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Great Winter Vacation Rentals Under $100 a Night — If You Share

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Splitting the Bill

November through February are opportune months for winter sports, as snowfall accumulates on the slopes offering up opportunities for skiing, snowshoeing, snowmobiling, sledding, and more. Whether in California's Olympic Valley, Colorado's ski towns, or New England's snowy charm, cheap homestays can be found for nightly rates of less than $100 a person. So grab the extended family or those trusted folks in your pandemic bubble and plan a winter wonderland getaway.

Related: 20 Best Winter Home Rentals in America

Super Ski Pad
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Super Ski Pad

Breckenridge, Colorado |Sleeps 4
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Colorado boasts some of the nation's best ski slopes, especially Breckenridge. This one-bedroom condo is located near almost everything, including historic Main Street and the Breckenridge gondola.

vacation rental in Girdwood, Anchorage, Alaska
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Kenai Peninsula Condo

Girdwood, Alaska | Sleeps 6
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For those heading to Mount Alyeska for the vast snowfall, this two-bedroom, two-bath condo has a newly remodeled kitchen and bathrooms, along with plenty of amenities. The condo is close to several great restaurants, as noted by the owner, as well as the Alyeska Resort chairlifts.

Related: 15 Best Places to See the Northern Lights on a Budget

Mountain View Condominium
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Mountain View Condominium

Whistler, British Columbia | Sleeps 4
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Canada is home to miles of slopes and plentiful snowfall — and the largest ski resort in North America, Whistler Blackcomb. For less than $40 a night per person, this studio suite is a steal. The area of White Gold, located close to the town center, boasts amazing mountain backdrops. Guests have access to an outdoor hot tub.

Mountain View Home
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Mountain View Home

Warren, Vermont | Sleeps 10
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This eclectic four-bedroom, two-bath rental allows for a couple of families to stay for a very reasonable nightly rate. It's less than a mile from Sugarbush Ski Resort, and amenities include a fireplace, WiFi, TV, and "the cozy ambience of a mountain tree house."

Related: The Prettiest Floating Cabins Around the World

Remodeled Mountain Condo
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Remodeled Mountain Condo

Silverthorne, Colorado | Sleeps 4
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This remodeled Summit County ski condo is perfect for a group that includes a couple or two. Get comfortable with two bathrooms and a balcony with incredible Rocky Mountain views. Hit the slopes at nearby Keystone, Arapahoe Basin, Copper Mountain, or Breckenridge, and unwind at night by the fireplace or clubhouse swimming pool.

Secluded Connecticut Charm
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Secluded Connecticut Charm

Sharon, Connecticut | Sleeps 8
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Come home from your days on the Mohawk Mountain Ski Area slopes to this spacious, 2,500-square-foot barn-converted home. Located on 70 acres of private woodland, amenities include a game room, wood-burning fireplace, and hot tub. 

Related: 10 Prefab Cabins That Can Be Shipped to Your Door

Taos Ski Village Condo
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Taos Ski Village Condo

Taos County, New Mexico | Sleeps 4
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This adorable and light-filled one-bedroom, one-bath condominium is within walking distance of the ski lifts and about eight miles from Red River Ski Area. Need a day off from skiing? It's less than 15 miles from the historic Taos Plaza, too.

Main Street Digs
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Main Street Digs

Park City, Utah | Sleeps 5
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This 1,200-square-foot condo puts renters in close proximity to ski or board nearby Park City Mountain or Deer Valley resorts. Not a skier? No problem. You're just steps from Main Street's restaurants, saloons, pubs, museums, and more. 

Related: 50 Best Small Towns to Visit in Winter

Quaint and Cozy Townhome
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Quaint and Cozy Townhome

Olympic Valley, California | Sleeps 6
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Less than two miles from the Village at Squaw Valley, this two-bedroom, two-bath condo offers plenty of space for three couples or a family with 1,634 square feet. Amenities include a fireplace and washer and dryer. 

Ski-In/Ski-Out A-Frame Duplex
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Ski-In/Ski-Out A-Frame Duplex

Snoqualmie Pass, Washington | Sleeps 10
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With this pet-friendly rental you'll be just steps away from alpine skiing and snowboarding, Nordic skiing, and winter tubing. After a long day on the slopes, warm up in front of the fireplace, play games, or enjoy a warm winter cocktail on the deck. 

Related: A-Frame Cabins That Are Perfect for Fall Getaways

Family-Friendly Condo
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Family-Friendly Condo

Sun Valley, Idaho | Sleeps 7
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Sure, you might be pretty cozy with seven others in this 623-square-foot space, but who really cares when you're spending your days on the slopes of nearby Sun Valley Ski Resort? When you are at the condo, you can relax in front of the gas fireplace, refuel in the fully equipped kitchen, or take in the views from the large deck.

Mountain Cabin
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Mountain Cabin

Nederland, Colorado | Sleeps 6
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Get the best of all worlds with this nearly 1,300-square-foot, two-bedroom, one-bath cabin. Eldora Ski Resort is only 10 minutes away, there are cross-country ski trails right outside the cabin door, and the towns of Nederland and Boulder are a short drive away. Amenities for this pet-friendly rental include a fireplace, washer and dryer, TV, and internet. 

Related: 13 Destinations for Cheap Skiing in 2020

A-Frame Ski Chalet
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A-Frame Ski Chalet

Harbor Springs, Michigan | Sleeps 8
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If you enjoy minimalism and mid-century modern design, you'll love this two-bedroom, two-bath rental that's within walking distance of the state's Nub's Nob Ski Area. Want a day off from rolling in the snow? Both Harbor Springs and Petoskey are a few minutes drive away and offer lots of shopping and dining opportunities. 

Luxe Big Sky Condo
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Luxe Big Sky Condo

Big Sky, Montana | Sleeps 6
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Stay in style in this remodeled two-bedroom, two-bath condo with an open floor plan, gas fireplace, laundry facilities, hot tub, and more. Catch a shuttle right outside the building to the slopes, or drive less than a mile to shopping, restaurants, ice skating, and more. 

Related:  25 Coolest Tiny Home Rentals on Airbnb and VRBO

Sugarloaf Ski Cottage
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Sugarloaf Ski Cottage

Stratton, Maine | Sleeps 7
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This pet-friendly, 2,200-square-foot rental provides stellar views of Mount Bigelow and the Sugarloaf Ski and Golf Resort, which is just over 10 miles away. If you're a fan of less adrenaline-inducing ski adventure, there are cross country trails right outside the door. Amenities in this cozy and eclectic space include a wood-burning stove and an open floor plan. 

Related: 25 Vacation Rentals with Secret Rooms and Hidden Passages