Discover a selection of 83 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 air conditioning. Prices start at $111 per night, and houses and cottages 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.

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 to get there

How to get to and around Winchester

Fly into Bradley Intl. Airport (BDL), the closest airport, located 21.5 mi (34.5 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Westfield, MA (BAF-Barnes Municipal), which is 26 mi (41.9 km) away.

How many vacation rentals are available around Winchester?

Our 2022 property listings offer a large selection of 83 vacation rentals around Winchester. From 68 house rentals to 13 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Winchester?

Yes, of course. Vrbo has 68 Houses in Winchester. Our other popular types of vacation rentals in Winchester include:

  • Cottages: 13 rentals available
  • Cabins: 13 rentals available
  • Bungalows: 13 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Winchester?

Yes, you can select your preferred vacation rental with pool among our 20 vacation rentals with pool available in Winchester. Please use our search bar to access the selection of vacation rentals available.