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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

Apartment Pittsfield
e.g. 9/1 - 9/8 (Thu - Thu)
$611 per night
Apartment ∙ 10 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
HomeToGo
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House Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-75%
$1,326
$326 per night
House ∙ 12 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
Expedia
Details
Condo Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-72%
$1,152
$326 per night
Condo ∙ 11 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
Expedia
Details
House Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-71%
$1,331
$389 per night
House ∙ 10 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Free cancellation
Details
TripAdvisor
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House Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-70%
$1,235
$374 per night
House ∙ 11 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
Free cancellation
Details
TripAdvisor
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House Pittsfield
e.g. 12/11 - 12/18 (Sat - Sat)
$492 per night
House ∙ 11 guests ∙ 5 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
TripAdvisor
Details
House Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-65%
$1,063
$374 per night
House ∙ 12 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Details
TripAdvisor
Details
House Pittsfield
e.g. 11/13 - 11/20 (Sat - Sat)
-62%
$1,440
$541 per night
House ∙ 12 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
Free cancellation
Details
TripAdvisor
Details
Condo Pittsfield
e.g. 10/11 - 10/18 (Mon - Mon)
-77%
$567
$129 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pittsfield, Rutland County, Vermont, United States
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HomeToGo
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Recommended Rentals With Pools

Condo Pool Pittsfield
e.g. 9/24 - 10/1 (Fri - Fri)
-82%
$698
$129 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pittsfield, Rutland County, Vermont, United States
Pool
Details
HomeToGo
Details
Condo Pool Pittsfield
e.g. 10/12 - 10/19 (Tue - Tue)
$200 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pittsfield, Rutland County, Vermont, United States
Pool
Details
HomeToGo
Details
Condo Pool Pittsfield
e.g. 10/11 - 10/18 (Mon - Mon)
-78%
$843
$183 per night
Condo ∙ 4 guests ∙ 1 bedroom
Pittsfield, Rutland County, Vermont, United States
Pool
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HomeToGo
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Pet-Friendly Homes and Apartments

House Pet-friendly Pittsfield
e.g. 10/12 - 10/19 (Tue - Tue)
-66%
$1,555
$529 per night
House ∙ 12 guests ∙ 3 bedrooms
4.6/5.0 "Outstanding"
(28 ratings)
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
HomeToGo
Details
House Pet-friendly Pittsfield
e.g. 10/12 - 10/19 (Tue - Tue)
-68%
$1,326
$418 per night
House ∙ 12 guests ∙ 3 bedrooms
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
Expedia
Details
Condo Pet-friendly Pittsfield
e.g. 9/18 - 9/25 (Sat - Sat)
$340 per night
Condo ∙ 11 guests ∙ 4 bedrooms
Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Details
HomeToGo
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Best vacation rentals with a balcony

House Balcony Pittsfield
e.g. 9/18 - 9/25 (Sat - Sat)
-72%
$2,199
$615 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0/5.0 "Excellent"
(9 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony
Details
HomeToGo
Details
House Balcony Pittsfield
e.g. 9/18 - 9/25 (Sat - Sat)
-72%
$1,537
$432 per night
House ∙ 11 guests ∙ 4 bedrooms
4.9/5.0 "Excellent"
(18 ratings)
Pittsfield, Rutland County, Vermont, United States
Balcony
Details
HomeToGo
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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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