Find Vacation Rentals in Winchester

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Winchester
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Winchester
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

Condo Winchester
$149 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (16 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$387 per night
House ∙ 8 guests ∙ 4 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Aparthotel Winchester
$214 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom
4.6
Excellent (2154 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Details
Apartment Winchester
$91 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Apartment Winchester
$88 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (7 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Condo Winchester
$150 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (4 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$209 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding (94 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$136 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (4 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$203 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (3 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Winchester
$233 per night
House ∙ 6 guests ∙ 4 bedrooms
5.0
Outstanding (8 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Winchester
$275 per night
House ∙ 6 guests ∙ 3 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
Apartment  Winchester
$227 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
Vrbo
Details
Details
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Best vacation rentals with a balcony

Apartment  Winchester
$306 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
House  Winchester
$181 per night
House ∙ 6 guests ∙ 2 bedrooms
4.7
Excellent (68 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
House  Winchester
$251 per night
House ∙ 8 guests ∙ 4 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
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Recommended Rentals With Pools

Aparthotel  Winchester
$156 per night
Aparthotel ∙ 8 guests ∙ 1 bedroom
4.6
Excellent (2197 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
Expedia
Details
Details
Aparthotel  Winchester
$258 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom
4.6
Excellent (2154 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
HomeToGo
Details
Details
Aparthotel  Winchester
$283 per night
Aparthotel ∙ 8 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
Vrbo
Details
Details
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Frequently Asked Questions

Is renting a vacation home in Winchester expensive?

Usually, a stay in Winchester starts at $88 per night.

Are there any vacation rentals available to book in Winchester?

On tripping.com, you will find 390 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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