Choose from 17 vacation rentals located in Winchester, Connecticut. Top filters in Winchester include Internet / Wifi, Air conditioner, and Parking. Prices range from $88 to $456 per night. Our most popular vacation rental types near Winchester are Apartment and Hotel.

Top vacation rentals in Winchester

Property view
9.9 / 10.0
Outstanding(42 Ratings)
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
Cottage
 in Winchester
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen or Kitchenette

This Cottage for $304 in Winchester, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
9.4 / 10.0
Outstanding(12 Ratings)
Lakeridge Litchfield Resort Townhome Pool Tennis Skiing
House
 in Torrington
4 guests · 2 bedrooms · 2 baths
Pool · Pets allowed · Kitchen or Kitchenette

Looking for a House in Winchester, this House for $154 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Beach
9.9 / 10.0
Outstanding(88 Ratings)
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
House
 in Winchester
12 guests · 6 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Winchester? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Miscellaneous
10.0 / 10.0
Outstanding(18 Ratings)
Fall 2024! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c and heat.
Cottage
 in Winsted
6 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Enjoy the best of Winchester in our Cottage, Fall 2024! Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c and heat.. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Search by amenity

Vacation rentals with internet & wifi in Winchester

Terrace/patio
No ratings yet
Lovely 3 Bedroom Townhouse , perfect for skiing
Apartment
 in Torrington
4 guests · 3 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our Apartment in Winchester has everything you need for a rejuvenating stay. Treat yourself to Lovely 3 Bedroom Townhouse , perfect for skiing's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Beach nearby, sun loungers, beach towels
10.0 / 10.0
Outstanding(4 Ratings)
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Cottage
 in Winsted
4 guests · 2 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Winchester at The Cottage at Highland Lake, year-round, waterfront with a boat dock for $239 for your next trip.

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Room
No ratings yet
Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.
Cottage
 in Winsted
4 guests · 2 bedrooms · 1 bath
Pets allowed · Internet / Wifi

Nestled in Winchester, this Cottage is perfect for your next vacation. Enjoy Cottage Ease. Quaint cottage nestled in on Higland lake Winsted, Ct.'s top-rated amenities, including Internet / Wifi and Pets allowed, and more.

$$$$
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Outdoor dining
No ratings yet
Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Apartment
 in Torrington
9 guests · 4 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner

Looking to create some memories in Winchester? Look no further than our Apartment, Spacious 4-bedroom condo with AC and WiFi in Litchfield County. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Winchester

Winchester travel guide

Let us help you plan your perfect Winchester vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winchester, and more.

Frequently asked questions

What do i need to know before visiting Winchester, ct?

Before visiting Winchester, CT, here are a few things to keep in mind:

  • The town is home to several hiking trails and parks, so be sure to bring comfortable shoes.
  • The town is situated in the Litchfield Hills of Connecticut, so the climate is mild and humid.
  • The area is rural and wooded, so it's a great place to enjoy nature.

Additionally, there are plenty of cultural attractions in town, such as the historic Watson-Curtze Mansion, local art galleries, and the Winchester Historical Society.

What are the must-visit tourist attractions in Winchester, ct?

Winchester, CT is a small town with plenty of attractions to explore. Here are the must-visit tourist attractions in Winchester, CT:

  • Winchester Center Historic District
  • Winchester Center Congregational Church
  • Winchester Historical Society Museum
  • Winchester Town Green

The Winchester Center Historic District is a great place to start your exploration of Winchester, CT. It is a designated historic district that includes the town green, a Congregational Church, and several other buildings. The Winchester Historical Society Museum is also a great place to learn about the history of the town. Finally, the Winchester Town Green is a great spot to relax and take in the beauty of the area.

How can i get around in Winchester, ct?

You can get around in Winchester, CT in a few different ways:

  • By car
  • By bike
  • By foot

The town is small enough to walk or bike around, and there is plenty of parking available for cars.

Where can i find affordable accommodation in Winchester, ct?

Winchester, CT offers a variety of affordable accommodation options for visitors. Here are four that are worth considering:

  • The Winchester Inn – a historic bed and breakfast with competitively priced rooms and a convenient location.
  • The Winchester Hotel – a budget-friendly hotel with basic amenities and a good location.
  • The Winchester Hostel – a great option for those looking for a low-cost stay in the area.
  • The Winchester Motel – a reasonably priced motel with basic amenities and a convenient location.

No matter what type of accommodation you're looking for, Winchester, CT has something to suit your needs and budget.

What is the culture like in Winchester, ct?

Winchester, CT is a small town in Litchfield County with a population of just over 11,000. It has a rich history that dates back to the 1700s, and its culture is a mix of the small-town values of the past and the modern day amenities of the present. Here are five aspects of Winchester's culture:

  • The town is home to several parks, trails, and outdoor spaces, providing plenty of opportunity for outdoor recreation.
  • The local theater group, the Winchester Players, puts on productions throughout the year.
  • The town celebrates its heritage with events like the Winchester Festival and the annual Fall Foliage Festival.
  • There is a thriving local arts scene, with galleries, studios, and venues for live performances.
  • The town is home to a variety of restaurants, from family-run establishments to upscale eateries.

Is Winchester, ct safe to travel to?

Winchester, CT is generally a safe place to travel to. Here are some tips to ensure your safety:

  • Stay in well-lit areas at night
  • Be aware of your surroundings
  • Familiarize yourself with the area

Make sure to take the necessary precautions when traveling to any new place.

What are the popular shopping destinations in Winchester, ct?

Winchester, CT is home to some popular shopping destinations, including:

  • Winchester Center Shopping Center
  • Winchester Mall
  • The Shoppes at Winchester

These shopping centers offer a variety of stores, restaurants, and services for locals and visitors alike.

What are the best neighborhoods to visit in Winchester, ct?

Winchester, CT has plenty of great neighborhoods to explore. Here are just a few of the best:

  • Duck River: known for its beautiful views of the river and its abundance of outdoor activities
  • Upper Westside: an up-and-coming neighborhood with plenty of shops and restaurants
  • Westside Hill: a historic district with a variety of architectural styles

Where is Winchester, ct?

Winchester, CT is a small town located in Litchfield County in the Northwestern part of the state. It is a rural town with a population of about 11,000 people and is known for its rolling hills and scenic views. It also is home to a variety of outdoor recreational activities including hiking, biking, and skiing.

What are the most popular vacation rental amenities in Winchester, ct?

The most popular vacation rental amenities in Winchester, CT, include:

  • Fully-equipped kitchens
  • High-speed internet
  • Spacious living areas
  • Outdoor patios or decks
  • Washer/dryer

These amenities provide visitors with the opportunity to stay in a comfortable and convenient environment. Fully-equipped kitchens allow guests to make their own meals, while high-speed internet allows them to stay connected to the outside world. Spacious living areas give guests plenty of room to relax and unwind. Outdoor patios or decks provide a nice place to enjoy the outdoors, and a washer/dryer is a great way to keep clothes clean during a stay.

What are the top things to do in Winchester, ct?

Winchester, CT is a great place to explore and enjoy the outdoors. Here are some of the top things to do in the area:

  • Explore the Winchester Nature Center
  • Go fishing at Winchester Lake
  • Visit the Winchester Historical Society Museum
  • Hike the trails at the White Memorial Conservation Center

Whether you're looking to appreciate nature or learn about the area's rich history, there's something for everyone in Winchester, CT.

What is the price range for rentals in Winchester?

Vacation rentals in Winchester have a price range between $88-$456. The average price for rentals in Winchester is $237 per night.

What are the most popular vacation rental amenities in Winchester?

  • Internet / Wifi
  • Air conditioner
  • Parking

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