Find Vacation Rentals in Winchester

We have 435 properties to choose from
Anytime
1 guest
Anytime
1 guest

Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

Apartment Winchester
from $89 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(3 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Farmhouse Winchester
from $133 per night
Farmhouse ∙ 4 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $173 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(51 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Condo Winchester
from $286 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(28 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $226 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(101 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $162 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(10 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $203 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding(12 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $96 per night
Apartment ∙ 3 guests ∙ 1 bedroom
5.0
Outstanding(12 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $133 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.8
Outstanding(13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
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Recommended Rentals With Pools

Apartment  Winchester
from $182 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(9 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Vrbo
Details
Aparthotel  Winchester
from $222 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom
4.5
Excellent(944 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
HomeToGo
Details
House  Winchester
from $467 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding(11 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

Apartment  Winchester
from $133 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
4.8
Outstanding(13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Winchester
from $254 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding(1 rating)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Winchester
from $444 per night
House ∙ 9 guests ∙ 4 bedrooms
5.0
Outstanding(4 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
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Best vacation rentals with a balcony

House  Winchester
from $173 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent(72 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Vrbo
Details
House  Winchester
from $381 per night
House ∙ 11 guests ∙ 5 bedrooms
5.0
Outstanding(15 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Vrbo
Details
Condo  Winchester
from $371 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding(64 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Vrbo
Details
Show more

Frequently Asked Questions

Is renting a vacation home in Winchester expensive?

Usually, a stay in Winchester starts at $89 per night.

Are there any vacation rentals available to book in Winchester?

On tripping.com, you will find 435 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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