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Explore Gay Accommodations in Pittsfield

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WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
LGBTQ Flaglock
Howard
Entire place • 7.7 miles from Pittsfield
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone...
Hot tub • Parking • Air conditioning
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
LGBTQ Flaglock
Howard
Entire place • 7.7 miles from Pittsfield
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hot tub • Parking • Air conditioning
Friendly
The Cascades
The Cascades
The Cascades
The Cascades
The Cascades
Approval 
Instant
Hotel room ** • 7.7 miles from Pittsfield
★ 4.52 (1)
The Cascades
🏆 Pride Points x3
Wi-Fi • Parking • Pets allowed
Friendly
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
Approval 
Instant
Entire place • 7.7 miles from Pittsfield
★ 4.96 (1)
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
🏆 Pride Points x3
Wi-Fi • Pool • Hot tub
Friendly
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Approval 
Instant
Hotel room *** • 7.7 miles from Pittsfield
★ 4.6 (1)
Jiminy Peak Mountain Resort
🏆 Pride Points x3
Wi-Fi • Pool • Hot tub
Friendly
Mountainside Condo @ Jiminy Peak in the Berkshires
Mountainside Condo @ Jiminy Peak in the Berkshires
Mountainside Condo @ Jiminy Peak in the Berkshires
Mountainside Condo @ Jiminy Peak in the Berkshires
Mountainside Condo @ Jiminy Peak in the Berkshires
Approval 
Instant
Entire place • 7.8 miles from Pittsfield
★ 5 (1)
Mountainside Condo @ Jiminy Peak in the Berkshires
🏆 Pride Points x3
Pool • Hot tub • Parking
Friendly
Berkshire Hideaway with Fire Pit and Playground!
Berkshire Hideaway with Fire Pit and Playground!
Berkshire Hideaway with Fire Pit and Playground!
Berkshire Hideaway with Fire Pit and Playground!
Berkshire Hideaway with Fire Pit and Playground!
Approval 
Instant
Entire place • 7.9 miles from Pittsfield
Berkshire Hideaway with Fire Pit and Playground!
🏆 Pride Points x3
Wi-Fi • Parking
*** Your Own B&B***
*** Your Own B&B***
*** Your Own B&B***
*** Your Own B&B***
*** Your Own B&B***
LGBTQ Flag
Benjamin
Entire place • 8.2 miles from Pittsfield
*** Your Own B&B***
Hot tub • Parking • Pets allowed
Friendly
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Vacation Village in the Berkshires
Approval 
Instant
Hotel room ***** • 8.2 miles from Pittsfield
★ 4.8 (1)
Vacation Village in the Berkshires
🏆 Pride Points x3
Wi-Fi • Pool • Hot tub
Friendly
Autumn Hill Lakehouse
Autumn Hill Lakehouse
Autumn Hill Lakehouse
Autumn Hill Lakehouse
Autumn Hill Lakehouse
Approval 
Instant
Entire place • 8.3 miles from Pittsfield
★ 5 (1)
Autumn Hill Lakehouse
🏆 Pride Points x3
Wi-Fi • Hot tub • Parking
Friendly
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
Approval 
Instant
Entire place • 8.3 miles from Pittsfield
Picturesque Cottage with Sunroom on Ashmere Lake!
🏆 Pride Points x3
Wi-Fi • Parking • Private beach
Friendly
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
Approval 
Instant
Entire place • 8.4 miles from Pittsfield
Lakefront Hinsdale Home about 10 Mi to Pittsfield!
🏆 Pride Points x3
Wi-Fi • Parking
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