Vacation Rentals in Pittsfield (MA)

Vacation Rentals in Pittsfield (MA)

Start comparing over 26 rentals in Pittsfield (MA) and book at the best price!

Find Vacation Rentals in Pittsfield (MA)

Best Vacation Rentals in Pittsfield (MA)

Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation Rental for 4 Guests in Pittsfield (ma), Berkshire County
Vacation Rental for 4 Guests in Pittsfield (ma), Berkshire County, Picture 1
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Pittsfield (ma), Berkshire County
Vacation Rental • 990 ft² • 2 Bedrooms
9.7
(37 reviews)
Comfortable, quiet home in Pittsfield minutes from Tanglewood, Berkshire Theater Festivals and other year round attractions. Oldest one room school house in New England and listed as a U.S. National Historic Place. Built in 1825 and rebuilt 1843 after a fire. Morewood has been used continually by the community until being converted to a private residence in 1985. The home was completely renovated in 2010 with glass and tile bathroom and updates throughout the 1000 square foot interior located in the middle of an acre wooded lot on a quiet mountain road. The bedroom with a queen sized bed is...
from $294 / night
Vacation Rental for 25 Guests in Pittsfield (ma), Berkshire County
Vacation Rental for 25 Guests in Pittsfield (ma), Berkshire County, Picture 1
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Vacation Rental for 25 Guests in Pittsfield (ma), Berkshire County, Picture 3
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Pittsfield (ma), Berkshire County
Vacation Rental • 3993 ft² • 8 Bedrooms
9.7
(63 reviews)
Welcome.....we invite you to come enjoy the great space of our beautiful home with your family and friends in our unique 4000 sq. ft. custom built home with sleeping accommodations for up to 25. With 8 bedrooms, 2 full kitchens, 3 bathrooms and great outdoor space for relaxing and entertaining, we think it's the perfect gathering spot. The house is nestled in the heart of the Berkshire Mountains and situated between 2 beautiful lakes that have incredible views. One lake (Onota) is just a short walk down the street where you can enjoy swimming, boating, fishing, picnicking and more. Feel fre...
from $378 / night
Vacation Rental for 10 Guests in Pittsfield (ma), Berkshire County
Vacation Rental for 10 Guests in Pittsfield (ma), Berkshire County, Picture 1
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Vacation Rental for 10 Guests in Pittsfield (ma), Berkshire County, Picture 3
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Pittsfield (ma), Berkshire County
Vacation Rental • 1798 ft² • 3 Bedrooms
9.4
(33 reviews)
Our 3 bedroom, 2 bath home has a huge 3 season sun room on the second floor with an even bigger covered deck below. The main floor has the kitchen, two bedrooms, living room, the sun room and a bath. The lower floor has a huge family room with two sets of sliders onto the deck plus another bedroom and a full bath with clothes washer and dryer. The property also features a large, deep water dock for your boat. Weekly rentals are Saturday to Saturday.This house is located on beautiful Onota Lake, in the heart of the Berkshires. Great for water sports, kayaking, fishing, or just watching the s...
from $386 / night

Prices and availability

Current Vacation rental prices Pittsfield (MA)

$459for 29 Jun - 6 Jul
$359 annual average
Jul
Aug
Sep
Oct
Average price per week

Current vacation rental availability Pittsfield (MA)

6%for 29 Jun - 6 Jul
11% annual average
Jul
Aug
Sep
Oct
Percentage of available rentals

FAQs: Vacation Rentals in Pittsfield (MA)

How much does it cost to book a vacation rental in Pittsfield?

We can see from last year that Pittsfield had an average price of $261 per night, a relatively high one for a city in the USA.

Which months allow you to save the most on vacation rentals?

If you want to save the maximum during your vacation to Pittsfield, go there in February ($177 per night on average), March ($189), or May ($210), to find the lowest prices for the whole year.

During which months are vacation rentals more expensive in Pittsfield?

Analyzing the data from last year, we found that costs per night for accommodation here are usually higher, on average, during the months of September ($331), July ($324), and January ($317).

Is it necessary to plan a trip to Pittsfield well in advance?

If you decide to put Pittsfield on your bucket list, we suggest planning your visit long before you go because it is usually very high in demand, with an annual average of 88% of rentals booked the previous year.

What time of the year can I find more available vacation rentals?

The most available months are, on average, September (with an availability of 46%), December (27%), and January (18%), according to the trends observed in the prior year.

How many vacation rentals does Holidu have in Pittsfield?

We have 70 properties for you in Pittsfield, provided by our 2 local and international partners.

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