Discover a selection of 59 vacation rentals in Winchester that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $110 per night, and houses and condos are popular options for a stay in Winchester. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Winchester
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Destination guide

Discover a new favorite getaway in Winchester

Winchester is a quiet spot in Connecticut's Litchfield County, offering a family-friendly base for vacations in New England. Natural delights situated right in town – including Mad River and the Platt Hill State Park – place outdoor adventure on the doorstep. If you're a keen angler, aim to score one of the Winchester vacation rentals beside Highland Lake. The town's historic downtown, a lovely place to indulge in the local stores and dining spots, offers a somewhat slower pace of life, though if you're up to exploring a little further afield, you'll find the town just a short, scenic drive from the ample attractions of the Berkshires.

Things to do

New England appeal in Winchester

The pretty town green in Winchester Center paints a quintessential picture of New England. A cozy gazebo surrounded by plants is a lovely spot for coffee and conversation, while culture comes courtesy of nearby historic buildings, not least the whitewashed Winchester Center Congregational Church and Winchester Grange – the latter playing host to bustling flea markets, toe-tapping music nights and an annual Strawberry Festival. In nearby Winsted, the American Mural Project – the world's largest indoor collaborative art project – takes pride of place alongside the American Museum of Tort Law.

Activities

Find a laid-back lifestyle in Winchester

Small-town charm is alive and well in Winchester, and you'll find it in abundance at the town's delightful historic downtown. Shopping for one-of-a-kind buys in dusty antique stores, tucking into comfort food while watching an old arthouse film at an art deco-style theater and indulging your creative side at an artist-led pottery class are just a handful of the experiences that await. And if you love a good street party, the town comes up trumps with a calendar of colorful parades celebrating everything from the Laurel Festival to the pet pooches belonging to local schoolchildren.

Weather

Fall fever in Winchester

It's not too wild a statement to say that, should you decide to visit anywhere in New England in the fall, there's a good chance you won't be alone. Indeed, demand for Winchester vacation rentals can soar in the fall months, especially in November, when the Litchfield Hills are ablaze with rich autumnal shades. The destination is also popular over the summer months, with vacations between Memorial Day and Labor Day serving up sunny days and toasty temperatures. The winter season, although not without its charms, is fairly cold and not for the faint-hearted.

Natural features

Outdoor adventure near Winchester

You'll find an array of gorgeous green spaces within easy drive of Winchester vacation rentals, not least the wooded splendor of the American Legion State Forest, immediately east of the town. It's a 4-season hotspot for outdoor adventure. Visitors can hike the meandering Henry Buck Trail, enjoy a kayaking excursion along the "Wild and Scenic" Farmington River or partake in some of the region's best hunting. North-west of Winchester, the quaint stone observation tower at the summit of Haystack Mountain serves up unforgettable views, often as far as Long Island Sound.

How many vacation rentals are available around Winchester?

Our 2021 property listings offer a large selection of 59 vacation rentals around Winchester. From 50 house rentals to 2 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.