Windham Vacation Rentals

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About Windham

A town of roughly 500 residents, Windham is in many ways a classic Vermont destination – quaint, colonial, and far from city congestion. But what sets this tiny hamlet apart is its year-round outdoor activities and rich history going back all the way to the early 1800s. If you’re seeking small-town friendliness, pastoral views, and access to world-class outdoor recreation in the Green Mountains, look no further than our charming vacation rentals in this cozy New England burg. 

Where is Windham, VT?

Located in Southern Vermont, Windham lies about 10 miles east of the Green Mountains, with hiking, Nordic and downhill skiing, fly fishing, kayaking, and numerous other activities just a short drive west. Only 18 miles south of historic Ludlow and 17 miles east of outdoor-friendly Winhall, the area is especially popular with tourists from the neighboring states of New York and Massachusetts, who come for quick access to some of New England’s best downhill skiing at the nearby ski resorts of Magic Mountain Ski Resort, Bromley Mountain Ski Resort, Stratton Mountain Resort, and Mount Snow.

Things to Do in Windham, VT

With Windham’s close proximity to the Green Mountain National Forest, you can enjoy numerous activities in the great outdoors throughout the seasons! Warm weather visitors can take advantage of hiking, horseback riding, and mountain biking on 900 miles of multi-use trails, fishing in dozens of ponds, lakes, and rivers, and rock climbing on granite cliffs in the Green Mountains. In the fall and winter, abundant snowfall turns the trails to cross-country ski track while the nearby slopes come alive with downhill skiing and snowboarding.

If you’re a snow sports enthusiast, make sure to check out the wintertime fun at Magic Mountain Ski Area, the nearest ski resort, which is about six miles northwest from Windham. Ride a lift to its 2,850-foot summit for rocketing down 195 ski trails, its longest even stretching over a mile-and-a-half! Not only known for skiing, Mount Snow, 23 miles southwest, offers plenty of all ages entertainment and family-friendly activities, including sleigh rides through the backcountry, dog-sledding adventures, tubing, snowshoeing, and more. With our vacation rentals so close, you'll have an easy time returning for a hot home-cooked meal!

Any time of the year, it's a great idea to bring along your camera for snapping pictures of the local wildlife, but spring and summer are your best bet for capturing shots of skittish coyotes, hard-at-work beavers, notoriously shy moose, and black bears emerging from their dens. Fall is the best time of the year for capturing incredible landscape shots, with sugar maple, beech, and yellow birch trees lighting up the town’s hilltops and valleys in vibrant shades of red, yellow, and orange.  

Windham Village Historic District

On a stay in one of our Windham vacation rentals, make sure to bone up on the rich local history just beyond your doors. Include a stop at the town center’s Windham Village Historic District, which encompasses colonial buildings that have largely gone unchanged since the early 1800s. Drive along Windham Hill Road between Harrington Road and Stone Bridge Road for views of 13 historic buildings, including the Congregational Church. A focal point of the village, this church was built in 1802 and remains a good example of Greek Revival architecture. An interesting fact is that all 12 of the other historic district buildings are still occupied to this day, while many in similar high hill villages were abandoned over a century ago for economic reasons.

Day Trips from Windham, VT

Between days spent exploring in town or carving down powder-laden slopes at any of the area’s ski resorts, you might take a worthwhile drive to other quaint towns with unique cultural attractions. Just 18 miles north, a visit to Ludlow makes a fun day trip for its historic sites, including the Black River Academy Museum and High Street.

Continue your history lesson at the Southern Vermont Natural History Museum 32 miles south in Guilford. Fun for the whole family, this museum features interactive exhibits, educational events, and even the northeast’s largest taxidermy collection of birds and mammals native to New England. 

For a bigger city feel and a variety of shopping, dining, and entertainment options, a visit to Rutland, Vermont’s third largest city, is definitely worth the 38-mile drive north. Pack some sturdy boots for a hike on 325 acres of woodland trails at Pine Hill Park, then explore such noted attractions as the iconic Norman Rockwell Museum, the Chaffee Art Center, and the Paramount Theatre.  

A gateway to the Green Mountains with history and small-town charm, Windham welcomes your next Southern Vermont getaway with friends or family. Whenever you visit, you’ll find charming vacation rentals for year-round fun in this lovely Vermont town!  

Discover Windham

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Photo Credit: Josh Krancer via Flickr