Travel | December 10, 2020 10:11 am

The 10 Best Destinations for a Winter Workcation in 2021

Need a change of scenery? Warmer weather? Better wifi? Consider the work vacation.

breckenridge
Breckenridge, Colorado
Lucas Ludwig/Unsplash

It’s been a weird and almost entirely stagnant year for travel for reasons that don’t require much in the way of explanation. Nevertheless, out of the fires of the pandemic hell, a new trend has been forged: the extended work vacation, or workcation.

To call these elongated stays a vacation doesn’t feel quite right. Noticeably absent are the long days of sightseeing and late nights of fine dining, bar hopping and meeting new people in a city you’ve never visited before. In their place, you’ll have plenty of time to shack up, lay low and get some work done — just somewhere that isn’t the same house or apartment where you’ve been marooned since March, and in most cases, for 30 days or more.

There are a lot of things to consider when booking a remote, extended stay, particularly in a place you’ve never visited — the most pertinent being exactly how rampant COVID-19 is at any given moment. But, also, is there decent wifi? Do they allow pets? Are there safe, socially distant activities to partake of? Is it warm?

With all that in mind, we went ahead and compiled a list of 10 great spots to consider putting down roots in the coming months, each of them conducive to an extended stay.

And an important disclaimer: This is neither a ploy to encourage or discourage you from traveling. As we embark on what appears to be a second wave of the virus, we understand that certain precautions must be taken to protect ourselves — physically, obviously, but also mentally and emotionally. For some, that may mean packing up and heading somewhere warmer for the winter months so as to best combat seasonal depression. For those preparing for another imminent lockdown, it may come down to the need for a change of scenery, or even just more space to spread out. What we do encourage is for those who are traveling to do so safely, which is why we’ve only included destinations that require facial coverings, whether at state or county level. And if you do plan on embarking on any kind of stay — extended or otherwise — wash your hands, wear a mask and be respectful of the locals.

Narrowsburg, New York
Narrowsburg, New York
Airbnb

Best for a Cozy, Winter-y Winter: Narrowsburg, New York


The Catskills are an easy and accessible destination for anyone coming by way of NYC who wants to go somewhere but doesn’t necessarily want to travel. Remote and quiet, the Catskills hamlet of Narrowsburg —  a little more than a two-hour drive from Manhattan — is home to a population of just over 400. Needless to say, you’ll have no issues socially distancing here. Positioned on the Delaware River and just on the other side of the Poconos, Narrowsburg checks all the boxes if you’re looking for the quintessential Upstate experience. Hike the Tusten Mountain trail or take the opportunity to shop small, local businesses in the area without having to navigate the hustle and bustle of holiday and post-holiday crowds. Also just a short drive from Bethel Woods, home to the original Woodstock, you’ll notice small tributes to the festival scattered both on your way in and out of town. It is worth mentioning that winters in Upstate New York are notoriously formidable, so pack accordingly — we’re talking snowsuits.

Where to stay: With a recently installed WFH office nook in the master bedroom, the Stardust Cottage would be an idyllic spot to take your Zoom calls and ride out the cold. Amenities include laundry, wifi and a full kitchen. Typically $158/night, you can save 20% at booking on any stay in excess of 7 days.

Los Lunas, New Mexico
Los Lunas, New Mexico
Airbnb

Best for Year-Round Outdoorspeople: Los Lunas, New Mexico


Los Lunas, New Mexico is located 20 miles south of Albuquerque — around a 30-minute drive — along the banks of the Rio Grande and just off historic Route 66. If you’re the type whose sanity coincides with access to the outdoors, New Mexico may be the perfect place to settle down for a month or two. It does cool down significantly in the winter — mid-50s to 60s is normal in Los Lunas — but stays dry, meaning you’ll still get ample time outdoors, if not a tan. Tie in the fact that New Mexico boasts some of the lowest COVID numbers in the west and suddenly it’s doubled in appeal. Hike the Manzano Mountain Trail in the Cibola National Forest, peruse the Los Lunas farmers’ market for locally grown produce and feast on authentic (takeout) Mexican cuisine. 

Where to stay: The Lux Mini Farm House is only a 20-minute drive from the Albuquerque International Sunport and — quite literally — on a farm. There’s an onsite restaurant (where they serve fare from said farm) and a Euro-inspired coffee house, which means you never have to leave the premises. Fully equipped with wifi, laundry, a full kitchen and a private patio that could soon double as your home office, it’s $70/night to stay, but 15% off for long(er) term renters.

Cuernavaca, Morelos, Mexico
Cuernavaca, Morelos, Mexico
Airbnb

Best for the Grounded Jetsetter: Cuernavaca, Morelos, Mexico


To say that Mexico has fared well in the wake of the virus would be factually inaccurate, and we’d be remiss to suggest you head to Cancún or Tulum anytime in the immediate future. However, Cuernavaca in Morelos — located roughly 50 miles south of Mexico City — boasts a relatively low number of confirmed COVID cases, and temperatures seldomly lower than 75 degrees throughout the winter months. You’ll find at least one palace (belonging to Spanish conqueror Hernán Cortés), a few Diego Rivera murals and all of the vegetation to remind you that, yes, after months and months of being grounded stateside, you are in Mexico. It’s the perfect place to hole up while dosing on another culture, if that’s something you’ve found yourself craving in 2020. It’s important to monitor the constantly changing international travel restrictions in this case, but being that no one is being inundated with tourists at the moment, it may prove the perfect time to pack up and go — so long as your stay doesn’t exceed six months, per immigration laws.

Where to stay: This vintage villa is in the old, residential neighborhood of Bellavista, with large homes and gardens that pay homage to old Cuernavaca. In addition to being pet friendly — in the event you’ve been dreaming of taking your dog to Mexico — it also has wifi, laundry, a full kitchen, private terrace and a (shared) pool, making it the workcation destination of our dreams. It’s a little more than an hour and a half away from the airport, but fortunately it’s extremely easy to catch an Uber out of Mexico City. Stay here for $99/night after the 15% long term stay discount.

Breckenridge, Colorado
Breckenridge, Colorado
Airbnb

Best for Aspiring Ski Bums: Breckenridge, Colorado


If you’re interested in heading to Colorado for a long period of time in the dead of winter, we have to assume it’s probably to ski or snowboard. In Breckenridge, you’re looking at temperatures in the low 30s until April, with frequent snowfalls to match. It’s about 90 minutes from Denver International Airport, so consider renting a vehicle (may we suggest it have four-wheel drive?) or boost a lift from Epic Mountain Express and stay in walking distance to both the slopes and the village. Ski any one of five peaks (almost 3,000 acres), grab a drink after work at the highest distillery in the world or go fat-tire biking through hundreds of miles of trails. You’ll enjoy Rocky Mountain panoramas from just about every vantage point, and be sure to invest in some serious cold-weather gear prior to your departure.

Where to stay: For $376/night, you can wake up to these stunning views in your own private condo, located right at the base of Peak 9. You can ski in and out, as well as enjoy the outdoor hot tub after a long day on the slopes — or work, rather. This one comes with laundry, wifi and a full kitchen, making it a top-tier candidate for a remote stay in the mountains.

Austin, Texas
Austin, Texas
Airbnb

Best for Cross-Country Business Travelers: Austin, Texas


Texas didn’t make the list because it’s the ideal place to go in an attempt to steer entirely clear of COVID; however, there are a decent number of people who are still needing to travel for business purposes, meaning a central location — like Austin — would best suit their needs. And while the point is to stay in, there are still plenty of safe outdoor activities you can partake in should you get a little stir crazy. Rent a kayak on Lady Bird Lake, explore nearby McKinney Falls State Park, take a self-guided tour of the famous city murals and regularly indulge in authentic Texas BBQ from the comfort of your temporary home. During the winter months, you can expect temperatures from the mid-60s to 70s during the day with drops into the 40s at night, so pack pieces that will easily layer. And as enticing as it may seem, put off the urge to travel to other neighboring cities and stick to Austin — remember, this is a staycation.

Where to stay: This charming, eclectic duplex is only around a 20-minute drive from Austin-Bergstrom International Airport, in a quiet, centrally located neighborhood. It’s got a beautiful outdoor patio space where you can work from during the day, and a wood fireplace inside for the cooler evenings. Equipped with both wifi and a full kitchen, it’s generally $127/night, but any booking in excess of seven days earns you a 9% discount.

San Juan, Puerto Rico
San Juan, Puerto Rico
Airbnb

Best for the Work-Hours Beachgoer: San Juan, Puerto Rico


If the beach falls at the top of your remote stay list of criteria, San Juan, Puerto Rico, could be an optimal location for you to hunker down. Round trip flights to PR are extremely inexpensive out of most major cities, and the San Juan airport is a quick Uber from just about anywhere you’d need to go within the city once you get there. Temperatures range from the mid-70s at night to mid-80s during the day all winter long, and when looking at numbers of confirmed COVID cases, PR falls in the bottom 25% percentile (compared to U.S. states). Take a self-guided walking tour through Old San Juan, support local restaurants (10/10 would recommend  Verde Mesa) and hit the beach in between meetings — or during meetings. You won’t encounter as many tourists as you would this time of year under other circumstances, but — whether it be by land or sea — make sure to social distance.

Where to stay: About a 10-minute drive from the San Juan airport, stay at your very own private retreat, just a short walking distance from the beach. Overlooking the lagoon, this place offers a view of the sunset everyday, in-unit laundry, a full kitchen and wifi. You can stay for $142/night.

Newport, Oregon
Newport, Oregon
Airbnb

Best for Quiet Coastal Living: Newport, Oregon


At the (metaphorical) intersection of New England and the West Coast, you’ll find Newport, Oregon, a quiet city on the Beaver State’s central coast. Check out Nye Beach or Beverly Beach State Park (the latter of which is a likely spot to catch a glimpse of migrating whales in the right season), peruse the historic bayfront or grab a growler to-go from the Rogue World Headquarters on Yaquina Bay. Temperatures sit in the lower 40s to 50s in the winter months with quite a bit of rain, which is pretty on par with what you’d expect of the Pacific Northwest. The closest airport is Eugene — a roughly two-hour drive or three-hour bus ride, the appreciable reason for the lack of corporate influence in Newport and, alas, flocks of tourists.

Where to stay: This cozy, seaside retreat is a little more than an hour and a half from Eugene Airport, but only a short walk from Nye Beach — “the Gem of the Oregon Coast.” Here you’ll have wifi, laundry, a full kitchen and a small private backyard with a firepit where you can enjoy a dram of your favorite Scotch after a long day of working from home. Usually $145/night, you’ll get 5% off on an extended stay at booking.

Phoenix, Arizona
Phoenix, Arizona
Airbnb

Best for the Vitamin-D Deficient: Phoenix, Arizona


Another location to consider for logistics surrounding travel is Phoenix, with the Phoenix Sky Harbor International Airport just outside of the central city and a quick Uber away. In Phoenix, you’ll enjoy temperatures from the high 60s to the mid-70s until April, when it’ll start to really heat up again. Get outside for some urban hiking (Camelback Mountain, McDowell Mountain Regional Park, Piestewa Peak), rent a car and head to the drive-ins (which the area has seen a resurgence of since the start of COVID) and order fresh produce from local farmers’ markets online. As it stands now, there’s no statewide order mandating masks, though in Maricopa County, where Phoenix is located, there is.

Where to stay: Book this tranquil Arcadia bungalow just 10 minutes away from the airport, for $101/night at the 10% weekly discounted price. Like its predecessors, it also has wifi, laundry and a kitchenette, along with a fully furnished private patio and a grill.

New Orleans, Lousiana
New Orleans, Lousiana
Airbnb

Best for City People Who Just Need a Warmer City: New Orleans, Louisiana


If you’re not in need of a beach, while simultaneously not in the market for a cold, COVID winter, head to New Orleans to ride out this next (maybe) lockdown. It usually hovers somewhere in the mid-to-high 60s throughout the winter months in NOLA, sometimes dropping into the 40s at night, though it stays relatively dry. If you’re stepping out, go relax on the banks of the Bayou St. John, take a (masked) stroll through the Garden District or pop into the French Quarter and grab a cocktail to-go to remind yourself of better times. Also may not be a bad time to hop on the Saints bandwagon, if that’s your schtick.

Where to stay: This modern Victorian with old charm encompasses all the things we love about the Big Easy. It’s in the quiet neighborhood of Bywater (around a 20-minute drive from Louis Armstrong New Orleans International Airport) and just downriver from the French Quarter, but a bit outside of all of the commotion. Here, for $202/night, you can enjoy wifi, laundry, a kitchen, private porch and a fenced-in backyard.

Deerfield Beach, Florida
Deerfield Beach, Florida
Airbnb

Best for the Florida Enthusiast: Deerfield Beach, Florida


If you’re looking for a way to enjoy the South Florida beaches without having to maneuver around the traditional South Florida beach crowd, consider Deerfield Beach — about a half-hour drive from Fort Lauderdale-Hollywood International — as a palatable alternative. Temperatures range anywhere from high 60s to mid-80s, and the surrounding area lends itself to a range of outdoor activities. Check out the Deerfield Beach Boardwalk or any one of the local parks (Deerfield Island, Quiet Waters, Sullivan) for your daily dose of fresh air, or pick up cable water skiing as your latest quarantine hobby. All local beaches are open to the public, though if you plan to go, we’d implore you to avoid peak times, like weekends. Florida is not currently requiring masks statewide, but Broward County — home to Deerfield Beach — is.

Where to stay: Live like a local right here — a 30-minute Uber from the airport, and walking distance of the pier, beach and several restaurants. For $142/night, there’s wifi, laundry, a full kitchen and pets are allowed. It’s got all the makings of a typical beach stay to ensure that your workcation feels moderately more vacation-esque.