Find Vacation Rentals in Winchester Center

We have 17 properties to choose from
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Popular Winchester Center Vacation Rentals

Find the perfect Winchester Center vacation rental

House Winchester
from $344 per night
House ∙ 12 guests ∙ 6 bedrooms

186 m² House

5.0
Outstanding(36 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Apartment Winchester
from $175 per night
4 guests ∙ 2 bedrooms

Apartment

4.9
Outstanding(16 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
House Winchester
from $272 per night
House ∙ 7 guests ∙ 3 bedrooms

121 m² House

5.0
Outstanding(65 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Cottage Winchester
from $236 per night
4 guests ∙ 2 bedrooms

Cottage

5.0
Outstanding(7 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Apartment Winchester
from $146 per night
3 guests ∙ 1 bedroom

Apartment

4.6
Excellent(37 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Cottage Winchester
from $259 per night
6 guests ∙ 2 bedrooms

Cottage

5.0
Outstanding(27 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Cottage Winchester
from $314 per night
Cottage ∙ 6 guests ∙ 2 bedrooms

58 m² Cottage

5.0
Outstanding(53 ratings)
Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
Apartment Winchester
from $350 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

102 m² Apartment

Winchester, Litchfield County, Connecticut, United States
Vrbo
Details
House Winchester
from $433 per night
House ∙ 12 guests ∙ 6 bedrooms

186 m² House

Winchester, Litchfield County, Connecticut, United States
Vio.com
Details
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Recommended Rentals With Pools

House  Winchester
from $1,907 per night
12 guests ∙ 5 bedrooms

House

5.0
Outstanding(8 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
Vrbo
Details
House  Winchester
from $1,117 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(2 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
Vrbo
Details
House  Winchester
from $672 per night
House ∙ 6 guests ∙ 3 bedrooms

307 m² House

5.0
Outstanding(3 ratings)
Winchester, Litchfield County, Connecticut, United States
Pool
Vrbo
Details
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Vacation Homes With Terraces

Cottage  Winchester
from $215 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

93 m² Cottage

Winchester, Litchfield County, Connecticut, United States
Balcony/Patio
Vrbo
Details
House  Winchester
from $729 per night
10 guests ∙ 4 bedrooms

House

Winchester, Litchfield County, Connecticut, United States
Balcony/Patio
Vrbo
Details
House  Winchester
from $112 per night
2 guests ∙ 2 bedrooms

House

Winchester, Litchfield County, Connecticut, United States
Balcony/Patio
Vrbo
Details
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Cabins and Homes With Fireplaces

Bed and breakfast  Winchester
from $349 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

M2 Deluxe Suite

4.7
Excellent(99 ratings)
Winchester, Litchfield County, Connecticut, United States
Fireplace
HomeToGo
Details
Bed and breakfast  Winchester
from $235 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

C2 Carriage House

4.7
Excellent(99 ratings)
Winchester, Litchfield County, Connecticut, United States
Fireplace
HomeToGo
Details
Bed and breakfast  Winchester
from $350 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom

M1 Deluxe Suite

4.7
Excellent(99 ratings)
Winchester, Litchfield County, Connecticut, United States
Fireplace
HomeToGo
Details
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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 $110 per night.

How many vacation rentals are available in Winchester Center?

You can find 17 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.

What are the trendiest neighborhoods Winchester?

Popular Day Trips Near Winchester Center

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