A historic building with classical architecture, a traffic light, and a yellow taxi.

Gay friendly Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Gay friendly Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Pittsfield LGBT-friendly hotels

A building entrance with a large planter with purple flowers and a small tree.
A library with bookshelves, a television, and two armchairs.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.
A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

1. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
P7,015
P7,836 total
includes taxes & fees
Nov 1 - Nov 2
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A spacious living room with a large sofa, a coffee table, and a fireplace.

2. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
P8,028
P8,967 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
Room
A conference room with a whiteboard, tables, and chairs.
An indoor swimming pool with clear pool rules signage, multiple seating areas, and a view of the outdoors through large windows.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

3. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Mark
P6,152
P6,872 total
includes taxes & fees
Nov 6 - Nov 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
Living area
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

4. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
P7,207
P8,050 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn & Suites Berkshires-Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A covered outdoor area with stone pillars and a view of a road and green hills.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
P7,885
P8,808 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A modern living room with a fireplace, comfortable seating, and a large window with curtains.
A dining area with a glass table, red walls, and framed artwork.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
P9,633
P11,049 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
P8,600
P9,435 total
includes taxes & fees
Nov 1 - Nov 2
Shaker Mill Inn
A modern hotel lobby with seating areas, tables, and a reception desk.
A kitchenette with a microwave, coffee maker, and coffee cups.
A breakfast area with a counter, coffee machine, and a display of pastries.
A coffee station with two coffee machines and a variety of coffee pods and cups.

8. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
United States
Maria Dulce
P6,403
P7,152 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

9. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
United States
Jared
P7,329
P9,411 total
includes taxes & fees
Oct 13 - Oct 14
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.

10. Sunset Inn

Sunset Inn
Lee
United States
Lauren
P5,283
P5,901 total
includes taxes & fees
Oct 26 - Oct 27
Sunset Inn
View all properties

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?
Hotel On North is a top LGBTQ-friendly hotel that features free WiFi and free parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Hilton Garden Inn Lenox Pittsfield are other good choices for your stay.
How many gay-friendly accommodations are there in Pittsfield?
You'll find 3 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 Bousquet Ski Area. While you're here, create some great memories of your trip with stops at Hancock Shaker Village, Housatonic River, and Barrington Stage Company.
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.

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