens with seating for large groups
- Private hot tubs and mountain views
- Multiple suites and bunk rooms
- Ski-in/ski-out access (available in select homes)
- Game rooms, fireplaces, and home theaters
Our homes are designed to bring people together without sacrificing comfort or style.
Ideal for Every Occasion
Holiday Rentals in Big Sky
Celebrate the season in the mountains with an amazing holiday rental in Big Sky and nearby. Enjoy Thanksgiving dinners around a custom dining table, decorate the tree next to a roaring fireplace, and wake up to snow-covered peaks on Christmas morning. Our properties offer the perfect setting for festive gatherings.
Family Reunions
Reconnect in comfort. With ample bedrooms, indoor and outdoor gathering spaces, and easy access to Big Sky’s trails and rivers, our homes make hosting a family reunion simple and memorable.
Ski & Hiking Trips with Friends
After a day on the slopes or trails, return to a home where your group can unwind, cook together, and share stories by the fire or on the back porch. Many of our properties are minutes from the trails and lifts and some are even ski-in/ski-out.
Featured Big Sky Rentals for Large Groups
Below are a few of our most popular homes ideal for 8 or more guests:
Alpenglow Retreat 
- Sleeps: 13
- Bedrooms: 5 | Bathrooms: 4.5
- Features: Easy access to Yellowstone and Big Sky Resort! Gorgeous sunsets off the front deck!
- Ideal for: Holiday gatherings, group ski trips
Curley Bear Lodge
- Sleeps: 14
- Bedrooms: 5 | Bathrooms: 3
- Features: On the golf course, large window view, privte hot tub
- Ideal for: Golfing groups, friends & family
White Wolf Retreat
- Sleeps: 16
- Bedrooms: 7 | Bathrooms 4.5
- Features: Covered deck, private hot tub, 5 minutes to slopes
- Ideal for: Family reunions or multi-generational groups
Need help choosing the perfect home? Contact Our Team for personalized recommendations.
Group-Friendly Amenities
All of our large group rentals include luxury features that enhance your stay:
- Dining tables and kitchen seating for 10+
- Dual living areas or loft spaces
- Ski and equipment storage
- Multiple decks with outdoor seating
- In-home laundry
- Fast Wi-Fi and smart TVs
- Optional concierge services, including private chefs and grocery stocking
Some homes also feature additional perks like theater rooms, game tables, and separate guest quarters.
When to Book Big Sky Group Lodging
Winter & Holidays
For Christmas, New Year’s, or President’s Day weekend, book well in advance — especially for larger homes. Many groups plan these trips a year out.
Summer
June through August is ideal for reunions, milestone birthdays, and outdoor adventuring. The weather is perfect for rafting, hiking, and day trips to Yellowstone.
Fall & Spring
These shoulder seasons offer great rates and mild weather. They’re perfect for group retreats, workshops, or quiet escapes with friends.
Availability for holiday rentals in Big Sky fills quickly, especially for Christmas and New Year’s.
Why Wilson Peak Properties?
With a portfolio of hand-selected homes and unmatched local service, Wilson Peak Properties is the trusted choice for high-end lodging in Big Sky.
- Locally managed with 24/7 guest support
- Expertly maintained, clean, and professionally styled homes
- Flexible booking options and direct communication
- Concierge services available upon request
Whether you’re bringing 8 or 18, we ensure your group has an unforgettable stay.
