Winchester vacation rentals

We found 125 vacation rentals — enter your dates for availability
Discover a selection of 10 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 out more about Winchester

Why visit Winchester

  • Outdoor Adventures: Winchester is a haven for nature lovers, offering a variety of state parks and nature reserves ideal for hiking and picnicking.
  • Scenic Landscapes: The picturesque surroundings provide a romantic atmosphere perfect for leisurely strolls and relaxation.
  • Family-Friendly Activities: Nearby Winsted features attractions that cater to families, ensuring fun for all ages.
  • Charming Local Parks: Explore the serene atmosphere of local parks, making it an ideal spot for eco-friendly experiences.
  • Accommodation Variety: Enjoy a range of holiday rentals, from private homes to cozy cottages, suited to every traveler's needs.

Popular types of accommodation in Winchester

Planning a getaway to Winchester? The excitement begins with selecting your accommodation. Discover a variety of popular holiday rentals, including private homes, charming cottages, and modern apartments. Whether you're searching for house rentals or looking to explore unique rental options, Winchester has something to suit every traveller's needs. Enjoy your stay with the reassurance of transparency and savings as you find the perfect spot to unwind and create lasting memories.

  • Private Holiday Homes: These spacious, fully-equipped homes offer the comforts of home, perfect for families or groups seeking privacy and convenience during their stay in Winchester.
  • Cottages: Charming and often quaint, these cottages provide a cozy retreat, ideal for those looking to enjoy a peaceful getaway in nature.
  • Apartments: Modern and stylish, these self-contained units are perfect for couples or solo travellers wanting easy access to local amenities.
  • Cabins: Nestled in serene settings, these rustic cabins are perfect for nature lovers, offering a unique experience close to the outdoors.
  • Chalets: Often located in picturesque areas, chalets provide a charming atmosphere, ideal for those seeking a tranquil escape.**

Top attractions in and around Winchester

Winchester, Connecticut offers a delightful escape for those seeking outdoor adventures and romantic scenery. Visitors can explore a variety of nature reserves, state parks, and local parks that cater to eco-friendly experiences. Whether you're hiking, picnicking, or simply enjoying the natural beauty, Winchester provides ample opportunities for adventure and relaxation amidst its stunning landscapes.

  • Highland Lake: Experience the serene beauty of Highland Lake, perfect for a romantic getaway or outdoor activities. Enjoy the scenic views, relax on the beach, and soak in the tranquil atmosphere.
  • Lime Rock Park: A thrilling destination for motorsport enthusiasts, Lime Rock Park offers exhilarating races and adventure. With its vibrant atmosphere, it’s a must-visit for those seeking excitement.
  • Burr Pond State Park: Immerse yourself in nature at Burr Pond State Park, where outdoor adventures await. Explore picturesque scenery, hiking trails, and opportunities for fun in the great outdoors.

Things to do recommended for couples

Winchester offers a charming getaway for couples. Enjoy a leisurely hike at the scenic Lake Winchester, followed by a picnic in the park. Explore quaint local shops and dine at cozy restaurants, making every moment a delightful experience together in this picturesque town.

Things to do recommended for families

Families can explore the scenic beauty of Winchester’s parks, such as the serene Lake Wononscopomuc, perfect for picnics and swimming. Enjoy hiking trails at the nearby Land Trust, or visit local farms for fresh produce and seasonal activities, creating memorable moments together.

Things to do recommended for groups

Experience the thrill of motor racing at Lime Rock Park, just 23km from Winchester. This exciting venue offers adrenaline-pumping events, perfect for group camaraderie, surrounded by the beautiful Connecticut landscape.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

If you're travelling with a group, enjoying a family getaway, bringing along your pets, or seeking longer stays, it's important to filter your options based on what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require and any amenities you might want, like a full kitchen or outdoor space for gatherings. Thankfully, you can easily filter for these features and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Winchester: For many families, a trip isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo properties that are pet-friendly. Most of these accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals with special offers 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 preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Winchester

Winchester, Connecticut, offers a charming escape for those seeking outdoor adventures and romantic getaways. Explore the picturesque landscapes and enjoy recreational activities in the nearby city of Winsted, where family-friendly attractions abound. The serene atmosphere of Winchester District 6 invites relaxation and scenic strolls, making it an ideal destination for nature enthusiasts and couples alike. Uncover the beauty and tranquility of this hidden gem in New England during your holiday.

  • Colebrook: Nestled just 6km from Winchester, Colebrook offers a picturesque escape into nature, making it a perfect destination for outdoor enthusiasts and families alike. Visitors can explore its recreational areas, enjoy skiing in the winter, or simply take in the stunning views of lakes, parks, and forests. Whether you're looking for a romantic getaway or a fun-filled day with the family, Colebrook's serene environment and numerous outdoor activities provide a refreshing experience away from the hustle and bustle.
  • Riverton: Located 8km from Winchester, Riverton is a charming city known for its stunning scenery and outdoor adventures. It's an ideal spot for couples seeking a romantic outing or anyone wanting to enjoy the great outdoors. Popular activities include golfing and theatre performances, while the nearby national state park and river offer breathtaking natural beauty. Riverton's recreational areas are perfect for picnics or leisurely strolls, making it a delightful place to unwind and appreciate the landscape.
  • West Hill Lake: Just 8km away from Winchester, West Hill Lake is a quaint village that attracts visitors for its scenic beauty and outdoor activities. This picturesque area is ideal for those seeking a romantic escape or a peaceful day by the water. With opportunities for golfing, theatre, and various recreational activities, it's a perfect spot for relaxation. The nearby lake, beach, and urban park provide ample options for leisurely activities, making West Hill Lake a serene retreat for nature lovers.

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 CloudyAverageSlightly Low
February27.1°F (-2.7°C)Light RainMostly CloudyAverageAverage
March34.5°F (1.4°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly CloudyModerately HighSlightly Low
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 LowAverage
November39.7°F (4.3°C)Light RainMostly SunnyModerately LowAverage
December31.6°F (-0.2°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save some money on your upcoming trip? One way to do this is by being flexible with your travel dates, as prices can vary quite a bit. Additionally, booking a longer stay often leads to significant savings. To help you find the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing itineraries, or review your bookings with ease. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Winchester getaway

Learn about the unique charm of Winchester with a stay in a private vacation home. There's no shortage of things to see and do in the area.Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Winchester

Are you hoping to find attractions to see in the city? Venture out of your vacation home and check out everything that makes Winchester a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Connecticut Valley Winery (8.3 mi / 13.4 km)
  • Ski Sundown (9.4 mi / 15.2 km)
  • Sunset Meadow Vineyards (11.1 mi / 17.9 km)
  • Mohawk Mountain Ski Area (12.4 mi / 19.9 km)
  • Flamig Farm (13.5 mi / 21.7 km)
  • Umpachene Falls Park (13.7 mi / 22 km)

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to appreciate the scenery, Winchester is a great spot to appreciate mother nature. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Highland Lake (2.6 mi / 4.3 km)
  • Satan's Kingdom State Recreation Area (9.5 mi / 15.4 km)
  • Woodridge Lake (11.5 mi / 18.6 km)
  • Harwinton Conservation and Recreation Area (11.7 mi / 18.8 km)
  • Enders State Forest (12 mi / 19.3 km)
  • Mohawk Mountain State Forest (12.2 mi / 19.6 km)

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 considering a vacation rental in Winchester, Connecticut, the town itself offers a charming atmosphere with several appealing neighbourhoods. One of the best areas to stay in is the picturesque town centre, where you can enjoy a delightful blend of historic architecture and modern amenities. This area is close to the charming Town Green, a lovely spot for leisurely strolls and community events.

Another great option is around the scenic Highland Lake, which provides stunning views and opportunities for outdoor activities such as kayaking and fishing. The lake area is also home to parks and walking trails, making it ideal for nature enthusiasts.

In terms of vacation rentals, there are a variety of properties available throughout the town, suiting different preferences and group sizes.
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 travelling 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.
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. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 travellers 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 visit Winchester for a vacation rental is during the peak season from July to September. This vibrant period draws families and outdoor enthusiasts looking to enjoy the picturesque surroundings of Connecticut. With the warm summer temperatures typically ranging from 20 to 30 degrees Celsius, it's superb for exploring the charming local parks, hiking trails, and engaging in various water activities at nearby lakes.

July stands out as the most popular month, offering a bustling atmosphere filled with events and activities. Visitors can take advantage of the long days to embark on scenic hikes, visit local farmers' markets, or enjoy outdoor picnics amidst the beautiful natural landscape.

For those who prefer a quieter experience and are looking for better value, consider visiting in December. While it's the low season, Winchester transforms into a winter wonderland, ideal for cosy getaways. The vacation spirit is palpable, and you can enjoy the festive decorations and seasonal activities, making it a delightful time to explore the town's charm without the crowds.
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, Connecticut, visitors can enjoy a variety of attractions that highlight the area's natural beauty and historical significance. The picturesque Lake Winchester is a popular spot for outdoor activities such as fishing, boating, and swimming during the warmer months, providing a relaxing retreat for nature lovers.

The nearby Park Pond is another delightful location for picnics and leisurely walks, surrounded by scenic views and lush greenery. For those interested in history, the town's historical sites, including the Winchester Historical Society, offer insights into the local heritage and culture.

Additionally, the charming town centre features quaint shops and local eateries, superb for a leisurely afternoon stroll.
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 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 travellers 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 cosy cabin or a beach house, 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.

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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

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