Find Vacation Rentals in Winchester Center

We have 16 properties to choose from
Winchester
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Popular Winchester Center Vacation Rentals

Find the perfect Winchester Center vacation rental

House Winchester
$230 per night
House ∙ 5 guests ∙ 3 bedrooms
5.0
"Excellent" (38 ratings)
Winchester, Litchfield County, Connecticut, United States
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Vrbo
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Apartment Winchester
$93 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winchester, Litchfield County, Connecticut, United States
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Vrbo
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Cottage Winchester
$309 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (46 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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Cottage Winchester
$315 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (23 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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House Winchester
$236 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
"Excellent" (53 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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House Winchester
$177 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
"Excellent" (110 ratings)
Winchester, Litchfield County, Connecticut, United States
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Vrbo
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Apartment Winchester
$84 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.8
"Excellent" (38 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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Apartment Winchester
$121 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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House Winchester
$324 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
"Excellent" (17 ratings)
Winchester, Litchfield County, Connecticut, United States
Details
Vrbo
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Recommended Rentals With Pools

Condo Pool Winchester
$146 per night
Condo ∙ 4 guests ∙ 3 bedrooms
Winchester, Litchfield County, Connecticut, United States
Pool
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Vrbo
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House Pool Winchester
$121 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (17 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
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Vrbo
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House Pool Winchester
$344 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (61 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

House Pet-friendly Winchester
$160 per night
House ∙ 5 guests ∙ 2 bedrooms
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Winchester
$609 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (2 ratings)
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
Details
Vrbo
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Details
Cottage Pet-friendly Winchester
$291 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (170 ratings)
Winchester, Litchfield County, Connecticut, United States
Pet-friendly
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Vrbo
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Best vacation rentals with a balcony

Cottage Balcony Winchester
$198 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (35 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
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Vrbo
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Apartment Balcony Winchester
$211 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
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Vrbo
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Bed & Breakfast Balcony Winchester
$381 per night
Bed & Breakfast ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (75 ratings)
Winchester, Litchfield County, Connecticut, United States
Balcony
Details
HomeToGo
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Frequently Asked Questions

Can I find cheap vacation rentals in Winchester Center?

Prices for a stay in Winchester Center begin at $85 per night.

How many vacation rentals are available in Winchester Center?

You can find 16 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

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