Find Vacation Rentals in Pittsfield

We have 102 properties to choose from
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
from $359 per night
6 guests ∙ 3 bedrooms

House

4.9
Outstanding(32 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $923 per night
30 guests ∙ 14 bedrooms

House

3.4
(5 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $1,035 per night
House ∙ 23 guests ∙ 9 bedrooms

557 m² House

5.0
Outstanding(48 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $240 per night
House ∙ 15 guests ∙ 5 bedrooms

186 m² House

4.9
Outstanding(128 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $641 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(4 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $325 per night
House ∙ 12 guests ∙ 5 bedrooms

232 m² House

5.0
Outstanding(45 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $587 per night
House ∙ 10 guests ∙ 3 bedrooms

260 m² House

Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $165 per night
14 guests ∙ 6 bedrooms

House

4.7
Excellent(52 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
House Pittsfield
from $333 per night
House ∙ 11 guests ∙ 5 bedrooms

149 m² House

4.7
Excellent(56 ratings)
Pittsfield, Rutland County, Vermont, United States
Vrbo
Details
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Recommended Rentals With Pools

Condo  Pittsfield
from $394 per night
6 guests ∙ 3 bedrooms

Condo

4.4
Very good(36 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Vrbo
Details
Condo  Pittsfield
from $278 per night
6 guests ∙ 3 bedrooms

Condo

4.5
Excellent(33 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Vrbo
Details
Condo  Pittsfield
from $204 per night
Condo ∙ 6 guests ∙ 3 bedrooms

139 m² Condo

5.0
Outstanding(2 ratings)
Pittsfield, Rutland County, Vermont, United States
Pool
Vrbo
Details
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Pet-Friendly Homes and Apartments

House  Pittsfield
from $379 per night
House ∙ 10 guests ∙ 3 bedrooms

167 m² House

Pittsfield, Rutland County, Vermont, United States
Pet-friendly
HomeToGo
Details
House  Pittsfield
from $401 per night
6 guests ∙ 3 bedrooms

House

Pittsfield, Rutland County, Vermont, United States
Pet-friendly
HomeToGo
Details
House  Pittsfield
from $704 per night
House ∙ 8 guests ∙ 3 bedrooms

139 m² House

Pittsfield, Rutland County, Vermont, United States
Pet-friendly
Vrbo
Details
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Accommodations With Saunas

House  Pittsfield
from $352 per night
House ∙ 8 guests ∙ 3 bedrooms

117 m² House

Pittsfield, Rutland County, Vermont, United States
Sauna
HomeToGo
Details
House  Pittsfield
from $424 per night
House ∙ 8 guests ∙ 3 bedrooms

237 m² House

4.8
Outstanding(19 ratings)
Pittsfield, Rutland County, Vermont, United States
Sauna
HomeToGo
Details
House  Pittsfield
from $380 per night
House ∙ 8 guests ∙ 3 bedrooms

237 m² House

4.8
Outstanding(19 ratings)
Pittsfield, Rutland County, Vermont, United States
Sauna
Vrbo
Details
Show more

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 $175 per night.

Are there any vacation rentals available to book in Pittsfield?

There are 96 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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