Find Vacation Rentals in Winchester

We have 465 properties to choose from
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Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

Apartment Winchester
from $96 per night
4 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(3 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Farmhouse Winchester
from $131 per night
4 guests ∙ 2 bedrooms

Farmhouse

Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $157 per night
Apartment ∙ 4 guests ∙ 1 bedroom

84 m² Apartment

5.0
Outstanding(51 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Condo Winchester
from $203 per night
6 guests ∙ 3 bedrooms

Condo

5.0
Outstanding(28 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $195 per night
7 guests ∙ 3 bedrooms

House

5.0
Outstanding(101 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $217 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(10 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $96 per night
3 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(12 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
Apartment Winchester
from $117 per night
5 guests ∙ 2 bedrooms

Apartment

4.8
Outstanding(13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
House Winchester
from $408 per night
11 guests ∙ 5 bedrooms

House

5.0
Outstanding(15 ratings)
Winchester, Middlesex County, Massachusetts, United States
Vrbo
Details
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Recommended Rentals With Pools

Apartment  Winchester
from $195 per night
Apartment ∙ 5 guests ∙ 2 bedrooms

186 m² Apartment

5.0
Outstanding(9 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
Vrbo
Details
Aparthotel  Winchester
from $239 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom

69 m² Aparthotel

4.5
Excellent(944 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pool
HomeToGo
Details
House  Winchester
from $407 per night
House ∙ 8 guests ∙ 4 bedrooms

186 m² House

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 $117 per night
5 guests ∙ 2 bedrooms

Apartment

4.8
Outstanding(13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Winchester
from $407 per night
6 guests ∙ 3 bedrooms

House

5.0
Outstanding(1 rating)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Winchester
from $354 per night
9 guests ∙ 4 bedrooms

House

5.0
Outstanding(4 ratings)
Winchester, Middlesex County, Massachusetts, United States
Pet-friendly
Vrbo
Details
Show more

Vacation rentals with a balcony

House  Winchester
from $210 per night
House ∙ 6 guests ∙ 3 bedrooms

125 m² House

4.7
Excellent(72 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Vrbo
Details
House  Winchester
from $408 per night
11 guests ∙ 5 bedrooms

House

5.0
Outstanding(15 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Vrbo
Details
Condo  Winchester
from $351 per night
Condo ∙ 8 guests ∙ 3 bedrooms

173 m² Condo

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 $94 per night.

Are there any vacation rentals available to book in Winchester?

On tripping.com, you will find 465 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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