Brattleboro Vacation Packages

With antique shopping, beer tasting, ski jumping and art browsing, this New England village is as diverse at its surrounding scenery.

Nestled against Green Mountain National Forest, Brattleboro is one of southern Vermont’s most picturesque villages. The quaint historic downtown has art galleries, boutiques, souvenir shops and antique stores. Stay in a downtown bed-and-breakfast to enjoy a picturesque setting and central location. 

After exploring, quench your thirst at McNeill’s Brewery, a beloved Brattleboro institution. Don’t let its unassuming facade fool you; the pub produces internationally award-winning beer. Latchis Theatre is known for its art deco architecture and historic setting: Watching a movie there feels like a journey back in time. Enjoy a live performance at Brattleboro Music Center, which provides monthly classical compositions. 

Brattleboro Museum and Art Center features local and international artists. The facility also premieres art-house films and offers live performances. On the first Friday of every month, artisans, musicians, and craftsmen show off their works at the Gallery Walk.

Sample the best local dairy products and watch cows take over Main Street each June during Strolling of the Heifers. Other festivals include the February Brattleboro Winter Carnival and the annual Film Festival, which premieres independent films from around the world. 

Surrounded by forests, Brattleboro is ideal for experiencing New England’s famous fall foliage. Stroll along Retreat Trails to see the landscape. If you’re feeling ambitious, hike to the summit of Mount Wantastiquet for panoramic views of Brattleboro and the surrounding region.

During the winter, watch daredevils get their adrenaline pumping at Harris Hill Ski Jump. Brattleboro is less than an hour’s drive from six ski mountains: Okemo, Magic Mountain, Bromley, Stratton, Ascutney, and Snow. You can also go skating or ice fishing on West River.

Brattleboro’s bus system offers comprehensive service throughout the town and the Amtrak station offers daily trains to and from major East Coast cities. Albany Airport is about 80 miles (130 kilometers) west of Brattleboro and Boston 112 miles (180 kilometers) east. 

Visit Brattleboro, the oldest town in Vermont, and many would say, the best!

Accommodation in Brattleboro

Pre-booking the perfect place to stay is imperative for a truly care-free vacation. You can find some of the best Brattleboro accommodation options on Expedia's easy-to-use lodging guide.

Top picks in Brattleboro include the 1868 Crosby House, which can be found at 175 Western Avenue, and Holiday Inn Express Hotel & Suites Brattleboro, located at 100 Chickering Drive. Alternatively, The Hampton Inn Brattleboro, at 1378 Putney Road, and the Latchis Hotel, at 50 Main Street, are a couple of offerings worth looking into if you're traveling on a budget.

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