Winchester vacation rentals

We found 123 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:Feb 13 - Feb 20

Image gallery for Romantic and Secluded Berkshire's Gem

Living area
9.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)

Romantic and Secluded Berkshire's Gem

New Marlborough, MA

10% off
Price is CA $788
CA $6,894 total
includes taxes & fees
Romantic and Secluded Berkshire's Gem

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Winchester

Why visit Winchester

  • Stunning natural scenery: Enjoy beautiful lakes, state parks, and nature reserves that invite relaxation and outdoor adventures.
  • Historic landmarks: Explore the charming Winchester Castle, a key point of interest in the area.
  • Quaint neighborhoods: Discover family-friendly activities and picturesque spots perfect for picnics and leisurely strolls.
  • Romantic ambiance: Experience a lovely atmosphere ideal for a romantic getaway or peaceful retreat.
  • Diverse accommodation options: Choose from private homes, cozy cottages, and convenient hotels for a comfortable stay.

Popular types of accommodation in Winchester

If you're planning a getaway to Winchester, you'll find a variety of enticing vacation rental options to suit your needs. Our most popular types of accommodation include houses, charming cottages, and comfortable apartments. Whether you're looking for a cozy stay or a spacious retreat, Winchester has the perfect spot for you, along with convenient hotels and picturesque campsites to explore. Enjoy your stay with transparency and savings in mind.

  • Houses: The top choice for holidaymakers in Winchester, offering spacious and fully-equipped homes ideal for families or groups.
  • Cottages: Quaint and cozy, these charming retreats provide a picturesque getaway experience in the heart of nature.
  • Apartments: Convenient and comfortable, these rentals are perfect for those seeking a home-like atmosphere during their stay.
  • Cabins: Rustic and inviting, cabins offer a unique experience surrounded by the beauty of the outdoors.
  • Condos: Modern and stylish, condos provide a great blend of convenience and comfort for travelers.**

Top attractions in and around Winchester

Winchester, Connecticut, is perfect for a romantic getaway or outdoor adventure, offering stunning scenery and a variety of attractions. Explore nature reserves, state parks, and beautiful lakes that provide eco-friendly experiences. Visitors can enjoy outdoor activities and discover local points of interest, including the historic Winchester Castle. This charming destination promises memorable experiences for those seeking adventure and relaxation alike.

  • Highland Lake: Enjoy a picturesque escape at Highland Lake, boasting a lovely beach and stunning scenery. Perfect for outdoor activities, it's a romantic spot for couples or a peaceful retreat for families.
  • Burr Pond State Park: Just 6.4km away, Burr Pond State Park offers thrilling adventures among breathtaking natural beauty. With hiking trails and serene ponds, it's an ideal destination for outdoor enthusiasts.
  • Norfolk Historical Museum: Located 9.7km from Winchester, this museum immerses you in local culture and history. Explore fascinating exhibits that showcase the rich heritage of the area.

Things to do recommended for couples

For a romantic getaway in Winchester, explore the slopes at Mohawk Mountain Ski Area or Ski Sundown for thrilling winter sports. Don’t miss the enchanting Sunset Meadow Vineyards, where you can enjoy delightful wine and create memorable moments together amidst beautiful scenery.

Things to do recommended for families

During your family vacation in Winchester, explore the serene Satan's Kingdom State Recreation Area and Winding Trails for relaxation. For some adventurous fun, visit Laurel Lanes, an arcade adventure zone right in town, perfect for family bonding and excitement.

Things to do recommended for groups

Groups visiting Winchester can enjoy thrilling races at Lime Rock Park, shop and dine at Canton Green Shopping Center, and explore the delightful offerings at Rosedale Farms & Vineyards, all within a short drive from the town.

*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

Whether you're travelling with a group, family, pets, or planning an extended stay, be sure to filter your options based on what matters most to you. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Winchester with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winchester with young kids: Traveling with young children can present some difficulties. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your location relative to family-friendly attractions is advisable.
  • Taking your pets with you to Winchester: For many families, a vacation isn’t truly enjoyable without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Winchester: If you're in search of vacation rentals offering 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 features like parking, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay in Winchester

Winchester, Connecticut, offers a charming blend of outdoor beauty and romantic vibes, perfect for a memorable getaway. Explore scenic parks and tranquil lakes that invite relaxation and adventure alike. Nearby, discover quaint neighborhoods brimming with family-friendly activities and lovely locations for a picnic. The warmer months bring a delightful atmosphere, ideal for leisurely strolls and enjoying the fresh air. Experience the best of both recreation and romance in this picturesque village.

  • Winsted: Nestled within the heart of Winchester, Winsted is a charming city that offers visitors a delightful blend of outdoor activities and stunning natural scenery. Known for its romantic ambiance, Winsted is ideal for couples and nature enthusiasts alike. The area boasts access to ski fields and recreational areas, making it a perfect winter getaway. Notable landmarks include picturesque lakes, a national state park, and inviting beaches, providing plenty of options for relaxation and exploration. Whether you're skiing in the winter or hiking during the warmer months, Winsted promises a memorable adventure.
  • Colebrook: Located a mere 6.4km from Winchester, Colebrook is a serene city that captivates visitors with its breathtaking landscapes and outdoor opportunities. Known for its romantic setting, Colebrook is a haven for those seeking tranquility and adventure. The area features ski fields and recreational areas, making it a popular destination for winter sports enthusiasts. Local attractions include beautiful lakes, scenic mountains, and a national state park, all of which invite exploration and appreciation of nature's beauty. Colebrook is perfect for anyone looking to escape the hustle and bustle of city life.
  • Riverton: Just 8.0km away from Winchester, Riverton is a quaint city that offers a unique blend of outdoor adventures and scenic beauty. It’s a great spot for golf enthusiasts, with access to private clubs and resorts. Riverton’s charm lies in its picturesque lakes, winding rivers, and proximity to a national state park, all providing ample opportunities for hiking, fishing, and relaxing by the water. The romantic atmosphere makes it an ideal destination for couples looking to unwind and experience the great outdoors together.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Plus, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, seamlessly continue from where you last left off, or easily view and organize your travel plans. You can find your saved or booked properties neatly sorted into categories such as Potential, Upcoming, or Current Trips. To begin utilizing 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)
  • Lost Acres Vineyard (14.1 mi / 22.6 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)
  • Enders State Forest (12 mi / 19.3 km)
  • Mohawk Mountain State Forest (12.2 mi / 19.6 km)
  • Great Falls (13.6 mi / 21.8 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 charming neighbourhood of Winsted is an excellent choice. This area is not only rich in history but also boasts a friendly setting, making it ideal for visitors seeking both relaxation and adventure. Winsted is home to the picturesque Highland Lake, which provides opportunities for swimming, fishing, and picnicking, allowing guests to immerse themselves in the natural beauty of the region. Additionally, the historic downtown area features quaint shops and delightful eateries, great for leisurely strolls and local cuisine.
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?
July is the most popular time to visit Winchester, Connecticut, as it falls within the peak season that extends from July to September. During these summer months, the town comes alive with vibrant outdoor activities, making it ideal for travellers. With warm temperatures averaging around 26°C, you can comfortably explore local parks, take part in community events, or enjoy picnics by the scenic Farmington River.

The atmosphere in July is particularly lively, with visitors flocking to enjoy the picturesque landscapes and historical sites. It's a wonderful time for outdoor pursuits such as hiking, biking, or simply soaking in the beauty of the surrounding nature. For those interested in culture, the town often hosts summer festivals and live performances that add to the charm of this season.

If you're seeking a more budget-friendly option, consider planning your trip in December. While this month is quieter, it offers a great experience with the opportunity to enjoy peaceful winter walks and the festive vacation spirit. The charm of Winchester during the vacation season, with its quaint shops and decorated streets, can be a delightful experience away from the bustling summer 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 explore several charming attractions and enjoy the picturesque surroundings. The town's centrepiece is Lake Winchester, where guests can enjoy various outdoor activities such as fishing, kayaking, and hiking along the scenic trails. Nearby, the historic downtown area offers quaint shops, local eateries, and a glimpse into the town's rich history.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

More Vacation Ideas