Find Gay friendly Hotels in Cheshire, MA

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Check availability on Cheshire Gay friendly Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Cheshire LGBT-friendly hotels

Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is ￥33,663
￥35,581 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Harbour House Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1003)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is ￥13,809
￥15,425 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (439)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ￥17,700
￥19,417 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Shaker Mill Inn
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (592)
"Cute place"
United States
Lisa
The price is ￥15,500
￥17,313 total
includes taxes & fees
Dec 30 - Dec 31
Maple Terrace Motel
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel
3.0 star property
North Adams
8.8 out of 10, Excellent, (1001)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ￥19,344
￥21,607 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Hotel Downstreet, an Ascend Collection Hotel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Very comfortable beds! "
United States
Gerald
The price is ￥16,033
￥17,909 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Berkshires-Lenox
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ￥20,022
￥22,364 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield
Seasonal outdoor pool
Sunset Inn

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
The price is ￥14,091
￥15,740 total
includes taxes & fees
Dec 30 - Dec 31
Sunset Inn
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown
2.5 star property
Williamstown
8.8 out of 10, Excellent, (396)
"our stay was great."
United States
nathaniel
The price is ￥24,581
￥27,457 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Fairfield Inn & Suites by Marriott Williamstown
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (594)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is ￥21,763
￥24,310 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Courtyard by Marriott Lenox 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.
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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.
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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