Find Vacation Rentals in Pittsfield

We have 51 properties to choose from
Pittsfield
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Pittsfield
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
$1,358 per night
House ∙ 30 guests ∙ 14 bedrooms
4.0
Very good (1 rating)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$353 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (28 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$330 per night
House ∙ 11 guests ∙ 4 bedrooms
4.9
Outstanding (32 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$300 per night
House ∙ 10 guests ∙ 3 bedrooms
4.3
Very good (18 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$769 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (34 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$1,047 per night
House ∙ 23 guests ∙ 9 bedrooms
5.0
Outstanding (47 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$157 per night
House ∙ 14 guests ∙ 5 bedrooms
4.7
Excellent (57 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$375 per night
House ∙ 8 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
HomeToGo
Details
Details
House Pittsfield
$638 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
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Recommended Rentals With Pools

Condo  Pittsfield
$211 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (16 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Details
Vrbo
Details
Details
Condo  Pittsfield
-11%
$181
$161 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.2
Very good (16 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Details
Vacasa
Details
Details
Condo  Pittsfield
$181 per night
Condo ∙ 6 guests ∙ 2 bedrooms
4.2
Very good (16 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Details
Vrbo
Details
Details
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Pet-Friendly Homes and Apartments

House  Pittsfield
$310 per night
House ∙ 8 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
HomeToGo
Details
Details
House  Pittsfield
$435 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (25 ratings)
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
Vrbo
Details
Details
House  Pittsfield
$230 per night
House ∙ 15 guests ∙ 3 bedrooms
4.9
Outstanding (121 ratings)
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
Vrbo
Details
Details
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Best vacation rentals with a balcony

House  Pittsfield
$286 per night
House ∙ 10 guests ∙ 3 bedrooms
4.3
Very good (18 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony
Details
Vacasa
Details
Details
House  Pittsfield
$297 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (28 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony
Details
Vrbo
Details
Details
House  Pittsfield
$414 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony
Details
Vrbo
Details
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Pittsfield on average?

Prices for a stay in Pittsfield begin at $149 per night.

Are there any vacation rentals available to book in Pittsfield?

There are 51 vacation rental offers in Pittsfield available to book.

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 Pittsfield

Find the best Pittsfield vacation rentals on Tripping.com. With over 41 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Pittsfield range from $65 a night. Many rentals can also be booked directly online. Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 37 homes in Pittsfield offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 0 rentals with pool or jacuzzi, or relax with the family in one of the 39 homes with cable TV. For all those pet owners with dogs or cats, Pittsfield offers 14 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com. Search properties from 6 vacation rental sites in Pittsfield where the top providers in that area are HomeAway, Expedia, and RedAwning. There are 23 HomeAway rentals, 6 Expedia short term rentals and 4 RedAwning vacation rentals.

Popular Day Trips Near Pittsfield

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