Winter Travel, Simplified

We've teamed up with Kit Lender to help you get all the cold weather gear you need to adventure. Spend less time worrying about lugging bulky gear or airport baggage restrictions—and more time immersing yourself in curated local experiences.

Winter Travel, Simplified

We've teamed up with Kit Lender to help you get all the cold weather gear you need to adventure. Spend less time worrying about lugging bulky gear or airport baggage restrictions—and more time immersing yourself in curated local experiences.

How It Works:
Arrive, Gear Up, & Get Out There

By teaming up with Kit Lender, we've designed your one-stop-shop for winter trip planning. It's easy:

>Book your reservation from the hotel packages below.

>Benchmark's Adventure Concierge will connect you with Kit Lender to lock in your winter apparel needs, style preferences, and sizes.

>Arrive at your hotel, and your custom gear kit will be waiting!

>When it's time to head home, you'll leave your gear with the front desk—seamless and hassle-free.

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Kit Lender Resort Packages

Book a 4+ night stay and let us handle your gear—so you can save space in your suitcase and focus on your adventures. Kit Lender's winter apparel kits include premium gear from leading brands like Patagonia, Spyder, and Burton.

Expert Itineraries for Each Destination

You've got the fit—now get out there! Our local resort experts share all the intel on the must-do's in every destination. Click the + below to explore winter escapes in Colorado, Oregon, Utah, Vermont, and California.

  • South Lake Tahoe, California

    Itinerary crafted by Jerry Bindel, general manager at Forest Suites Resort, Tahoe enthusiast, and local legend

    Day 1

    • Arrive at Forest Suites Resort, just steps from the iconic Heavenly Village and Gondola. Your custom Kit Lender package will be waiting upon check-in, ensuring you are adventure-ready from the moment you arrive.
    • Start your vacation with a complimentary glass of wine at the resort’s weekly wine reception before heading out for dinner.
    • Check out some of Tahoe’s most sought-after dining experiences, like Hell’s Kitchen by multi-Michelin star chef and television personality Gordon Ramsay, or Wolf by Vanderpump.
    • End the day with live music and a nightcap at Noel’s Apothecary – a coffee shop by day, and speakeasy by night.

    Day 2

    • Before you head out for the day, fuel up at the resort’s complimentary hot breakfast buffet, served daily from 7 - 10 am.
    • Hit the slopes at Heavenly Mountain, where skiing and snowboarding are spread across 4,800 acres. Ride the Heavenly Gondola (located just steps from Forest Suites Resort) for a breathtaking 2.4-mile journey high above the lake. Halfway to the top, stop at the observation deck to take in panoramic views of South Lake Tahoe (also doubling as the perfect selfie backdrop).
    • As you make your way down the mountain, look for the trail markers that guide you to the Nevada state line for a chance to have your skis or snowboard in two states at once!
    • Take a break from the powder with lunch at East Peak Lodge, located right on the mountain. Enjoy delicious BBQ while dining outside, soaking up the sun, and vibing to beats by Rockstar DJ Cat.
    • After your day of adventure, soothe your tired muscles with a soak in one of Forest Suites' outdoor hot tubs.
    • Check out The Loft, located right next door in Heavenly Village. Start with tapas and cocktails by the indoor fire tables, then take your seat for a one-of-a-kind magic show packed with clever comedy, mind-bending illusions, and interactive moments that pull you right into the action.

    Day 3

    • Venture into the Sierra Nevada backcountry on an unforgettable guided snowmobile tour with Zephyr Cove Resort. This adventure takes you across 45 miles of rugged, snow-covered terrain, climbing to 9,000 feet for jaw-dropping lake views and wide-open alpine vistas.
    • Take your time exploring the Shops at Heavenly Village, home to everything from art galleries and cozy winter wear to one-of-a-kind Tahoe souvenirs—perfect for finding something special for everyone back home.
    • Hit the town tonight for an evening of fun! Kick off the night at McP’s Taphouse with hearty Irish dishes, 40 beers on tap, and live tunes from a local musician. Then make your way to Caesars Republic to try your luck at the poker table or slot machines in this sleek, newly renovated casino. Who knows, you might just hit the jackpot!
    • For late-night bites, swing by the Lucky Beaver, open 24/7, and dig into their famous, award-winning burgers.

    Day 4

    • Reconnect with nature on a guided Tahoe Snowshoe Tour, where scenic alpine trails lead to sweeping views of Lake Tahoe’s winter landscape—an invigorating way to experience the region’s quiet beauty.
    • Unwind with an afternoon massage from Saundra, Forest Suites’ in-house massage expert. Her personalized treatments ease sore muscles and leave you feeling fully restored after days of adventure.
    • Cap the day with a serene lakeside dinner at Riva Grill at Ski Run Marina, Tahoe’s premier waterfront dining destination. Savor expertly prepared steak and seafood paired with craft cocktails as the sun dips behind the mountains. Afterward, stroll along the beach for a moment of stargazing—an unforgettable finale to your Tahoe escape.

    Day 5

    • Pack up your Kit Lender gear in the provided box and deliver it to the front desk for return shipping – easy and hassle-free.

  • Bend, Oregon

    Itinerary crafted by Samantha Tullis, Bend native and meeting manager at Riverhouse Lodge.

    Day 1

    • Check in at Riverhouse Lodge, a rustic retreat on the banks of the Deschutes River. Your custom Kit Lender package will be waiting upon check-in, ensuring you’re adventure-ready from the moment you arrive.
    • After settling in, take the Deschutes River Trail directly behind the lodge for an easy winter walk, soak in scenes of snow-dusted pines, and shake off your day of travel.
    • Head to The Lot for a casual dinner. This popular food-truck pod features enclosed seating and heated benches, making it a cozy, winter-friendly spot just minutes from the resort.

    Day 2

    • Spend the day on the slopes of Mt. Bachelor, just a short drive from Bend. You’ll find world-class skiing and snowboarding for every skill level across the mountain’s more than 4,300 acres of terrain. Park at West Village Lodge for the most central access to the mountain, or head to Sunrise Lodge for the most beginner-friendly terrain on the mountain.
    • Break for lunch at Rock Bar, where you can warm up with comfort food and a hot toddy, with options to sit inside or outside.
    • Warm up back at the resort’s indoor heated swimming pool. Stick around for one of Riverhouse Lodge’s nightly dive-in movies – showtime is at 6 PM.
    • End the evening with a cozy dinner at Currents, the lodge’s signature restaurant, offering Pacific Northwest flavors and serene river views.

    Day 3

    • Set out for a dog sledding adventure led by professional mushers. You’ll be tucked warmly into the sled while you fly along snowy, tree-lined forest trails near the slopes of Mt. Bachelor.
    • Wander through downtown Bend’s boutique shops before an early dinner at Pine Tavern, Bar RBC, or Bos Taurus.
    • Cruise through the forest of Oregon’s Cascade Mountains on a snowshoe trek lit by headlamps. Your route leads you to a hand-carved amphitheater in the snow. Warm up at a bonfire while sipping hot cocoa infused with hazelnut espresso vodka, and enjoy treats from a local bakery.

    Day 4

    • Explore Newberry National Volcanic Monument on a guided tour with views of the Cascade Mountain Range, Benham Falls, and more. This 3-mile walking tour gets you up close with the region’s geology and cultural history. 
    • Enjoy lunch at Wild Rose or The Lemon Tree in downtown Bend before spending the afternoon on the Bend Ale Trail. Launched in 2010 as the first beer trail in the West, the Bend Ale Trail includes more than 30 breweries and tasting rooms in seven territories. Stop by the Bend Visitor Center for a free collectible passport.
    • Book a table for dinner at Bend’s Zydeco Kitchen & Cocktails, consistently recognized as one of Central Oregon’s best restaurants.

    Day 5

    • Grab a coffee at the resort’s lounge for a morning stroll along the Deschutes River. Then, enjoy a full breakfast at Currents.
    • Pack up your Kit Lender gear in the provided box and deliver it to the front desk for return shipping – easy and hassle-free.
  • Heber City, Utah

    Itinerary crafted by Jack Tamasi, director of front office at Black Rock Mountain Resort

    Day 1

    • Arrive at Black Rock Mountain Resort, your home base to explore Park City and Deer Valley. Your custom Kit Lender package will be waiting upon check-in, ensuring you’re adventure-ready from the moment you arrive.
    • Stroll Park City’s historic Main Street or lace up your skates for outdoor ice skating at Park City’s Resort Center Ice Skating Rink, located at the base of the majestic Park City Mountain Resort, just 20 minutes from the resort.

    Day 2

    • Travel 10 minutes to ski the world-famous slopes at Deer Valley and experience its historic East Village expansion with more than 10 new lifts, 100+ trails, and a new gondola. Want to hone your skills? Try Ski with a Champion and train with an Olympic athlete.
    • Enjoy apres-ski in a Deer Valley champagne yurt, where ski gear gets traded for champagne flutes and caviar, or head back to the Black Rock Mountain Resort for a cozy dinner at Overlook
    • Kick start your post-ski recovery at Black Rock Mountain Resort’s Onyx Club, a new two-story, 10,000-square-foot wellness center and social hub. Unwind in the sauna or steam room, recharge in the gym, or take a dip in the heated pool, all just steps from your suite.

    Day 3

    • Zip through Utah’s snowy backcountry mountains on a half-day snowmobiling experience with Woodland Snowmobiles. With a shuttle pick up and drop off available at Black Rock Mountain Resort, checking this adrenaline-pumping experience is easy.
    • Grab lunch at the resort and take an afternoon dip in the pool.
    • Bundle up for a horse-drawn sleigh ride through snow-capped mountains before having dinner at Park City’s Viking Yurt.
    • Warm up back at Black Rock Mountain Resort’s outdoor hot tub.

    Day 4

    • Spend the morning hiking on the North Round Valley Trailhead. This trailhead offers access to easy-to-moderate trails that are great for hikers of all skill levels.
    • Take a drive to Midway, a neighboring town with a rustic farm vibe. If you’re a chocolate lover, be sure to stop by Ritual Chocolate. This award-winning small batch, bean-to-bar chocolate has been named one of the best craft chocolate makers in the country by Smithsonian Magazine.
    • Make a stop at Hannah Neeleman’s Ballerina Farm, also in Midway, for a farm-to-basket market experience. Browse this shop to discover local artisan foods, pantry must-haves, and home and wellness goods.

    Day 5

    • See Park City in a new light on a sunrise snowshoe tour.
    • Warm up with breakfast on Park City’s Main Street before gliding across the snow-covered terrain on a dog sledding adventure.
    • Back at Black Rock Mountain Resort, pack up your Kit Lender gear in the provided box and deliver it to the front desk for return shipping – easy as that!
  • Manchester, Vermont

    Itinerary crafted by Erica Mulready, Manchester, Vermont local and lead resort reservationist

    Day 1

    • Arrive at The Equinox Golf Resort & Spa, the storied Manchester retreat that has welcomed presidents, dignitaries, and travelers for over 250 years. Your custom Kit Lender package will be waiting upon check-in, ensuring you’re adventure-ready from the moment you arrive.
    • Pick up your ski or snowboard gear directly at The Equinox so you can get a quick and easy start tomorrow. The Ski Butlers team will personally outfit you with skis, boots, poles, or a snowboard – right at the resort for seamless prep for the slopes.
    • Enjoy dinner at The Equinox’s Chop House and choose from a menu that features the finest chops, unique fish and seafood preparations, and a curated selection of wine and spirits. A must-try dish: the prime ribeye and honey ginger carrots.

    Day 2

    Day 3

    • Grab a sled from the resort’s front desk and zoom down the snowy hill just beyond The Equinox.
    • Bundle up and wander into downtown Manchester Village. Explore this quintessential New England town brimming with cozy shops, art galleries, and inviting restaurants.
    • Enjoy a casual dinner at The Equinox’s fabled Marsh Tavern – a favorite for Manchester locals and visitors since 1769 – before satisfying your sweet tooth with gooey s’mores by the outside firepit.

    Day 4

    • Start your morning with a quiet hike along the Equinox Preservation Trails to discover The Equinox Pond, waterfalls, creeks, and wildlife like deer, hares, and red foxes. Looking for a bigger adventure? Hop inside a Land Rover to learn expedition-style driving and off-roading techniques on an 80-acre course at The Land Rover Experience, located at the resort.
    • Book a table for dinner The Silver Fork, a top-rated dinner destination that offers a seasonal menu.
    • Check out Manchester’s Pastime Pinball for a nostalgic night out. This pinball museum and arcade has been open for more than 75 years and features over 60 vintage and modern games.

    Day 5

    • Get a slow start to your day with a morning yoga or Pilates class at The Equinox’s spa or team up with one of the resort’s personal trainers for a more intense sweat session.
    • Pack up your Kit Lender gear in the provided box and deliver it to the front desk for return shipping – easy and hassle-free.
    • As you head out of town, visit Hildene, The Lincoln Family Home, and explore the beautifully preserved estate set against the backdrop of the Green Mountains.

  • Vail, Colorado

    Itinerary crafted by Donna Randrianjohary, concierge at Tivoli Lodge

    Day 1

    • Welcome to Tivoli Lodge! Expect to be greeted by Racer, the lodge’s resident chocolate Labrador.
    • Settle into your room, drop your bags, and ease into the evening with a warm drink in the inviting lobby—an instant welcome to Vail’s alpine charm. Your custom Kit Lender package will be waiting upon check-in, ensuring you’re adventure-ready from the moment you arrive.
    • Step outside for a leisurely winter stroll through Vail Village, where gas-lit streets, cobblestone-style walkways, and crisp mountain air create a postcard-perfect setting.
    • Wander across the iconic covered bridge and follow Gore Creek, pausing to take in serene winter views and capture a few memorable photos along the way.
    • Enjoy dinner at Sweet Basil, a creative, modern American restaurant that features seasonal, imaginative cuisine with an innovative array of diverse influences.
    • End the evening with a peaceful walk back to the lodge beneath twinkling lights, as Vail Village glows softly under a blanket of snow—pure winter magic.

    Day 2

    • Start your day with the lodge’s American-style breakfast buffet before heading out to hit the slopes of Vail Mountain, with Gondola One just steps from Tivoli Lodge – perfect for early access to pristine, freshly groomed slopes.
    • Pause for a mid-morning coffee at Loaded Joes, located across from the Vail Village parking in Austria Haus, or ski through to lunch when you grab a table at Buffalo’s Roadhouse Grill. Warm up with comfort food like chili or bison stew and cornbread before heading back out for the afternoon.
    • Time to après ski! Walk to The Red Lion in the heart of Vail Village for live music, hot drinks, and classic Vail energy.
    • Relax in the lodge’s outdoor hot tub with snowy views before a casual dinner at Bully Ranch. Featuring a menu of Southwestern and American fare, this spot of a local favorite.

    Day 3

    • Take a guided snowshoe tour through Vail Nordic Center or Piney Lake wilderness area. These quiet forest trails will inspire you to slow down and fully take in the alpine surroundings. You’ll feel worlds away from the hustle and bustle of everyday life as you take in serene snow-covered landscapes, wildlife tracks etched into the powder, frozen lakes, and sweeping mountain views.
    • Refuel with lunch at Big Bear Bistro, then enjoy a tranquil winter walk along the Gore Creek Trail, easily accessed right from Vail Village.
    • Warm up back at Tivoli Lodge with cookies and hot chocolate, a cozy treat after a day outdoors.
    • Spend the evening on a horse-drawn sleigh ride and dinner at 4 Eagle Ranch, gliding through a snow-covered meadow before settling in for a rustic, fireside meal – one of Colorado’s most unforgettable winter experiences.

    Day 4

    • Head out for a thrilling snowmobile adventure with Nova Guides, climbing to the summit of Camp Hale at 12,500 feet, an awe-inspiring journey into Colorado’s high alpine backcountry.
    • Traverse expansive powder fields and wide-open alpine meadows, with sweeping Rocky Mountain views stretching for miles in every direction. Along the way, pause at scenic overlooks for photos, snow play, and a moment to fully take in the dramatic landscape.
    • Return to Vail in the afternoon and lace up your skates at the outdoor ice rink at Solaris Plaza. This quintessential activity is set in lively Vail village and makes for a classic winter moment. When you’re done, wander the snow-lined pathways of the village and do a bit of shopping.
    • Enjoy dinner at Vail Chophouse for great steaks, fresh seafood, and signature cocktails.

    Day 5

    • Savor your final morning in Vail with a warm cup of coffee by the lodge’s fireplace.
    • Before you go, simply pack up your Kit Lender gear in the provided box and leave it with the front desk for return shipping—effortless and completely hassle-free.