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7 Best Northeast Winter Getaways for 2021

by Will Huck
best northeast winter getaways

Imagine you wake up on a beautiful winter morning, well-rested and eager to start the day. But something’s different. Why, you wonder? Because this winter morning you’ve woken up somewhere new. All the details—food, sleeping arrangements, activities—have been taken care of by the gracious hosts at your resort, hotel or B&B. All you have to do is throw on your favorite ugly sweater and enjoy the holiday. It sounds like a dream, I know, but this vision can be your reality. Whether it’s an all-inclusive resort in the Berkshires, a hotel at the center of a lively town or a mountainside B&B, these are the best Northeast winter getaways for 2021.

1. Woodstock Inn – Woodstock, VT

Situated in one of the prettiest Christmas towns in the Northeast, experience the holiday like never before at the Woodstock Inn. Historic homes are decorated to the nines with lights and Christmas ornaments, and horse-drawn carriages line the streets. As the special day approaches, enjoy various musical performances by choirs and orchestras, as well as countless holiday-themed activities in the streets. Furthermore, feel free to spend an afternoon at one of the many nearby ski areas.

The Inn itself offers cozy yet tasteful accommodations for its guests. Stay in the charming  Woodstock guest rooms, the decadent Legacy suites, or the Tavern rooms equipped with reading nooks and other structural quirks. As for culinary experiences, the Woodstock Inn has five restaurants, including the Red Rooster, known for its exquisite Christmas Feast. Plus, Richardson’s Tavern offers its regular dinner menu with Christmas Specials during the holiday season. Also, don’t forget to unwind at the spa—holidays are for relaxing, after all.

2. The Nantucket Hotel & Resort – Nantucket, MA

It may be known as a summer getaway, but Nantucket is the ultimate vacation spot year-round. Like many tourist towns in the Northeast, the island goes all out for the holidays. Downtown is completely decked out in Christmas decorations, which makes perusing its shops and restaurants double the fun.

As for your stay, prepare for a carefree, luxury getaway by the Nantucket Sound. From your suite at the Nantucket Hotel & Resort, you’ll be able to overlook the water as you sip your coffee or cocoa on Christmas morning. Curated and prepared by Executive Chef Al Cannito, the resort will also offer a first-class Christmas menu if you visit before the end of the year. This includes “Santa’s Brunch,” as well as a spectacular dinner that’s a staple on the Island. To top it off, the resort will also provide complimentary ferry rides on and off the island.

3. Kimpton Taconic – Manchester, VT

Buried deep in the picturesque mountains of Vermont, the Kimpton Taconic is a boutique hotel perfect for a holiday retreat. Whether you choose to stay in a guest room, suite or cottage, the accommodations are spectacular and full of yuletide spirit. Guests can expect tastefully curated artwork and a view of the surrounding mountainside (hopefully covered in snow). Best of all, the Kimpton Taconic is pet-friendly with no additional fees, so your furry friends can come along for the holiday.

While at the resort, patrons can unwind at the spa, peruse an exclusive boutique or enjoy a lavish meal at the Copper Grouse. Nearby, you can stroll through downtown Manchester to embrace the town’s immaculate decorations. Plus, there are plenty of activities away from the hotel to satisfy the adventurous spirit. Test your off-road driving skills at the Land Rover Experience or grab your skis and hit the slopes on Stratton Mountain. While Manchester is one of the most iconic destinations for autumn, it’s equally as sought-out in the winter.

4. Twin Farms – Barnard, VT

Best Northeast Winter Getaways for 2021

Photo via Twin Farms

Just south of Burlington, there’s a resort called Twin Farms—with 300 sprawling acres of bucolic serenity. It was once the personal estate of Nobel Prize-winning novelist Sinclair Lewis, where he and his wife often hosted notable political figures and literary experts throughout the 1940s and ‘50s. Today, Twin Farms remains a one-of-a-kind resort, where guests can experience the beauty of winter in Vermont.

The five-star accommodations and amenities at Twin Farms are second to none. Visitors have their pick of 20 unique cottages and various suites that are perfect for an intimate Christmas morning with the their significant other. As for activities, relaxation and luxury are on offer—this means seasonal farm-to-table meals, fine wine pairings and spa days. If you’re looking to roam off-campus, you can visit the Marsh-Billings-Rockefeller National Historical Park, tour a working farm or head up to the Killington Ski Area for a day on the mountain. Twin Farms is without a doubt one of the best Northeast winter getaways.

5. The Sagamore – Bolton Landing, NY

Founded in the 1880s, this sprawling resort has provided a charming winter escape for well over a century. Its marvelous location—an island on Lake George—makes it one of the most unique holiday retreats in the area. Whether you’re in the Historic Hotel or a lakeside condominium, guests will be ensconced by the scenic landscape of the Adirondacks that surrounds the lake.

The Sagamore has a vast selection of restaurants on-site for holiday-inspired meals to bring the family together, as well as exquisite brunch and dinner menus for Christmas day. Fine dining options include authentic Italian cuisine at La Bella Vita Italian Restaurant and a genuine New York Steakhouse experience at The Club Grill. Although it’s easy to get lost in the food at The Sagamore, don’t forget to make the most of its other amenities. The Sagamore takes pride in creating a whimsical winter experience, ripe with decorations and family-friendly activities.

6. Crystal Springs – Hamburg, NJ

Located in Sussex County, Crystal Springs Resort is one of the most iconic winter escapes in New Jersey. If you examine it by the numbers, it might just be the Northeast’s most expansive resort as well. Not only does it offer two sprawling hotels—Grand Cascades Lodge and Minerals Hotel—but it’s also home to two spas, three pool complexes and 11 eateries (which includes a wine cellar and a beer garden).

At Crystal Springs, the holiday experience includes delicious food and a spectrum of activities, including Winter Wonderland, Winter Workshop and more. Furthermore, between the resort and its surrounding landscape, the activities are endless. Visitors can explore a vast array of wineries and distilleries, peruse the many shops in nearby Warwick or check out the Emmerich Tree Farm.

7. The Inn Downtown – Portsmouth, NH

If you’re dreaming of a white Christmas, your best bet is heading up to Portsmouth, NH. Known as one of the best Christmas towns in the Northeast, Portsmouth is the ultimate holiday vacation spot. Visit the Music Hall for holiday performances, ice skate on Puddle Duck Pond and go on special candlelight tours of historic homes and museums. Plus, the decorations throughout downtown Portsmouth are said to be some of the best in the area.

The Inn Downtown places you in the heart of this festive city, while making you feel comfortable and at home. Given its central location in Portsmouth, guests are just a walk away from countless shops, restaurants and activities. It also provides a nice alternative to the many Victorian-style bed and breakfasts that seem to have overrun the Northeast. Visitors can choose from 10 studio apartments in the building, each of which offers a kitchen and modern decor.

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