Gay friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Gay friendly Hotels

Tonight
Jul 5 - Jul 6
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Jul 6 - Jul 7
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Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20

Top Pittsfield Gay friendly Hotels

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (813)
"Clean rooms Staff was very friendly and helpful "
The price is P6,940
P7,752 total
includes taxes & fees
Jul 13 - Jul 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (636)
"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 P12,677
P14,160 total
includes taxes & fees
Jul 13 - Jul 14
Hilton Garden Inn Lenox Pittsfield
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, (1004)
"Fantastic place"
The price is P8,106
P9,054 total
includes taxes & fees
Aug 4 - Aug 5
Hotel Downstreet, Ascend Hotel Collection
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (50)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is P14,801
P15,644 total
includes taxes & fees
Jul 8 - Jul 9
Harbour House Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (386)
"No frills but it was a great stay!"
The price is P5,360
P5,988 total
includes taxes & fees
Jul 7 - Jul 8
Sunset Inn
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, (665)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is P8,702
P10,508 total
includes taxes & fees
Jul 9 - Jul 10
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 P11,463
P12,804 total
includes taxes & fees
Jul 13 - Jul 14
Hampton Inn & Suites Berkshires-Lenox
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (559)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is P11,962
P13,362 total
includes taxes & fees
Jul 13 - Jul 14
Courtyard by Marriott Lenox Berkshires
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, (1001)
"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 P8,468
P11,665 total
includes taxes & fees
Jul 21 - Jul 22
The Cornell Inn, Lenox & The Berkshires
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (475)
"All was just as advertised and the family/staff was friendly and helpful. "
The price is P9,187
P10,262 total
includes taxes & fees
Jul 7 - Jul 8
Whistler's Inn Bed & Breakfast
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.

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.