Where to stay around Winchester, CT?

Our 2018 property listings offer a large selection of 66 vacation rentals near Winchester. From 44 Houses to 15 Bungalows, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Winchester for a holiday or a weekend are on VRBO.

What are the popular point of interests near where I can stay when traveling to Winchester?

VRBO offers a large selection of vacation rentals near lovely places in Winchester. From VRBO travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Ski Butternut: 554 vacation rentals
  • Otis Ridge: 523 vacation rentals
  • Mohawk Mountain Ski Area: 231 vacation rentals
  • Connecticut Valley Winery: 184 vacation rentals
  • Litchfield Town Green: 212 vacation rentals

But there are many other points of interest around Winchester listed on VRBO where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Winchester?

Yes, of course. VRBO has 44 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Bungalows: 15 rentals available
  • Cabins: 15 rentals available
  • Cottages: 15 rentals available

Can I find a vacation rental with pool in Winchester?

Yes, you can select your prefered vacation rental with pool among our 16 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.

    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.

    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.

    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.

    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.

    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.