Find Gay friendly Hotels in Cheshire, MA

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Check availability on Cheshire Gay friendly Hotels

Tonight
Dec 4 - Dec 5
Tomorrow
Dec 5 - Dec 6
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Cheshire Gay friendly Hotels

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"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!! "
United States
Lorie
The price is ₩384,626
₩406,549 total
includes taxes & fees
Dec 8 - Dec 9
Harbour House Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is ₩159,833
₩175,338 total
includes taxes & fees
Dec 7 - Dec 8
Shaker Mill Inn
Restaurant
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, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ₩135,397
₩151,238 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hypo-allergenic bedding, desk, laptop workspace, blackout drapes
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
North Adams
8.8 out of 10, Excellent, (1000)
"Great property, nice staff, lovely rooms, awesome location."
Canada
Krysten
The price is ₩157,047
₩175,421 total
includes taxes & fees
Dec 20 - Dec 21
Hotel Downstreet, an Ascend Collection Hotel
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ₩151,328
₩169,034 total
includes taxes & fees
Dec 14 - Dec 15
Hampton Inn & Suites Berkshires-Lenox
Seasonal outdoor pool
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 ₩131,972
₩147,413 total
includes taxes & fees
Dec 6 - Dec 7
Sunset Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (794)
"Place was great!"
United States
Benjamin
The price is ₩156,167
₩203,105 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (657)
"Clean and convenient to Mt. Greylock. Kind staff. "
United States
Kristen
The price is ₩151,328
₩169,034 total
includes taxes & fees
Dec 14 - Dec 15
Hilton Garden Inn Lenox Pittsfield
Exterior detail
Maple Terrace Motel

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (586)
"Reception was great, lovely beds (most important to me), great location, this place is excellent."
United States
William
The price is ₩145,170
₩162,150 total
includes taxes & fees
Dec 7 - Dec 8
Maple Terrace Motel
Exterior
Fairfield Inn & Suites by Marriott Williamstown

Fairfield Inn & Suites by Marriott Williamstown

2.5 star property
Williamstown
8.8 out of 10, Excellent, (394)
"our stay was great."
United States
nathaniel
The price is ₩230,219
₩257,156 total
includes taxes & fees
Dec 9 - Dec 10
Fairfield Inn & Suites by Marriott Williamstown
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

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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.