Vacation Rentals in Pittsfield (MA)

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

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8.0

Vacation Rentals in Pittsfield (MA)

Vacation rental for 4 people, with balcony

2 bedrooms

10.0

(5 reviews)

from $78 / nightFREE cancellation

Vacation rental for 5 people, with yard

2 bedrooms

10.0

(10 reviews)

from $199 / nightFREE cancellation

Vacation rental for 6 people, with yard, with pets

3 bedrooms

9.2

(23 reviews)

from $143 / nightFREE cancellation

Vacation rental for 4 people, with yard, with pets

2 bedrooms

9.7

(37 reviews)

from $310 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 7 people, with yard and terrace

4 bedrooms

10.0

(3 reviews)

from $291 / nightFREE cancellation

Vacation rental for 5 people, with terrace and yard

3 bedrooms

9.9

(19 reviews)

from $218 / nightFREE cancellation

Vacation rental for 8 people, with pool, with pets

4 bedrooms

from $541 / nightFREE cancellation

Vacation rental for 10 people, with yard, with pets

5 bedrooms

8.8

(8 reviews)

from $162 / nightFREE cancellation

Vacation rentals with hot tub

Hot tub

Vacation rental for 10 people, with balcony and yard as well as hot tub

4 bedrooms

9.8

(42 reviews)

from $554 / nightFREE cancellation

Hot tub

Vacation rental for 9 people, with hot tub and sauna as well as yard

5 bedrooms

10.0

(11 reviews)

from $1,704 / nightFREE cancellation

Hot tub

Vacation rental for 10 people, with yard and hot tub, with pets

5 bedrooms

10.0

(4 reviews)

from $477 / nightFREE cancellation

Hot tub

Vacation rental for 25 people, with yard and hot tub, with pets

8 bedrooms

9.7

(63 reviews)

from $395 / nightFREE cancellation

Vacation Rentals with Yard

Yard

Vacation rental for 10 people, with yard and balcony

5 bedrooms

9.9

(48 reviews)

from $603 / nightFREE cancellation

Yard

Vacation rental for 8 people, with yard and terrace

3 bedrooms

10.0

(22 reviews)

from $270 / nightFREE cancellation

Yard

Vacation rental for 12 people, with yard and terrace

4 bedrooms

9.8

(22 reviews)

from $462 / nightFREE cancellation

Yard

Vacation rental for 16 people, with yard

6 bedrooms

10.0

(28 reviews)

from $744 / nightFREE cancellation

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 10 Guests in Pittsfield (ma), Berkshire County

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Pittsfield (ma), Berkshire County

Vacation Rental • 1798 ft² • 3 Bedrooms

Pittsfield (ma), Berkshire County

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 $289 / night

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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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Pittsfield (ma), Berkshire County

Vacation Rental • 3993 ft² • 8 Bedrooms

Pittsfield (ma), Berkshire County

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 $395 / night

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Vacation Rental for 9 Guests in Pittsfield (ma), Berkshire County

Vacation Rental for 9 Guests in Pittsfield (ma), Berkshire County, Picture 1

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Pittsfield (ma), Berkshire County

Vacation Rental • 7395 ft² • 5 Bedrooms

Pittsfield (ma), Berkshire County

10.0

(11 reviews)

Fox Hollow, a private 1940s estate home, renovated to modern-day luxury, located in gorgeous Berkshire County, is a 3-level home with 7,800 sq feet of living space, situated on 21 acres; including 5 acres of rolling lawn and 16 acres of forest.This gorgeous, historic home built by the prominent Samuel Colt family in 1940, has been newly renovated and has 5 bedrooms, 3 full baths and 2 half baths, top of the line Subzero / Wolf appliances, and state of the art technology throughout. Situated just 5 minutes from downtown Pittsfield, MA, within close proximity to Onota Lake, Lake Pontoosic, Ta...

from $1,704 / night

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Prices and availability

Current Vacation rental prices Pittsfield (MA)

$334for 27 Apr - 4 May

$316 annual average

Jun

Jul

Aug

Oct

Average price per week

Current vacation rental availability Pittsfield (MA)

58%for 27 Apr - 4 May

21% annual average

Jun

Jul

Aug

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.