The Coolest and Warmest Winter Glamping Destinations

According to iges.com, the hottest travel trends this winter include digital detoxing, embracing the weather and the classic “traditional winter getaways” which means heading out of the cold and into the sunshine. Here are a few ways you can be trendy when glamping with us this winter:

Cabin at Thousand Trails Bend-Sunriver
Cabin at Thousand Trails Bend-Sunriver

Embracing the Weather: This means going to the snow and for our glampers, it means places like Leavenworth, Washington and Mt. Hood or Bend, Oregon. Book a yurt, glamping cabin or cottage at Thousand Trails Bend-Sunriver and enjoy this oft-voted “best outdoorsy town” in the country! Ski or snowboard at Mt. Bachelor, snowshoe in Deschutes National Forest, which offers several snowshoe trails, or try fat-tire biking in the snow or indoor ice skating at the Pavillion. Plan to be here to enjoy WinterFest, scheduled for February 13-15, 2026, that will include an ice carving competition, a wine walk, live music and snowsports competitions.

Mt. Hood Tiny House Village
Mt. Hood Tiny House Village

The Mt. Hood Tiny House Village is a great place to glamp when enjoying the Mt. Hood Territory in winter. Try night skiing or cosmic tubing at the Mt. Hood Skibowl, take a guided tour of Mt. Hood National Forest on a snowmobile, or a moonlight snowshoe tour around the iconic Timberline Lodge.

Winter at Leavenworth Tiny House Village
Winter at Leavenworth Tiny House Village

Leavenworth, Washington is always great in winter with opportunities for downhill skiing, Nordic skiing, sledding, snow tubing, ice fishing and a visit to a reindeer farm. Icicle Ridge Winery offers winter wine walks (icicleridgewinery.com) and the millions of twinkling lights will continue to illuminate the quaint Bavarian-style downtown through February. Book a stay at Thousand Trails Leavenworth for a great winter glamping getaway here.

Escaping the Weather: Most likely you’re heading to the sunshine. Our choices would include a colorful cottage at Encore Tropical Palms to do the theme parks or a trip to The Keys with a stay at Encore Fiesta Key or Encore Sunshine Key. EPCOT’s International Festival of the Arts runs January 16 through February 23, 2026, while the Key West Food and Wine Festival is set for January 26-February 1, 2026. South Carolina’s Myrtle Beach is an option for a glamping getaway with a stay at Carolina Shores RV Resort. Mild daytime temps and cooler nights are a nice trade-in for sub-zero snow days! Activities here can include golfing, strolling the Boardwalk, visiting the many museums or enjoying the beauty of Brookgreen Gardens in winter. On the West Coast, plan a glamping getaway to Thousand Trails Pio Pico or Thousand Trails Oakzanita Springs to explore the San Diego area in winter. Gray whales are migrating from December to April, so now is a good time for whale watching. Speaking of migrating, it is also the migratory season for thousands of birds so check out the San Diego River Estuary.

Vacation Cottages at Thousand Trails Palm Springs
Vacation Cottages at Thousand Trails Palm Springs

Digital Detoxing: This type of getaway may not necessarily mean absolutely no screens, but probably something more along the lines of being present, being in nature and really taking it all in without multi-tasking going on. Exploring national parks, taking long hikes in the forests and woodlands, walking rugged shorelines and spending quality time with friends and family is most likely the itinerary for this kind of trip. One of the best destinations for spiritual renewal may be Red Rocks State Park in Sedona, Arizona. Book a stay at Thousand Trails Verde Valley and explore the red sandstone canyonland with its healing vortexes. Another option is Joshua Tree National Park in California, another spot chock full of serene landscape vistas and energy vortexes. Book a glamping cabin or cottage at nearby Thousand Trails Palm Springs. Yosemite in winter is a wonderland with opportunities for skiing and snowshoeing at Badger Pass Ski Area and hiking the trails that remain open in winter. Book a yurt at Thousand Trails Yosemite Lakes for a great glamping getaway.

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5 Things to Do in Leavenworth, WA

If you’re heading to the ultra-charming Pacific Northwest city of Leavenworth to get in the holiday spirit, you’re in for a holiday treat. If you’re heading there for outdoor experiences, you’re still in for a treat. To start this wonderful getaway, book a cabin or a tiny house at the Leavenworth Tiny House Village, pack your snow gear and your holiday best and head to the Pacific Northwest! There’s plenty to see and do here, but we picked five things to get you started:

Leavenworth Tiny House Villlage at Christmas
Leavenworth Tiny House Village at Christmastime

1. However you celebrate the holiday season, you have to admit that reindeer, nutcrackers and snow play into any holiday theme and Leavenworth has all of that. The Leavenworth Nutcracker Museum (nutcrackermuseum.com) located in town displays nutcrackers from the 12th and 13th centuries to modern day. After you’ve explored, pick up your own souvenir nutcracker at the Nutcracker Lady Gift Shop. The Leavenworth Reindeer Farm is a great experience as well, but book soon if you’re visiting in December, because they are kinda busy in December doing reindeer stuff! With this interesting experience, you will learn about reindeer and have a chance to feed them and take pics with them. For hours and more info, visit leavenworthreindeerfarm.com.

2. A stroll through downtown Leavenworth during the holiday season will have you thinking you’ve been transported to the set of a holiday movie. Pinch yourself, this beautiful Bavarian-style city is very real, and you can experience the half a million twinkling lights, the carolers, the hot cocoa and even Mr. & Mrs. Claus! On weekends, there are strolling carolers, photos with Santa, and live performances from the Sugar Plums, an award-winning holiday choir, in the town’s gazebo. The Leavenworth Festhalle has a gingerbread house exhibition, Santa costumes from around the world, photo ops and hot cocoa and snacks.

Leavenworth, WA
Leavenworth, WA

3. Outdoor experiences here are as plentiful as the snowflakes that fall annually. Head to Lake Wenatchee State Park that offers over 30 miles of groomed trails for cross-country skiing, 12 miles of marked snowshoe trails, and a sled hill. For downhill skiing and snowboarding, check out Leavenworth Ski Hill. Other outdoor fun here includes fat biking, sledding and ski hill jumping. For details on Ski Hill, visit skileavenworth.com. Or sit back and let someone else do the work as you explore the outdoors on a sleigh ride – yep, you can dash through the snow in a one-horse open sleigh that accommodates 6 passengers and comes complete with hot cider to be enjoyed around the fire in the barn at the end of your unique sleigh ride. For details and reservations, visit leavenworthsleighrides.com.

4. Knowing your cozy tiny house is waiting for you at the end of the day, a day trip to Seattle can be fun coming and going! In a little over two hours, you can be in the Emerald City and enjoy the attractions including the Space Needle, Pike Place Market, Winter Brilliance at the Chihuly Garden and Glass House, which has a special light and music installation running through February 2025. There’s also the Seattle Christmas Market, which runs through December 24, and has holiday displays, live entertainment and artisan shops to find that perfect holiday gift!

Leavenworth Tiny House Village
Leavenworth Tiny House Village

5. Toast the holidays in a variety of ways with a visit to Leavenworth’s Icicle Brewing Company’s taproom, located on Front Street in the downtown – drop in for Thursday Night Trivia or the special Holiday Market from 5-8 p.m. on Wednesday, December 11. If you want a wine toast, there are several tasting rooms on Front Street including Icicle Ridge Winery and the WooHoo Winery Tasting Room.

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