The Best Over-the-Top Winter VRBOs

By Kaitlyn McInnis

Published

02/07/2023

The winter months can be tough: The days are shorter and darker, the temps can be downright bone-chilling, and the memories of warm summer months feel like they couldn’t be further in the rearview mirror.

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Whether the anecdote to the winter blahs is a winter wonderland or a balmy beach, we’ve rounded up a handful of VRBOs for chasing anyway whatever ails you. These over-the-top vacation homes range from $100+ a night to well over $10,000+ a night – so there are both bargains and splurges to dream about!

Cold Weather Destinations

Northwood Chalet Whistler

Whistler is of course home to the Blackcomb Ski Resort—one of the largest ski resorts in North America—so it only makes sense that the ski town just outside of Vancouver would make for an ideal wintertime getaway for snowsport fiends. The Northwood Chalet Whistler in particular was made for an over-the-top winter getaway thanks to the stunning A-frame design and uninterrupted views of the snow-covered mountain ranges and stunning Canadian wilderness.

Mt. Snow Area Private Estate

This private ten-bedroom vacation home in the mountains of Southern Vermont looks as if it was pulled straight out of Architectural Digest. It includes multiple saunas and hot tubs, a crackling fireplace, and it sits on several miles of private trails for hiking and snowshoeing without the crowds.

The Hygge Mountain

The Quebecois countryside in Canada is another one of those fairytale destinations that’ll serve as a reminder why the winter months can be so special. The Hygge Mountain is architecturally stunning and totally unique with floor-to-ceiling windows made for taking in the great outdoors while cozying up inside. The property also includes ski privileges at Stoneham Mountain Resort.

True Ski-in Ski-out at Big Sky Resort

This stunning ski resort in Montana is just about as close as you can get to sleeping on the slopes. The true ski-in ski-out property is conveniently tucked at the base of Big Sky Resort’s Whitewing run—giving skiers and snowboarders front-row access to all of the action. The huge vacation home is equally well-positioned for all things après-ski, including a massive fireplace and floor-to-ceiling windows that showcase wide-open mountain views.

Park City Cabin Retreat

This spacious escape in Park City was made to host family getaways—without anyone getting on each others’ nerves. It features four large bedrooms and three bathrooms, twenty-foot cathedral ceilings, a ton of natural light and views of the Wasatch mountain range from each window. There is also backcountry skiing, mountain biking, snowshoeing and hiking trails two minutes outside the front door and the Park City Ski resort is minutes away as well.

Exclusive Architectural Chalet in Switzerland

Who doesn’t want to spend some winter time in Switzerland? The Swiss Alps, warm cheese, endless chocolate… the Swiss really know how to make the most of warming up and getting cozy throughout the winter months. The Exclusive Architectural Chalet takes it all one step further: the stunning display of architectural ingenuity by the famed architectural firm Anako Architecture is perched on the side of the mountains, offering unobstructed views of the mountain ranges below. Interestingly, it also houses a museum-worthy collection of taxidermy animals on the top floor.

Warm Weather Destinations

Daphne By Luxury Villas Skiathos

You’re really paying for the sweeping views of the Aegean Sea when you book this vacation property—the home is just a bonus! The Daphne By Luxury Villas Skiathos is set on a cliffside cape in Skiathos, Greece with a sprawling terrace that provides dream-worthy and sun-soaked panoramas. It also includes an incredible infinity pool overlooking the sea below.

Luxury Oceanfront Villa

Set on the pristine coastline of Harbour Island in the Bahamas, this luxury oceanfront villa is the vision of over-the-top luxury—and the perfect winter escape. The nine-bedroom vacation home can comfortably accommodate up to eighteen people while the proximity to the ocean and world-famous Pink Sands Beach means you’ll be able to hit the beach every single day.

Gorgeous Poipu Beachfront Villa

Described as an “irresistible fusion of glamorous” this stunning Hawaiian getaway is the only single-family vacation rental on Poipu Beach. The backyard features its own gardens, spa, and generous-sized swimming pool—but don’t worry. There are also pristine white sand beaches just beyond the garden gates.

Ocean Front Punta Ballena Villa

In case you couldn’t tell, we’re a sucker for a good view, and this oceanfront property in Punta Ballena, Uruguay ticks off all the right boxes and then some. The five-bedroom villa sits atop a private resort overlooking the ocean. It’s ideal for boat-watching on the terrace and hanging out by the pool—but there’s also a tennis court and fully outfitted gym for working up a sweat.

Casa Azul Profundo

If you’ve always wanted to book a blow-out beach vacation for up to 32 of your closest friends and family then look no further than Casa Azul Profundo in Puerto Vallarta, Mexico. This oceanfront property is perched on a cliffside with spectacular views of the ocean below. The multi-level indoor/outdoor design makes it easy to let the fresh air inside but we suspect you’ll be spending most of the time by the infinity pool.

Oceanfront Home in North Myrtle Beach

If you’re short on travel time but don’t want to skimp on a stunning oceanfront getaway—look no further than this new oceanfront home in North Myrtle Beach. The sprawling property is set right on the water and features a private pool and spa area, a movie theatre, and a covered patio perfect for taking in the sunset views with loved ones.