Find Vacation Rentals in Winchester

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Winchester
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
$145 per night
House ∙ 2 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
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Vrbo
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Apartment Winchester
$152 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (18 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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House Winchester
$207 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
"Excellent" (57 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Details
Apartment Winchester
$173 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Farmhouse Winchester
$132 per night
Farmhouse ∙ 4 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Apartment Winchester
$138 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Condo Winchester
$303 per night
Condo ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Condo Winchester
$215 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (3 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
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Condo Winchester
$219 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (4 ratings)
Winchester, Middlesex County, Massachusetts, United States
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Vrbo
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Recommended Rentals With Pools

Apartment Pool Winchester
$265 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.5
"Outstanding" (18 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
Vrbo
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Apartment Pool Winchester
$229 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
"Excellent" (11 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
Vrbo
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Apartment Pool Winchester
$396 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Pool
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Vrbo
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Pet-Friendly Homes and Apartments

House Pet-friendly Winchester
$186 per night
House ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Winchester
$137 per night
House ∙ 2 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
Vrbo
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House Pet-friendly Winchester
$463 per night
House ∙ 2 guests ∙ 4 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
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Vrbo
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Best vacation rentals with a balcony

Condo Balcony Winchester
$207 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (5 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
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Condo Balcony Winchester
$237 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (3 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
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Condo Balcony Winchester
$373 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
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Frequently Asked Questions

Is renting a vacation home in Winchester expensive?

Usually, a stay in Winchester starts at $110 per night.

Are there any vacation rentals available to book in Winchester?

On tripping.com, you will find 437 available vacation rental offers in Winchester.

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

Looking for a vacation rental in Winchester? Tripping.com has 36 vacation rental homes available in Winchester. You'll find 0 studios, 20 1-bedroom, 7 2-bedroom and 9 rentals with 3 or more bedrooms ranging from $29 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Winchester is $150 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Winchester home is $25. Wondering if you can bring your dog or cat along with you? There are 7 pet-friendly vacation rentals available in Winchester. In addition to accommodating pets, Winchester rentals offer a variety of amenities. In particular, 28 rentals have Internet and WiFi, 20 have TV and/or cable and 6 have a pool or hot tub. Search properties from 5 vacation rental sites in Winchester where the top providers in that area are HomeAway, TripAdvisor, and HRS Holidays. There are 19 HomeAway rentals, 7 TripAdvisor short term rentals and 4 HRS Holidays vacation rentals.

Popular Day Trips Near Winchester

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