The Best Airbnb Deals in
Pittsfield, Massachusetts

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Pittsfield, Massachusetts. Enter your travel dates to find the best deals!

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AirDNA Score: 81
$245/night

Exquisite Apartment in Grand Victorian Home 1

2 beds
1 bath
4 guests
Average Price:  
$265
8% Cheaper
than normal
AirDNA Score: 80
$450/night

Grand Colonial Home in the Heart of The Berkshires

4 beds
2.5 baths
12 guests
Average Price:  
$558
19% Cheaper
than normal
AirDNA Score: 79
$165/night

Heart Of The Berkshires

3 beds
1 bath
5 guests
Average Price:  
$205
20% Cheaper
than normal
AirDNA Score: 69
$165/night

The Lakehouse

2 beds
1 bath
7 guests
Average Price:  
$173
5% Cheaper
than normal
AirDNA Score: 66
$750/night

Willowbrook: A Sun Filled, Mid-century Modern Home

7 beds
4.5 baths
14 guests
Average Price:  
$831
10% Cheaper
than normal
AirDNA Score: 57
$99/night

Honeysuckle Rose Cottage

2 beds
1 bath
4 guests
Average Price:  
$123
20% Cheaper
than normal
AirDNA Score: 53
$289/night

The Oliver Wendell Holmes Guesthouse @ Holmesdale

1 bed
1 bath
4 guests
Average Price:  
$445
35% Cheaper
than normal
AirDNA Score: 51
$99/night

Hillcrest House: Your Bright and Spacious 3 BR!

3 beds
1.5 baths
6 guests
Average Price:  
$126
21% Cheaper
than normal
AirDNA Score: 51
$189/night

One Bedroom Apartment with a full kitchen

1 bed
1 bath
4 guests
Average Price:  
$158
20% More
than normal
AirDNA Score: 44
$245/night

Exquisite Apartment in Grand Victorian 2

2 beds
1 bath
4 guests
Average Price:  
$289
15% Cheaper
than normal
AirDNA Score: 29
$276/night

Bartlett Victorian Unit 1

3 beds
1.5 baths
6 guests
Average Price:  
$289
4% Cheaper
than normal
AirDNA Score: 21
$107/night

Dancing Horse Lodge

3 beds
1 bath
6 guests
Average Price:  
$135
21% Cheaper
than normal