Find Vacation Rentals in Winchester

Winchester
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

Aparthotel Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$124 per night
Aparthotel ∙ 3 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 3/19 - 3/26 (Sat - Sat)
$189 per night
Aparthotel ∙ 3 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$126 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$126 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$113 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 3/19 - 3/26 (Sat - Sat)
$199 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 1/21 - 1/28 (Fri - Fri)
$134 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 3/19 - 3/26 (Sat - Sat)
$199 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
Details
Aparthotel Winchester
e.g. 1/21 - 1/28 (Fri - Fri)
$134 per night
Aparthotel ∙ 5 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Details
HomeToGo
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Recommended Rentals With Pools

Aparthotel Pool Winchester
e.g. 1/17 - 1/24 (Mon - Mon)
-6%
$148
$139 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (4995 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
Hyatt.com
Details
Aparthotel Pool Winchester
e.g. 3/19 - 3/26 (Sat - Sat)
$120 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
HomeToGo
Details
Aparthotel Pool Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$126 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pool
Details
HomeToGo
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Pet-Friendly Homes and Apartments

Aparthotel Pet-friendly Winchester
e.g. 1/17 - 1/24 (Mon - Mon)
-28%
$104
$75 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.0
"Very good" (2502 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
FindHotel
Details
Aparthotel Pet-friendly Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$124 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
HomeToGo
Details
Aparthotel Pet-friendly Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$124 per night
Aparthotel ∙ 3 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Details
HomeToGo
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Vacation Homes With Terraces

Aparthotel Balcony/Patio Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$124 per night
Aparthotel ∙ 2 guests ∙ 1 bedroom
4.5
"Outstanding" (1520 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony/Patio
Details
Homewood Suites
Details
Aparthotel Balcony/Patio Winchester
e.g. 2/5 - 2/12 (Sat - Sat)
$181 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Balcony/Patio
Details
HomeToGo
Details
Aparthotel Balcony/Patio Winchester
e.g. 1/21 - 1/28 (Fri - Fri)
$134 per night
Aparthotel ∙ 5 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Balcony/Patio
Details
HomeToGo
Details
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Frequently Asked Questions

Is renting a vacation home in Winchester expensive?

Usually, a stay in Winchester starts at $104 per night.

Are there any vacation rentals available to book in Winchester?

On tripping.com, you will find 15 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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