When the World Slows Down: A Winter Escape to the Driftless
Sometimes the Best Getaway Is the One Where You Don't Have to Do a Thing.
There's something special about arriving somewhere and feeling your shoulders finally relax. The busy schedules, endless to-do lists, and everyday stress suddenly seem a little farther away.
That's the feeling we want you to experience at Driftless Destinations.
Tucked into the beautiful bluffs of McGregor, Iowa, our spacious, dog-friendly vacation home is a place to slow down, reconnect, and enjoy the people who matter most.
Whether you're gathering with family for the holidays, escaping for a quiet weekend with someone special, or bringing your favorite four-legged companions along for the adventure, winter in the Driftless offers something wonderful.
And sometimes, the best part of getting away isn't everything you do. It's finally having the time to do absolutely nothing.
Your Getaway, Your Way
Some vacations are about seeing and doing everything. Others are about finally having time for each other.
At Driftless Destinations, you can spend an entire weekend without ever needing to leave the house.
Challenge the family to a game of pool, air hockey, foosball, or darts. Gather around the table for cards and board games. Make popcorn, pick a movie, and settle in for an evening together.
With four bedrooms, two comfortable living areas, and plenty of room to spread out, everyone can enjoy the getaway at their own pace.
And yes, bring the dogs! They're part of the family, too.
A Little Winter Magic Beyond the Front Door
If you're in the mood to explore, winter brings its own special charm to the Driftless Region.
Wander through the shops of McGregor and Prairie du Chien, enjoy a leisurely meal at a local restaurant, or discover holiday lights and seasonal celebrations throughout our river towns.
When the snow arrives, bundle up for some outdoor fun, build a snowman, or simply enjoy the peaceful beauty of the bluffs.
And if Mother Nature doesn't cooperate? There's still plenty to discover, from shopping and bowling to indoor family activities.
The best part is knowing you have a warm, welcoming place to return to.
Come as You Are. Leave Feeling Restored.
You don't need an elaborate itinerary to make wonderful memories.
Sometimes all it takes is good food, laughter, a little friendly competition, and time together without the usual distractions.
Whether you're planning a December family gathering, a post-holiday January escape, or a weekend away with your favorite person and your dogs, we'd love to welcome you.
Your place to gather in the Driftless is waiting.
Explore winter availability at Driftless Destinations in McGregor, Iowa.
Experience the Holiday Magic of the Driftless 🎄
Winter brings a different kind of beauty to the Driftless Region. Our charming river towns come alive with holiday lights, festive gatherings, local shopping, and traditions that make this time of year special.
Whether you're visiting with family, enjoying a couples' getaway, or making memories with the kids, there's plenty of holiday cheer to discover.
⛸️ Ice Skating & Winter Fun
Bundle up and enjoy a little old-fashioned winter fun!
A local ice-skating rink is tentatively scheduled to open November 20, weather and operating conditions permitting. It's a wonderful way to spend an afternoon or evening together before heading back to your cozy vacation home.
Be sure to check current rink hours and opening updates before planning your visit.
🎄 Festival of Trees – McGregor, Iowa
One of the wonderful ways to celebrate the season is McGregor's Festival of Trees.
Enjoy the creativity, decorations, and festive spirit that make small-town Christmas celebrations so memorable.
It's a lovely addition to a holiday weekend in the Driftless.
🎁 Holiday Arts, Crafts & Shopping
McGregor's holiday art and craft show offers another opportunity to enjoy the season while supporting local artists and makers.
And the holiday fun doesn't stop in McGregor!
Explore seasonal markets, decorated storefronts, unique boutiques, and special events in neighboring communities, including Marquette, Prairie du Chien, Elkader, and other Driftless towns.
You might even find a few one-of-a-kind Christmas gifts along the way.
✨ Twinkle Light Village – Viroqua, Wisconsin
For those who enjoy exploring a little farther, Twinkle Light Village at Wild West Grounds in Viroqua offers another festive holiday outing.
December 4–5, 2026
Friday: 4–7 PM
Saturday: Noon–6 PM
Admission is free, with Santa visits and sleigh rides scheduled for Saturday from 2–5 PM.
❤️ The Best Part? Coming Back Together.
After a day of exploring holiday festivities, return to Driftless Destinations for an evening of your own.
Make hot chocolate, gather around for games, enjoy a Christmas movie, or prepare a favorite family meal.
There's no rushing from one activity to another and no pressure to fill every minute.
Just a beautiful place to gather, relax, and enjoy the people you love.
Sometimes the simplest moments become the memories we treasure most.