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About Jacksonville

Characterized by Victorian-style homes and picturesque forests and hills, Southern Vermont is truly a place where you can leave all your worries behind. Full of history, art, and culinary magic (think cheese), this region is comprised of small towns that offer up hospitality and charm in a scenic setting. Jacksonville is one such place. It's no wonder why Jacksonville was originally known as Point Pleasant, and our vacation rentals allow you to fully experience the refreshing nature of this beautiful area. 

Where is Jacksonville, VT?

A village in Whitingham, Jacksonville is home to only a few hundred people, making it the perfect spot to relax and rejuvenate amidst stunning New England beauty. Situated at the junction of Route 100 and Route 112, our vacation rentals are just north of the Massachusetts border near Green Mountain and Finger Lakes National Forest.

Things to Do in Jacksonville, VT

Vermont's lush landscape makes Jacksonville the ideal destination to get out and explore. Put on your tennis shoes, fill up your water bottle, and head to Molly Stark State Park, where you'll find a number easy hiking trails as well as Hogback Mountain Conservation Area (also known as the Marlboro Town Forest) adjacent to the park. Since 80 percent of Vermont is comprised of alluring forests, you'll have plenty of chances to work on your photography skills! 

Honora Winery & Vineyard has earned a five-star diamond distinction for its wines and breathtaking farmstead. Boasting 360-degree views of Vermont's Hogback and Haystack mountains, Monadnock Mountain in New Hampshire, and Mount Holyoke and the Berkshires in Massachusetts, this gorgeous 200-acre, family-owned estate farm will seemingly transport you from your charming vacation rental to Tuscany's wine country.

Nothing pairs better with wine than cheese, so it's a good thing Jacksonville is part of cheese country. The Spoonwood Cabin Creamery is a unique gem that serves up artisanal French-style semi-soft cheeses, which are hard to find in the United States. This family-owned creamery produces their cheese from organic and unpasteurized (60-day aging minimum) Jersey cows' milk. The shop even offers fresh goat cheese from spring through early fall.

Day Trips from Jacksonville, VT

Since Jacksonville is a village within historic Whitingham, you won't have to travel far to access some of the treasures of the city. Fall foliage is particularly stunning in these parts, and the Whitingham Village Historic District offers a useful history lesson about the city's prominent architecture. 

Snowy Stratton sits just 24 miles from Jacksonville. Stratton Mountain is a popular site in the winter especially, where skiers and snowboarders travel from all over the country to try their luck on the slopes. Summer offers ample opportunity for golf, tennis, and scenic hiking. 

Relaxation comes is many forms, but the small-town charm and gorgeous environment that Jacksonville offers are surely at the top of the list. Check out our vacation rentals today to experience an unbelievable getaway that you'll remember for years to come.