Pittsfield Cottages
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Featured Cottages in Pittsfield
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Stay at this vacation home in Pittsfield. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Jiminy Peak Mountain Resort and Crane Museum of Papermaking are located nearby.
Kitchen
Pet-friendly
Charming historic cottage on scenic road to Mt. Greylock
Stay at this cottage in Lanesborough. Enjoy free WiFi, a garden, and Netflix. Popular attractions Jiminy Peak Mountain Resort and Mount Greylock State Reservation Visitor Center are located nearby.
Kitchen
Free WiFi
Cozy Berkshire cottage with fireplace.
Stay at this cottage in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Bousquet Ski Area are located nearby.
Kitchen
Washer
Lake Views & Dock Access - Pittsfield Cottage!
Stay at this cottage in Pittsfield. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Jiminy Peak Mountain Resort and Crane Museum of Papermaking are located nearby.
Kitchen
Washer
Beachwood Cottage
Stay at this cottage in West Stockbridge. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and Stockbridge Bowl are located nearby.
Kitchen
Washer
Heaven Cant Wait, On Beautiful Kinderhook
Stay at this cottage in Valatie. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Kinderhook Lake and Valatie Free Library are located nearby.
Kitchen
Pet-friendly
Private Island - Largest Fresh Water Reservoir in Mass....
Stay at this cottage in Otis. Enjoy free WiFi, a garden, and patios. Popular attractions Larkum Pond and Otis Reservoir are located nearby.
Kitchen
Pet-friendly
Grandparent’s Cottage 250 steps to the lake
Stay at this vacation home in West Stockbridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tanglewood Music Center and Stockbridge Bowl are located nearby.
Kitchen
Washer
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Stay at this cottage in Great Barrington. Enjoy laundry facilities, patios, and in-room washers/dryers. Popular attractions Lake Buel and Les Trois Emme Winery are located nearby.
Kitchen
Washer
Quiet rustic cottage with shared lake access
Book a stay at this family-friendly cottage in Great Barrington. Enjoy a garden, laundry facilities, and patios. Popular attractions Lake Buel and Les Trois Emme Winery are located nearby.
Washer
Dryer
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.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.
^Eligibility requirements and conditions apply.
Pittsfield Cottages essential information
Accommodation | 109 Cottages |
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Lowest Price | |
Highest Price | |
Popular accommodation | Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location, Charming historic cottage on scenic road to Mt. Greylock, Cozy Berkshire cottage with fireplace., Lake Views & Dock Access - Pittsfield Cottage!, Beachwood Cottage, Heaven Cant Wait, On Beautiful Kinderhook, Private Island - Largest Fresh Water Reservoir in Mass...., Grandparent’s Cottage 250 steps to the lake, Rustic Berkshires Cottage at Lake Buel w/ Kayaks!, Quiet rustic cottage with shared lake access, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! |
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More accommodations in Pittsfield
Top trending hotels in Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
8.4/10 Very Good! (1,001 reviews)
^Eligibility requirements and conditions apply