Home Lifestyle 10 Unique Winter Getaways Within 2 Hours of Hoboken + Jersey City

10 Unique Winter Getaways Within 2 Hours of Hoboken + Jersey City

by Stephanie Vermillion
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Now that winter is in full swing, there’s no better time to get the heck out of Dodge (ehh, Hudson County). Although a tropical trip to Cancún, the Bahamas, or San Juan may be out of the budget + too far to travel, New York, New Jersey, and Connecticut have a variety of winter getaways that make the season not just manageable, but fun, even in the snow. If you’re in need of a quick winter trip, check out these amazing weekend getaway destinations within two hours of Hoboken and Jersey City.

Tiny House Resort | South Cairo, NY

tiny house think big

This picture-perfect collection of adorable cabins is located in the woods of South Cairo. Tiny House Resort guests have a variety of cozy cabins to choose from, including The Green Bean, a quaint little dog-friendly cabin with massive windows, a hot tub, and even a private entrance to the dog park. Another great option is The Oki, as it offers guests impeccable views from a 13-foot glass window with a snug, lofted bed above the living room.

Skytop Lodge | Skytop, PA

Skytop Lodge

(Photo credit: @skytoplodge)

This historic Skytop Lodge has been welcoming guests to its magnificent, regal grounds since 1928. The 5,500-acre resort is located on the Poconos’ West Mountain, making it a great destination to ski or tube during the day, with a Skyview Spa massage or Library Lounge drink waiting for guests in the evening. While the outdoor activities are a big draw, there are plenty of indoor activities to keep cozy, including ax-throwing, an indoor pool, and paddle tennis.

Read More: Catskills Getaway: A Weekend at the Tiny House Resort

The Kaatskill Mountain Club Lodge | Hunter, NY

The Kaatskill Mountain Club Lodge

(Photo credit: @huntermountain)

Located on the slopes of Hunter Mountain, the Kaatskill Mountain Club Lodge offers ski-in, ski-out rooms as well as a four-season heated pool to help guests enjoy their charming Catskills surroundings. The upscale lodge was built with skiers and snowboarders in mind, as it offers ski and snowboard storage, as well as steam rooms, saunas, and outdoor hot tubs for relaxing after a vigorous day on the slopes. While the main draw in the upper Catskills is skiing and other outdoor activities, there are plenty of other activities to enjoy such as art galleries and historical sites.

Mayflower Inn | Washington, CT

mayflower inn

(Photo credit: of Mayflower Inn)

With 58 acres of woodland and gardens, not to mention a fireplace and sunroom,  the Mayflower Inn is a must-stay spot for those visiting Connecticut’s charming town of Washington. The village itself is filled with quintessential New England charm, including colonial buildings, horse-drawn carriages, local vineyards, taverns, and restaurants, most within a half-mile walk from the Mayflower. The Inn is a destination in itself and has several ‘artists in residence’ of different media throughout the year. Depending on the timing, it may be a chef, or a painter, or even a poet. Guests can interact with the artist and their work is on display.

Crystal Springs Resort | Hamburg, NJ

crystal springs resort nj

(Photo via @crystalspringsresort)

The massive, luxurious Crystal Springs Resort is a destination within itself. The resort offers guests a variety of activities including upscale dining, the Elements Spa, an on-site wine cellar, and quick access to the neighboring Mountain Creek ski slopes. Make sure to check out the resort’s calendar of events, as their weekend lineups range from marshmallow roasts to canvas painting.

The Palms Hotel | Fire Island, NY

palms hotel fire island

Photo via @palmshotelfireisland

(Photo credit: @palmshotelfireisland)

While Fire Island draws tourists all summer, it’s equally enjoyable — and much less crowded —in the winter. The boutique, seaside Palms Hotel is a great place to stay for access to the beaches, which are known to have deer, owls, and even seals during the quieter winter months. The hotel has traditional rooms and suites as well as cottages and bungalows for bigger groups. 

Mohonk Mountain House | New Paltz, NY

mohonk mountain house getaway

(Photo credit: @mohonkmountainhouse)

Founded in 1869, Mohonk Mountain House is a majestic winter getaway overlooking the Hudson Valley. The Victorian Castle Resort is both historic and charming, with wrap-around porches, an indoor pool, and upscale dining. Visit for the nearby skiing, snowboarding, or skating, but stay for the serene, award-winning spa.

Shorecrest Bed + Breakfast | North Fork, NY

(Photo credit: Shorecrest Bed + Breakfast)

Tucked away on a quiet stretch of the North Fork shoreline, the charming Shorecrest Bed + Breakfast makes guests feel right at home. Whether it’s the proximity to nearby vineyards like One Woman Wines or the B+B’s homemade breakfast served in a formal 1860s dining room, this quaint little inn is a perfect place to unwind and relax in Long Island’s quiet North Fork. Parts of the property are pet-friendly, so even Fido can get a vacation as well.

See More: Winter Weekend Getaway to Hunter Mountain Ski Resort

YO1 Wellness Center | Monticello, NY

(Photo credit: @yo1catskills)

YO1 Wellness Center, located in Monticello, New York (about two hours by car from NYC) is a luxury, state-of-the-art retreat that aims to enlighten its guests “about the essence of eternal youth and consciousness,” with luxe treatments and an expansive property (that is housed on the old Kutscher Resort). It’s the first luxury nature cure destination of its kind in America, created to awaken the body’s ability to self-heal. YO1 provides individual wellness programs for guests, customized to yield results through the ancient Indian therapies of Naturopathy, Ayurveda, and Yoga. Each immersive, customized, and all-inclusive stay is designed to help find a balance between mind, body, and soul, and to reshape and transform the patterns of daily lifestyle. It’s truly the ultimate retreat to just get away, reboot, and recharge.

Woodstock Way | Woodstock, NY

woodstock way ny hotel

A Hoboken Girl favorite (may remember our office team retreat here a few years back), this getaway is a breath of fresh air just an hour and 45 minutes from the Hudson County area. The ultimate glamping experience: Think waking up to woods and waterfalls outside your room, floor-to-ceiling windows, heated bathroom floors, and lush Brooklinen sheets. Plus a town right outside your doorstep to explore, filled with charming shops and eateries.


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