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

Pittsfield Gay friendly Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Gay friendly Hotels

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

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 lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.
A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

1. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
RM457
RM510 total
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.
A hotel patio with outdoor seating and a fire pit.

2. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
RM522
RM584 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Lenox Pittsfield
Room
A conference room with a whiteboard, tables, and chairs.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
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
RM400
RM447 total
includes taxes & fees
6 Nov - 7 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A spacious hotel lobby with multiple seating areas, large windows, and a television.
A hotel with a brick facade, a covered entrance, and an American flag.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
Exterior

4. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
RM469
RM524 total
includes taxes & fees
4 Nov - 5 Nov
Hampton Inn & Suites Berkshires-Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
RM513
RM573 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A dining area with a glass table, red walls, and framed artwork.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
RM627
RM719 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.
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.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
RM560
RM614 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
A modern hotel lobby with seating areas, tables, and a reception desk.
A hotel room with two beds, a desk, a TV, and a window with curtains.
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
RM417
RM465 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
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.

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
RM478
RM614 total
includes taxes & fees
12 Oct - 13 Oct
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 covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A hotel room with two beds, a chair, and a bedside table with a phone.

10. Sunset Inn

Sunset Inn
Lee
United States
Lauren
RM344
RM384 total
includes taxes & fees
26 Oct - 27 Oct
Sunset Inn
View all properties

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?
Hotel On North is a top LGBTQ-friendly hotel that features free Wi-Fi and free parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Hilton Garden Inn Lenox Pittsfield are other good choices for your holiday.
How many gay-friendly accommodation options are there in Pittsfield?
You'll find 3 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 Barrington Stage Company.
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.

Explore a world of travel with Expedia