Search Gay-Friendly Hotels in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Gay-Friendly Hotels

Our top choices for Pittsfield LGBT-friendly hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (989)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is Rp1.547.534
Rp1.728.595 total
includes taxes & fees
22 Dec - 23 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (658)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is Rp2.134.829
Rp2.384.571 total
includes taxes & fees
3 Jan - 4 Jan 2026
Hilton Garden Inn Lenox Pittsfield

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is Rp1.822.807
Rp1.999.619 total
includes taxes & fees
21 Dec - 22 Dec
Shaker Mill Inn

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
United States
regina maria
The price is Rp1.789.361
Rp1.998.716 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is Rp1.752.570
Rp1.957.622 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Berkshires-Lenox

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is Rp2.087.365
Rp2.331.587 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hotel Downstreet, an Ascend Collection Hotel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (590)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is Rp1.652.706
Rp1.846.023 total
includes taxes & fees
20 Dec - 21 Dec
Maple Terrace Motel

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is Rp3.589.210
Rp3.793.878 total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is Rp2.253.690
Rp2.517.372 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is Rp2.030.575
Rp2.594.520 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Top Pittsfield Hotel Reviews

Frequently asked questions

Searching for LGBTQ-friendly accommodation in Pittsfield?
If you're looking for a place where you'll feel at ease in Pittsfield, our website has the gay-friendly hotel you're looking for. Visitors are sure to enjoy all Pittsfield has to offer including its entertainment venues.
What's the best LGBTQ-friendly place to stay in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top LGBTQ-friendly hotel, and features free Wi-Fi and free Internet. Hilton Garden Inn Lenox Pittsfield is another good choice for your holiday.
How many gay-friendly accommodation options are there in Pittsfield?
You'll find 2 gay-friendly accommodation options in Pittsfield.
What should I see while I'm in Pittsfield?
During your trip, get out and enjoy everything Pittsfield has to offer. You and your travelling companions may want to visit Berkshire Museum, Colonial Theater and Bousquet Ski Area. While you're here, create some great memories of your trip with stops at Hancock Shaker Village, Housatonic River and Berkshire Athenaeum.
What is an LGBTQ-friendly hotel in Pittsfield?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers are proudly welcomed. You'll find a selection of LGBTQ-friendly accommodation options on our site. In Pittsfield, these hotels will provide lesbian, gay, bisexual and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from LGBTQ-friendly accommodation in Pittsfield?
Stay at a gay-friendly hotel in Pittsfield and you won't have to hide your same-sex relationship or your sexuality when you check in. Many of our LGBTQ-friendly accommodation options offer concierge services that provide information about nearby LGBTQ restaurants and local events.