A lake surrounded by autumn-colored trees and hills.

Gay friendly Hotels in Cheshire, Massachusetts

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Check availability on Cheshire Gay friendly Hotels

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Cheshire LGBT-friendly hotels

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.
A room with a large sliding glass door leading to a garden. Inside, there is a table with chairs and a small table with a vase.
A spacious living room with a large window, a sofa, a chair, and a dining area.
A gazebo in a lush garden with flowering plants and a large tree.

1. Harbour House Inn

Harbour House Inn
Cheshire
United States
Gregory
P15,926
P16,834 total
includes taxes & fees
Oct 22 - Oct 23
Harbour House Inn
A building entrance with a large planter with purple flowers and a small tree.
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.
A library with bookshelves, a television, and two armchairs.

2. Hotel On North

Hotel On North
Pittsfield
United States
Lawrence
P6,312
P7,051 total
includes taxes & fees
Nov 3 - Nov 4
Hotel On North
A garden with a swing set, a blue chair, and a flower bed.
A swimming pool with lounge chairs and a fence.
A house with a porch, snow-covered ground, and a Christmas tree with lights.
A garden with a wooden pergola, potted plants, and a lawn with chairs.

3. Maple Terrace Motel

Maple Terrace Motel
Williamstown
United States
Deborah
P6,214
P6,940 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.
A modern cafe with a wooden accent wall, a coffee machine, and black chairs.
A modern interior with a large window, a wooden table, and bar stools.
A reception area with a large landscape painting, a dark reception desk, and a potted plant.

4. Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
North Adams
United States
Augusta
P7,481
P8,357 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Downstreet, an Ascend Collection Hotel
Room
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
A conference room with a whiteboard, tables, and chairs.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

5. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
United States
Mark
P6,151
P6,870 total
includes taxes & fees
Nov 6 - Nov 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A sign for 'The 1896 House' with a logo for Brookside Accommodations.
A white two-story house with a sloped roof, large windows, and a small porch.
A pool area with a white building, a fence, and trees in the background.
A covered porch with white furniture and green chairs, surrounded by lush greenery.

6. 1896 House Country Inn & Motels

1896 House Country Inn & Motels
Williamstown
United States
Maryann
P6,669
P7,449 total
includes taxes & fees
Oct 11 - Oct 12
1896 House Country Inn & Motels
A modern living room with a fireplace, comfortable seating, a flat-screen TV, and a stone accent wall.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A reception area with a wooden reception desk, a bar area in the background, and a decorative wall piece.
A fire feature with a metal frame and a brick wall in the background.

7. Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
Williamstown
United States
C. David
P9,549
P10,667 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Williamstown
A spacious hotel lobby with multiple seating areas, large windows, and a television.
Living area
A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

8. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Thomas
P7,149
P7,985 total
includes taxes & fees
Nov 7 - Nov 8
Hampton Inn & Suites Berkshires-Lenox
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 spacious living room with a large sofa, a coffee table, and a fireplace.
A hotel patio with outdoor seating and a fire pit.

9. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
James
P8,026
P8,965 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Lenox Pittsfield
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.
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

10. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
United States
Tracy
P7,884
P8,806 total
includes taxes & fees
Nov 5 - Nov 6
Courtyard by Marriott Lenox Berkshires
View all properties

Top Cheshire Hotel Reviews

Frequently asked questions

Looking for an LGBTQ-friendly hotel in Cheshire?
If you're searching for a place where you'll feel welcome in Cheshire, Expedia has all the gay-friendly hotels you'd wish for. Discover the people, places, and traditions found only in Cheshire.
What's the best LGBTQ-friendly accommodation in Cheshire?
Harbour House Inn is a top LGBTQ-friendly B&B, and features free breakfast and free WiFi.
What are the top places to visit in Cheshire?
During your vacation, get out and discover all that Cheshire is known for. You and your traveling companions may want to visit Mount Greylock State Reservation and Cheshire Reservoir.
What is a gay-friendly hotel in Cheshire?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual, and transgender travelers are proudly welcomed. We have worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of gay-friendly hotels worldwide. In Cheshire, hotels affiliated with IGLTA operate in a spirit of inclusiveness, prioritizing a diverse environment in which guests are welcomed, respected, and not obliged to declare or hide their sexual orientation.
What can I expect from a gay-friendly hotel in Cheshire?
Take a vacation from the ordinary; stay at a gay-friendly hotel in Cheshire, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer concierge services that provide information about nearby LGBTQ restaurants and local events.

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