How to Make Winter Travel Easier

1. Pack Lighter With Winter Clothing Rentals Delivered to Your Hotel

Packing for a winter vacation can feel like a logistical puzzle. Puffy jackets, snow pants, and insulated boots take up serious real estate in a suitcase — and cost a pretty penny if you live in a climate that doesn't require them.

Enter Kit Lender, a winter gear rental service that ships high-quality apparel and accessories directly to your hotel. Instead of investing in pricey gear and lugging it across the country, you can arrive to find everything from base layers to ski jackets waiting for you. When your stay is over, simply return the kit and fly home with a much lighter bag. Or fill that extra space with souvenirs!

Benchmark Resorts & Hotels launched a new collaboration with the gear service this month at select properties, so now you can book your hotel room and that must-have winter attire from brands like Patagonia, Obermeyer, Hot Chillys and more in one fell swoop (another hack to make that winter getaway even easier).

2. Prepare for Travel Delays—and Try to Beat Them

Winter weather can wreak havoc on flight schedules, so a little strategy can go a long way. Take it from a seasoned traveler: Book the first flight of the day. Early-morning departures are statistically less likely to be delayed, as later flights are often affected by a cascade of disruptions from earlier ones.

3. Take Advantage of Off-Peak Rates at Summer Destinations

Some of the best winter getaways are places you’d typically visit in July. While you might not be able to go sunning on the beach, you can score excellent off-season rates and avoid peak-season crowds.

Book a stay at The Colony Hotel in Kennebunkport, Maine, to enjoy wintry small-town charm and scenic coastal walks — just bundle up before you head outside. Meanwhile, Wayfinder Newport in Rhode Island offers a cozy base for exploring Newport’s famed mansions, which are especially charming when decked out in seasonal décor.

4. Tap the Skills of a Ski Butler

If you’re heading for the slopes, let someone else handle the logistics. At The Equinox Golf Resort & Spa in Manchester, Vermont, Ski Butlers are on-hand to deliver your rental gear right to your room, organize reserved lift tickets and shuttle arrangements, and share insider tips for the best trails and après-ski experiences. With the details dialed in, all you have to do is enjoy your runs — and maybe reward yourself with a fireside cocktail afterward.

5. Choose a Resort With Plenty of Indoor Activities — Or Heated Outdoor Ones

Sometimes winter weather can take a turn for the worse, but that doesn’t mean your vacation has to stall. Stay at a resort with plenty of indoor activities, so you don't have to miss a day of fun.

At OKANA Resort & Indoor Waterpark in Oklahoma City, a full indoor waterpark means the whole family can splash around all day long, no matter the weather. In Utah's Heber Valley, Black Rock Mountain Resort offers an indoor game room with billiards and shuffleboard, as well as a new wellness club ideal for relaxing spa days. It also has a heated outdoor pool for those willing to brave the elements!

6. Stay In and Embrace Winter Coziness

Winter travel is about embracing the season, not rushing through it. Build in at least one slow morning or relaxing afternoon to savor your surroundings — and that's made all the better with an in-room soaking tub or a crackling fireplace.

Willows Lodge in Woodinville, Washington, has various accommodations with fireplaces for an ultra-cozy stay. At Skamania Lodge in the Columbia River Gorge in Washington, rooms invite you to enjoy winter indoors, whether you’re sipping hot cocoa by the fire or enjoying a warm bath in a soaking tub - or book a Treehouse with peaceful woodland views for an especially memorable trip.

Explore more destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.