Winchester vacation rentals

We found 125 vacation rentals — enter your dates for availability

Discover a selection of 7 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.

Vacation rentals with weekly discounts - Winchester

Showing deals for:Mar 27 - Apr 3

Image gallery for Cozy Cabin in the Berkshires

Exterior
10 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)

Cozy Cabin in the Berkshires

Sandisfield

13% off
Price is $248
$1,739 for 7 nights
All fees included
Cozy Cabin in the Berkshires

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Winchester

Why visit Winchester

  1. Outdoor Activities: Enjoy a variety of recreational options, including fishing, canoeing, water skiing, and hiking trails around scenic Lake Winchester.
  2. Historical Landmarks: Explore the rich history of Winchester with its charming historic homes and cultural sites.
  3. Picturesque Landscapes: Experience the stunning natural beauty of Litchfield County, ideal for romantic getaways and relaxation.
  4. Family-Friendly Atmosphere: Winchester is perfect for families, offering activities and spaces that cater to visitors of all ages.
  5. Diverse Accommodations: Choose from a range of vacation rentals, from cozy apartments to waterfront cottages, ensuring a comfortable stay.

Popular types of accommodation in Winchester

Planning a getaway to Winchester? You're in for a treat! Discover the charm of this destination by choosing from popular vacation rentals such as Apart Hotels, cozy apartments, and houses. Whether you’re looking for a serene resort by the lake, a waterfront retreat, or an entire cottage near Danbury Highland Lake, Winchester has the perfect accommodation for your stay. Enjoy transparency and savings as you find your ideal home away from home!

  • Apartments: The top choice for vacation rentals in Winchester, offering convenience and comfort for travelers.
  • Houses: A great option for families or groups seeking more space and privacy during their stay.
  • Cabins: Ideal for nature enthusiasts, these rentals provide a charming escape in a serene environment.
  • Cottages: Perfect for a cozy getaway, these quaint homes offer a warm and inviting atmosphere.
  • Villas: A luxurious option for those wanting a sophisticated and spacious retreat.**

Top attractions in Winchester

Winchester, Connecticut, is perfect for outdoor enthusiasts and those seeking scenic romance. Visitors can explore national parks, local parks, and historic homes, offering a mix of culture and family-friendly experiences. Activities such as fishing, water skiing, canoeing, and hiking trails abound, making it an ideal destination for a lake vacation. Whether you're looking to relax or adventure, Winchester has something for everyone to enjoy.

  1. Highland Lake: A picturesque lake nestled in Winchester, perfect for a romantic getaway. Enjoy beach activities, scenic views, and outdoor adventures that make it a delightful spot for relaxation and recreation.
  2. Burr Pond State Park: Located 4 miles from Winchester, this state park offers thrilling outdoor adventures amidst beautiful scenery. Hiking, fishing, and picnicking opportunities abound, making it ideal for nature enthusiasts.
  3. Winchester Historical Society: Situated in Winchester, this history museum showcases the rich cultural heritage of the area. Explore exhibits that highlight local history and community stories, providing a fascinating glimpse into the past.

Things to do recommended for couples

Winchester offers delightful couple experiences! Enjoy skiing at Mohawk Mountain Ski Area, just 12 miles away, or indulge in wine tasting at Connecticut Valley Winery, 8 miles from town. For an evening of entertainment, catch a concert at Music Mountain, located 11 miles from Winchester.

Things to do recommended for families

During your family vacation in Winchester, you can enjoy fun at Laurel Lanes arcadeAdventureZone, relax at Satan's Kingdom State Recreation Area, and explore the beautiful Winding Trails, perfect for wellness and outdoor activities, all within a short drive from the town.

Things to do recommended for groups

Group travelers in Winchester can enjoy a night out at the Infinity Music Hall and Bistro, shop at Ames Plaza Shopping Center, or experience the thrill of motor racing at Lime Rock Park. Each venue offers a unique vibe perfect for creating memorable moments together.

What do I need to keep in mind when booking a vacation in Winchester

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, it's important to prioritize your preferences when searching. Here are some helpful booking tips for using Vrbo.

  • Traveling to Winchester with a group: Think about how many bedrooms you require, as well as additional features like a fully equipped kitchen or outdoor areas for group activities. Luckily, you can easily apply filters for these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities, like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Winchester: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, we invite you to explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Winchester

Winchester, Connecticut, offers a delightful mix of outdoor adventure and rich history. Explore the serene Lake Winchester for stunning views and recreational activities. The charming Town of Winchester invites you to enjoy its family-friendly atmosphere and historical landmarks. Nearby, Litchfield County showcases picturesque landscapes perfect for a romantic getaway. Whether you're seeking relaxation or exploration, Winchester and its surrounding towns promise an unforgettable vacation experience.

  • Colebrook: Located 4 miles from Winchester, Colebrook is a serene escape for outdoor enthusiasts and nature lovers. This charming town is known for its picturesque scenery, making it ideal for romantic getaways. Visitors can enjoy activities like skiing in the winter months and hiking or biking during warmer seasons. Notable local attractions include stunning lakes, expansive parks, and majestic mountains, offering ample opportunities for exploration and relaxation amidst nature's beauty.
  • Riverton: Situated 5 miles away from Winchester, Riverton is a vibrant destination that combines outdoor recreation with scenic views. This city is perfect for those seeking excitement, with attractions like local casinos and golf courses that cater to both thrill-seekers and leisure travelers. The nearby river and national state park enhance the area's natural charm, making it a great spot for fishing, hiking, and enjoying the great outdoors while taking in the breathtaking landscape.
  • Norfolk: Just 6 miles from Winchester, Norfolk is a delightful town known for its rich cultural experiences and outdoor activities. Visitors can immerse themselves in the local arts scene by attending theater performances or music concerts. The area's lakes and parks provide a beautiful backdrop for leisurely strolls or picnics, while nearby stadiums host exciting events. Norfolk's blend of romance, scenery, and vibrant community make it a must-visit destination for those exploring the region.

Best time to go to Winchester

If you're planning a trip to Winchester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.3°F (-3.7°C)Light RainMostly CloudyAverageAverage
February27.1°F (-2.7°C)Light RainMostly CloudyAverageSlightly Low
March34.5°F (1.4°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly CloudyModerately HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June65.3°F (18.5°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnyModerately HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyModerately HighAverage
October51.8°F (11.0°C)Light RainMostly SunnyModerately LowSlightly High
November39.7°F (4.3°C)Light RainMostly SunnyModerately LowAverage
December31.6°F (-0.2°C)Light RainMostly CloudyModerately LowSlightly Low

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. Being the planner definitely has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash™ on qualifying reservations. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient area to plan new trips, pick up right where you left off, or review and organize your travel plans. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 best area to stay in Winchester when booking a vacation rental?
When planning a vacation rental in Winchester, Connecticut, one of the best areas to consider is the charming neighborhood surrounding Lake Winchester. This picturesque area offers a serene lakeside experience, superb for those looking to unwind and enjoy nature. With numerous vacation rental properties available, you'll find options ranging from cozy cabins to spacious homes, suiting various group sizes and preferences.

Staying near Lake Winchester provides easy access to outdoor activities such as fishing, kayaking, and hiking along the scenic trails. A highlight of this area is the beautiful park that lines the lake, which is ideal for picnicking and enjoying the tranquil waters. Additionally, the nearby Indian Mountain State Park is another fantastic point of interest, offering various trails and stunning vistas that showcase the natural beauty of the region.

Another great option is the downtown area of Winsted, which combines a quaint small-town feel with local shops, restaurants, and cultural attractions. This vibrant community often has several vacation rental properties available, allowing visitors to immerse themselves in the local atmosphere.
How much does it cost to rent a vacation home in Winchester?
Prices for vacation rentals in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winchester vacation house rentals?
You can find great discounts on house rentals in Winchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Winchester?
A long-stay vacation rental in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Winchester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winchester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Winchester for a vacation rental?
The best time to book a vacation rental in Winchester is during the peak season from July to September. This vibrant period invites travelers eager to enjoy the warm summer days and explore the picturesque landscapes of Connecticut. With temperatures typically ranging from the mid-70s to low 80s Fahrenheit, it's an ideal climate for outdoor activities such as hiking, biking, and visiting local farms and markets.

July stands out as the most popular month, drawing families and adventure-seekers alike who flock to the area for its natural beauty and seasonal events. Enjoy leisurely strolls along the scenic trails or partake in community festivities that showcase the charm of Winchester. The lively atmosphere during this time enhances the overall experience, making it great for those seeking a blend of relaxation and adventure.

For travelers looking for more budget-friendly options, consider visiting in December. While this is considered the low season, it offers a unique opportunity to experience Winchester's cozy winter charm.
How early should I book a Winchester vacation rental?
Book your Winchester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchester?
In Winchester, visitors can enjoy a blend of natural beauty and historical sites. The picturesque town center features the charming Litchfield County Courthouse and is close to local shops and eateries that showcase the area's quaint character. For outdoor enthusiasts, the nearby Highland Lake offers opportunities for swimming, fishing, and kayaking, making it a popular spot during the warmer months.

The historic Bantam Lake, the largest natural lake in Connecticut, is also within reach and provides scenic views and recreational activities like hiking and birdwatching at the adjacent White Memorial Conservation Center.
Can I change or cancel my Winchester home rental booking on Vrbo?
To find Winchester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winchester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas