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Gay Accommodations & Gay Bnbs in Pittsfield
Stay where you never have to explain yourself
Hosted by Michael
Entire place • Pittsfield
Booked 1 time
5 (1)
The Oliver Wendell Holmes Guest Cottage Holmesdale
1 Bedroom • 2 Beds • 1 Bathroom
Joseph·5·Aug. 2025· "Lovely spot to stay in the Berkshires. The pool was great and the hosts are very nice. There's a lot to do in the area and the cottage was very comfortable."
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Keep searching in the city: Trusted gay-friendly stays
Gay travel is a niche market, which is why our inventory here is sometimes limited. By booking one of these LGBTQ+ friendly stays, you directly help misterb&b fund its mission: recruiting new gay hosts and covering the complex legal and regulatory costs we face. Give your stay meaning - book your favorite below!
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Instant bookingHotel ** • Pittsfield
4.36 (1)
Berkshire Inn
Wi-Fi • Pool • Parking
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel *** • Pittsfield
4.44 (1)
Best Western Plus Berkshire Hills Inn & Suites
Wi-Fi • Parking • Gym
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel • Pittsfield
4.44 (1)
The Central Downtown Inn Suites
Wi-Fi • Parking • Pets allowed
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel • Pittsfield
4.04 (1)
Heart of the Berkshires Motel
Wi-Fi • Parking • Pets allowed
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel ** • Pittsfield
5 (1)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Wi-Fi • Pool • Hot tub
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel *** • Pittsfield
4.72 (1)
Hilton Garden Inn Lenox Pittsfield
Wi-Fi • Pool • Hot tub
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel *** • Pittsfield
3.2 (1)
Fairbridge Inn Express Pittsfield
Wi-Fi • Parking • Smoking allowed
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Hotel **** • Pittsfield
4.84 (1)
Berkshire Mountain Lodge
Wi-Fi • Pool • Hot tub
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Pittsfield
5 (1)
Spacious Historic Home in the Berkshires!
5 Bedrooms • 5 Beds • 2 Bathrooms
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Pittsfield
5 (1)
Elegant Pittsfield Home Near Downtown & Skiing!
5 Bedrooms • 5 Beds • 4 Bathrooms
Certified Gay-FriendlySigned a non-discrimination policy.
Instant booking
Entire place • Pittsfield
Lake Views & Dock Access - Pittsfield Cottage!
4 Bedrooms • 6 Beds • 2 Bathrooms