Find Gay friendly Hotels in Pittsfield, MA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Gay friendly Hotels

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Pittsfield Gay friendly Hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (846)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is NT$3,447
NT$3,850 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel Downstreet, Ascend Hotel Collection
Hypo-allergenic bedding, laptop workspace, blackout drapes

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1005)
"Clean,friendly staff and great location."
The price is NT$4,306
NT$4,809 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Downstreet, Ascend Hotel Collection
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is NT$4,556
NT$5,089 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Good lodgings in a great area to visit."
The price is NT$4,306
NT$4,809 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NT$4,762
NT$5,319 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Garden Inn Lenox Pittsfield
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (684)
"Had a great time"
The price is NT$3,573
NT$4,409 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (28)
"Nice , new , quiet and clean room. Bed was very comfortable . Missed the human touch of having a traditional office to call when lost and ideas where to eat, etc. "
The price is NT$4,615
NT$5,155 total
includes taxes & fees
Sep 1 - Sep 2
East Rock Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (723)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is NT$4,766
NT$5,323 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Maple Terrace Motel
Exterior detail

Maple Terrace Motel

2.5 star property
9.6 out of 10, Exceptional, (567)
"The staff, room and property was wonderful! "
The price is NT$3,372
NT$3,766 total
includes taxes & fees
Aug 17 - Aug 18
Maple Terrace Motel
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is NT$3,995
NT$5,634 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
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 an LGBTQ-friendly hotel in Pittsfield?
If you're searching for a place where you'll feel welcome in Pittsfield, Expedia has all the gay-friendly hotels you'd wish for. Visitors are sure to enjoy all Pittsfield has to offer including its entertainment venues.
What is the favorite LGBTQ-friendly place to stay in Pittsfield?
Holiday Inn & Suites Pittsfield-Berkshires by IHG is a top LGBTQ-friendly hotel, and features free WiFi and free internet. Hilton Garden Inn Lenox Pittsfield is another good choice for your stay.
How many gay-friendly accommodations are there in Pittsfield?
You'll find 2 gay-friendly hotels in Pittsfield.
What should I see while I'm in Pittsfield?
During your vacation, get out and enjoy all that Pittsfield has to offer. You and your traveling companions may want to visit Berkshire Museum, Colonial Theater, and Barrington Stage Company. While you're here, create some great memories of your trip with stops at Bousquet Ski Area, Hancock Shaker Village, and Housatonic River.
What is an LGBTQ-friendly hotel in Pittsfield?
LGBTQ-friendly hotels welcome all travelers who identify as LGBTQIA+. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Pittsfield, hotels affiliated with IGLTA will provide lesbian, gay, bisexual, and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from an LGBTQ-friendly accommodation in Pittsfield?
Stay at an LGBTQ-friendly hotel in Pittsfield and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodations offer wedding ceremonies and honeymoon packages for same-sex couples.