Find Vacation Rentals in Winchester

We have 15 properties to choose from
Winchester
Anytime
Guests

Popular Winchester Vacation Rentals

Find the perfect Winchester vacation rental

House Winchester
$203 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Apartment Winchester
$179 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Condo Winchester
$131 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$144 per night
House ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (21 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Condo Winchester
$178 per night
Condo ∙ 5 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$211 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
"Excellent" (53 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$189 per night
House ∙ 6 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
House Winchester
$140 per night
House ∙ 6 guests ∙ 2 bedrooms
4.7
"Outstanding" (70 ratings)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
Condo Winchester
$166 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Details
Vrbo
Details
Details
View more

Vacation rentals and apartments with air conditioning

House Aircondition Winchester
$463 per night
House ∙ 2 guests ∙ 4 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Aircondition
Details
Vrbo
Details
Details
House Aircondition Winchester
$137 per night
House ∙ 4 guests ∙ 1 bedroom
Winchester, Middlesex County, Massachusetts, United States
Aircondition
Details
Vrbo
Details
Details
Condo Aircondition Winchester
$249 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Aircondition
Details
Vrbo
Details
Details
View more

Best vacation rentals with a balcony

Condo Balcony Winchester
$316 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (43 ratings)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
Condo Balcony Winchester
$266 per night
Condo ∙ 6 guests ∙ 3 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Vrbo
Details
Details
Condo Balcony Winchester
$170 per night
Condo ∙ 8 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Balcony
Details
Expedia
Details
Details
View more

Vacation homes and rentals with a yard

House Yard Winchester
$289 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
"Excellent" (1 rating)
Winchester, Middlesex County, Massachusetts, United States
Yard
Details
Vrbo
Details
Details
Apartment Yard Winchester
$323 per night
Apartment ∙ 4 guests ∙ 1 bedroom
3.7
"Good" (13 ratings)
Winchester, Middlesex County, Massachusetts, United States
Yard
Details
Vrbo
Details
Details
House Yard Winchester
$378 per night
House ∙ 3 guests ∙ 2 bedrooms
Winchester, Middlesex County, Massachusetts, United States
Yard
Details
Vrbo
Details
Details
View more

Frequently Asked Questions

Is renting a vacation home in Winchester expensive?

Usually, a stay in Winchester starts at $127 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

image-tag