Find Vacation Rentals in Pittsfield

We have 48 properties to choose from
Pittsfield
Anytime
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
$510 per night
House ∙ 10 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
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House Pittsfield
$546 per night
House ∙ 10 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
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Vrbo
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House Pittsfield
$795 per night
House ∙ 11 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
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HomeToGo
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House Pittsfield
$500 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding (43 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
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Details
House Pittsfield
$462 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9
Outstanding (28 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
Details
Details
House Pittsfield
$443 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (24 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
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Cabin Pittsfield
$835 per night
Cabin ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (1 rating)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
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House Pittsfield
$508 per night
House ∙ 12 guests ∙ 3 bedrooms
4.7
Excellent (59 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
HomeToGo
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Details
House Pittsfield
$361 per night
House ∙ 10 guests ∙ 3 bedrooms
4.3
Very good (18 ratings)
Pittsfield, Rutland County, Vermont, United States
Details
Vrbo
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Recommended Rentals With Pools

Condo  Pittsfield
$162 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
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Vrbo
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Details
House  Pittsfield
$744 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding (78 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Details
Vrbo
Details
Details
Condo  Pittsfield
$188 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (16 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
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Vrbo
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Vacation Homes With Terraces

House  Pittsfield
$1,010 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (2 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Pittsfield
$302 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (115 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony/Patio
Details
Vrbo
Details
Details
House  Pittsfield
$177 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (10 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony/Patio
Details
Vrbo
Details
Details
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Vacation homes and rentals with a yard

House  Pittsfield
$1,005 per night
House ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding (70 ratings)
Pittsfield, Rutland County, Vermont, United States
Yard
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Vrbo
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Details
House  Pittsfield
$354 per night
House ∙ 21 guests ∙ 5 bedrooms
4.5
Excellent (26 ratings)
Pittsfield, Rutland County, Vermont, United States
Yard
Details
Vrbo
Details
Details
House  Pittsfield
$1,478 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding (59 ratings)
Pittsfield, Rutland County, Vermont, United States
Yard
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 $114 per night.

Are there any vacation rentals available to book in Pittsfield?

There are 49 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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