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Compare 349 Vacation Homes in Pittsfield with updated reviews, rates, and availability.
Private Lake House in the Berkshires
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, 15 reviews
Hearts Desire is a furnished whole house in a small, colorful garden center.
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, 66 reviews
3 Bedroom Lakefront Home with Hot Tub & Fireplace
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, 97 reviews
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Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
9.6 out of 10, Exceptional, 9 reviews
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, 11 reviews
The price is $800
$1,340 total
includes taxes & fees
Jun 10 - Jun 11
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
9.4 out of 10, Exceptional, 3 reviews
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, 117 reviews
Tranquil 3-BR Waterfront Retreat
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, 7 reviews
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, 3 reviews
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
10.0 out of 10, Exceptional, 93 reviews
Private Cabin On Over 12 Acres Of Woods!
Private Cabin On Over 12 Acres Of Woods!
10.0 out of 10, Exceptional, 3 reviews
The price is $824
$1,419 total
includes taxes & fees
Jul 6 - Jul 7
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, 106 reviews
Historic New Lebanon Hideaway on 33 Private Acres!
Historic New Lebanon Hideaway on 33 Private Acres!
10.0 out of 10, Exceptional, 1 review
Berkshire Manor for Lasting Memories
Berkshire Manor for Lasting Memories
10.0 out of 10, Exceptional, 2 reviews
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
Berkshires sanctuary w/ outdoor living area & fire pit. Minutes from Tanglewood!
The price is $360
$765 total
includes taxes & fees
Jun 10 - Jun 11
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, 8 reviews
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, 12 reviews
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, 20 reviews
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Pittsfield
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, 4 reviews
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, 859 reviews
The price is $146
$161 total
includes taxes & fees
Jun 24 - Jun 25
Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, 1,676 reviews
The price is $169
$195 total
includes taxes & fees
Jun 9 - Jun 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Pittsfield Vacation Homes information
Number of reviews | 735 |
---|---|
Accommodation | 349 Vacation Homes |
Lowest Price | $360 |
Highest Price | $824 |
Recent reviews of Pittsfield hotelsExpedia verified reviews
5/5 Excellent
"Like the atmosphere and the service provided at the front desk "
A verified traveler stayed at Life House Berkshires
Posted 2 days ago
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