Winchester Vacation Rentals, Winsted: Whole House to Yourself

Discover a selection of 5 homes and other vacation rentals in Winchester that are perfect for your trip. Vacation rentals provide the best amenities for you and your friends, family, or even pets, such as a fireplace and a washer and dryer. You're sure to find a rental that has what everyone needs, including options that are accessible or non-smoking.

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Find the best place to stay - Winchester

Beautiful 5BR Lake House on Highland Lake

Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!

Sleeps 12 · 5 bedrooms · 3+ bathrooms

Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!

Sleeps 9 · 4 bedrooms · 2 bathrooms

Top rated rentals - Winchester

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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.

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.

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.

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 to and around Winchester

Fly into Bradley Intl. Airport (BDL), the closest airport, located 21.9 mi (35.2 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 25.8 mi (41.5 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Winchester?

Houses are the most popular kind of vacation rental in Winchester, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in a variety of sizes and shapes. Explore our options to find your ideal fit.

How much does it cost to rent a vacation rental in Winchester?

Several factors influence how much you'll pay for a vacation rental in Winchester, like the season, type of property and length of stay. But, all our vacation homes have something in common — amazing value. Simply enter your travel dates to find your perfect fit.

How much does it cost to rent a beach house in Winchester?

The average price for a vacation rental close to the beach in Winchester will depend on when you'll be there and the type and size of property you want. You can find prices easily and quickly on Vrbo by entering your dates of travel. Then use the handy filter tool to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Winchester?

Happily, yes. You'll find eight vacation rentals that welcome pets in Winchester on Vrbo. Our cuddly best friends also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to book a perfect pad where Rover can join the fun.

What are popular rental amenities in Winchester?

Some of the most popular rental amenities people are looking for in Winchester include a lake view, nearby museums and a nearby waterfront. Whether you're traveling with family, your besties or even pets, Vrbo vacation rentals have the best amenities for making new memories with the people who matter most.

Are there large group vacation rentals in Winchester?

With six Winchester properties that can accommodate five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a birthday party, we'll help you book the ideal space for the occasion.

Are there vacation rentals in Winchester that welcome kids?

With eight family-friendly vacation properties available in Winchester, now is a superb time to introduce the kids to the joys of travel. Simply click on our "Properties good for families" filter box to search for stays that come with conveniences ideal for vacationing families, such as living rooms, patios, hot tubs and bunk beds.

What are the top attractions for families in Winchester?

Keep the kids amused at these leading family-friendly attractions in Winchester:

Winchester Historical Society
Laurel Lanes
Highland Lake

Can I find two-bedroom vacation rentals in Winchester?

Gather your nearest and dearest and experience complete comfort and privacy in one of the three two-bedroom vacation homes Winchester has to offer.

Are there vacation rentals with WiFi in Winchester?

You can choose from six vacation rentals with WiFi in Winchester. If you'd like to disconnect from the world while on vacation, but still want to be connected to the web, these properties are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Winchester?

Pick from eight Vrbo vacation rentals with air conditioning in Winchester offering that cool, cool breeze and extra touch of comfort. Simply enter your travel dates and then make use of our filters to look for stays with air conditioning.

How old do you have to be to rent a vacation rental in Winchester?

Age restrictions can differ between properties on Vrbo, so check the rules of the vacation home in Winchester you want. But in general, it's 16, 18 or 21.