Find Vacation Rentals in Winchester Center

We have 15 properties to choose from
Winchester
Anytime
Guests
Winchester
Anytime
Guests

Popular Winchester Center Vacation Rentals

Find the perfect Winchester Center vacation rental

House Winchester
$360 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (104 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Winchester
$317 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding (5 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Winchester
$237 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding (58 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
House Winchester
$402 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (32 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
Apartment Winchester
$136 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
4.7
Excellent (6 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
Cottage Winchester
$334 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
Cottage Winchester
$326 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (51 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
Apartment Winchester
$146 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
Outstanding (12 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
Apartment Winchester
$146 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.7
Excellent (53 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
Details
Details
View more

Recommended Rentals With Pools

Bed and breakfast  Winchester
$158 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom
4.8
Outstanding (36 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
Details
Expedia
Details
Details
House  Winchester
$417 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (54 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
Details
Vrbo
Details
Details
Condo  Winchester
$148 per night
Condo ∙ 4 guests ∙ 3 bedrooms
Winchester, Litchfield County, Connecticut, United States
Pool
Details
Vrbo
Details
Details
View more

Pet-Friendly Homes and Apartments

Cottage  Winchester
$293 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (214 ratings)
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Winchester
$105 per night
House ∙ 5 guests ∙ 2 bedrooms
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
Details
Vrbo
Details
Details
Cabin  Winchester
$157 per night
Cabin ∙ 5 guests ∙ 1 bedroom
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
Details
Vrbo
Details
Details
View more

Best vacation rentals with a balcony

Bed and breakfast  Winchester
$308 per night
Bed and breakfast ∙ 8 guests ∙ 1 bedroom
4.6
Excellent (129 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
Details
Expedia
Details
Details
Cottage  Winchester
$210 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (38 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
Details
Vrbo
Details
Details
House  Winchester
$1,844 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (4 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

Can I find cheap vacation rentals in Winchester Center?

Prices for a stay in Winchester Center begin at $105 per night.

How many vacation rentals are available in Winchester Center?

You can find 15 available vacation rentals in Winchester Center.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winchester Center

Find the best Winchester Center vacation rentals on Tripping.com. With over 101 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Winchester Center range from $48 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 82 homes in Winchester Center offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 20 rentals with pool or jacuzzi, or relax with the family in one of the 73 homes with cable TV. For all those pet owners with dogs or cats, Winchester Center offers 32 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 7 vacation rental sites in Winchester Center where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 62 HomeAway rentals, 10 Booking.com short term rentals and 9 TripAdvisor vacation rentals.

Popular Day Trips Near Winchester Center

Show more

What are the trendiest neighborhoods Winchester?

image-tag